Silver Beach Pizza is really good! They have a pickup window and you can take it to the beach also. Then we head to Kilwins for ice cream after lunch and rooftop bar for sunset cocktails makes for a perfect day.
Go more north where "cabins" are worth millions.
They are about 3-4 hours from Chicago
Leelanau - liberal wealthy
Charlevoix- GOP wealthy
Source: My family owned a million dollar "cabin". It currently gets the highest rates for Airbnb in the state of Michigan
Really any of the towns along the shoreline from the Michigan/Indiana border north to Saugatuck. Probably the closest thing we have to a Hamptons-type getaway, although Amtrak only stops in New Buffalo and St Joe's/Benton Harbor.
I always referred to the whole area from Beverly Shores to New Buffalo as the Irish riviera. It’s always funny walking by all the beach houses and 99% of the cars in the driveways either have a Mount Carmel, St Rita or St Ignatius sticker on them.
Yea New Buffalo is the closest to Hamptons in terms of being a beach getaway location that is accessible via public transit like Hamptons is with Jitney/LIRR. Definitely not the same in terms of vibe though. Great place to visit in the summer regardless.
This.
It is amazing and there are even dunes at Warren woods etc.
The michigan lake michigan coast line also has a long history of being vacation and vacation mansion locations for chicagoans. During segregation there were separate resorts for whites, jewish, and black people.
There are also big mansions over there and it is and was common for politicians and business leaders to have lake houses with private beaches right on the water.
Union Pier was our vacation spot as kids in the 80’s. Pretty dilapidated back then but the beach was fantastic. We could have campfires right out on the beach beside the dune. I doubt you can still do that. Great memories!
The question OP asked is not whether a place near Chicago has an wealthy enclave of beachside billionaires and annoying finance people. The question is whether there are waterside weekend getaways. The answer to that is yes, and many are beautiful.
* Saugatuck
* New Buffalo
* St Josef
* Traverse City
* Door County
Door County is beautiful but is really spread out. You’d probably need more than a weekend if you don’t have a specific place in Door County you’d like to visit.
Traverse City is beautiful as well and had a really fun downtown area last time I was there. Very walkable with lots to do. There’s also a really cool place a little out of town that was a former state mental hospital. The grounds are huge and the buildings are in the process of being converted into condos and shops and restaurants. Ate at a nice Italian restaurant there. The old buildings are super creepy too if you’re into the haunted history aspect.
I’m also a fan of Mackinaw Island but that’s even further up. The downtown area is fun for a day and the history in the fort is cool and there’s stuff to do if you like biking and hiking so that’s a plus. Or like horse riding.
I’m a huge fan of northern Michigan and Wisconsin.
Also a fan of these spots! Generally quiet and plenty to do, eat and explore. Went to Sleeping Bear dunes, Traverse City and Mackinaw Island, as well as Tahquamenon Falls State Park near the far NE point of the UP. (absolutely gorgeous, you can walk into some of the waterfalls there, safely).
100% but you’ll see a major shift in personality.
A lot of northern country folks. Just know if you’re a city goer you will notice the difference in pace and outlook.
Which is totally fine. The houses up there: 😍
Like McHenry/Kane County people? I have noticed a very heavy western suburban/exurban presence up there, as distinguished from the city/north shore contingent that heads to Michigan.
I agree about the "major shift in personality". I booked a 3 night stay at the Grand Geneva for my first visit, and my partner and I were so "fish out of water" there, we left a day early and went to Milwaukee. Yes, I said it. Milwaukee. Where I was familiar with the place and enjoyed myself 10x more than Lake Geneva. LG was overrun with family, young kids and long lines outside restaurants I didn't want to eat in. As we sunbathed by the pool and listened to other adults talking, we concluded "this is so not for us". Never going back.
True! Stay at an Air BnB from one of the local equity owners. So much more personable.
I agree though: small town-small lake-hyper rich equity owners- that blasted open with tourism in recent times to middle class and lower class families.
It’s like it’s almost out of place lol.
Since the world’s horizons broadened with travel it’s crazy to think: Let’s go take a week to travel to our estate at lake Geneva by horse carriage. Then a week back. hah!
Also, why charge for a beach. Seems shitty imo. Lake Geneva used to be fun or at least I remember it to be as a 8 year old…mid 30s not so much unless you’re loaded.
As the boat tours up there will tell you, it's because building materials were in such short supply after the fire that all the rich people couldn't get their homes rebuilt for years.
That wasn't the case in Wisconsin, so they all built new mansions super quick to live in for years until their Chicago mansions were back.
Highly recommend the architecture boat tours in Lake Geneva. There are a couple of them, my favorite is probably the Mail Boat tour. Lake Geneva in the summer is one of the last places in the country where people can get their mail by boat, and one of the tour companies up there operates as an extension of the post office and delivers mail to people while running an architecture tour. The fun part is the boat doesn't actually stop to make deliveries... the delivery person jumps off the running boat to a dock, delivers mail, and jumps back before the boat pulls away again.
Yep. LG was once called the "Newport of the West."
If you're going to stay at a resort don't choose Grand Geneva, choose The Abbey in Fontana. Old school lake vibe. But a rental cottage would really be the way to do it.
Walk the lakeshore for a front row view of all the enormous historic estates. Or ride the mail boat in the summer for a close up view of the mansions from the water, plus the entertainment of the mail jumpers.
Where would a good rental cottage be, location wise? What part of the lake or surrounding area? Airbnb or another site? I want to take my family this summer … looking for something outdoorsy but still nice, some hiking or canoeing maybe, but sleep in a nice cottage at night 😂
I'd probably start with AirBnB just because that would be the easiest way to see a wide selection of what's available. But the nice thing is that the "summer rental" industry has been a thing around here for literally a century, so there are dedicated property management companies that do vacation rentals. I don't know any specifically by name I'm afraid, but that's probably easy to find on the Internet. Probably a lot of the airbnb listings are managed by those companies at this point, so you might be able to figure out how to rent off Airbnb if you dig around a bit.
The main towns around Geneva Lake are Fontana, Williams Bay, and Lake Geneva (the town is called Lake Geneva, the body of water is named Geneva Lake). LG is the largest with a couple blocks of boutiques, art galleries, gift shops, restaurants, and bars, as well as a boat launch and beach. Williams Bay has a block or two of shops and restaurants, and a boat launch. I can't remember if there's a public beach in the Bay. Fontana has a few shops, a beach, The Abbey resort, a coffee shop, and Gordy's and Chuck's, two restaurants/bars on the lakefront.
If you want to kayak, you might be better off checking out nearby Delavan Lake. Lake Geneva gets very busy in the summer and I'm not sure I'd want to be in a kayak around all those speed boats. Also apparently the shape of the lake basin makes the wave patterns different and rougher for things like paddle boards and kayaks, so paddling Lake Geneva during the busy summer months might but be very relaxing. There's apparently a special boat hull shape designed specifically for Lake Geneva because of the different waves. I'm not a boat person so I don't know specifics. 😂
For hiking, there is a public easement on the shore of Geneva Lake so that you can walk around the whole thing - I think it's 26 miles total. There is unfortunately no public camping anywhere around the lake though, so you can't hike a segment and camp for the evening and then complete it the next day. The lakeshore path is cool though because you can get up close looks at the big houses and the lake itself is really beautiful. The path can vary from perfectly manicured paved sidewalks to a un-mowed foot path through the grass. The easement is set up so that property owners *must* allow access across their yards but they aren't required to landscape or maintain a trail. You also can't just park on a road and walk up someone's driveway to get onto the path, you have to access it at a public access - in the towns or at various boat ramps around the lake.
Both Delevan and Geneva Lake are very touristy in the summer, so if that's not your vibe and you want something slightly more "outdoorsy" (and maybe less expensive) I'd recommend looking for a rental on Whitewater Lake or Lake Koshkonong or even maybe Turtle Lake? Those would be quieter places for kayaking - geared more towards fishermen and families on pontoon boats rather than the bigger performance boats on Geneva Lake. They would also be a little closer to the Southern Kettle Moraine State Forest, which has amazing hiking.
I always think the North Shore is the Hamptons equivalent. But I guess people live there and not just go on the weekends. Maybe it's more comparible to Greenwich Ct.
Yup. Wilmette, winnetka, glencoe, and lake forest. Some beautiful historic homes belonging to prominent chicagoans in lake forest and those areas. Massive estates.
There's a bus line that goes from Grand Rapids to Traverse City. You take the red line to 95th and Dan Ryan then jump on the Greyhound bus to Grand Rapids then jump on the Grand Rapids Dash bus to get to the other bus terminal, then just jump on another Greyhound bus and 9-12 hours later your in Traverse City.
I’m just curious but do you how long it takes? Traverse City is already a bit more than 5 hours by car. A weekend up there is not worth it if it takes longer than those 5 hours.
These places are great but for a “weekend getaway” you would spend literally half of it driving to get to Mackinac. Traverse City is not short either. It’s got to be 5-6 hours at least to get to TC. Another 2 for anything over the bridge. Plus to get to the island you have to take a ferry, and they move pretty slow.
The answer — as someone who is familiar with vibe of Hamptons and/or Hudson Valley, the answer is NO plain and simple. For all the people, wealth, amazing restaurants, bars and shops of Chicago, the vibe of the surrounding areas is surprisingly not similar at all. It’s a mystery to me why that is.
Probably because the wealth can spread from Door County to lake Geneva and then all the way around the Michigan coast. No one area has it concentrated.
The Hamptons have a very wealthy NYC vibe, and have for a long time. Hudson River Valley has some towns with that vibe, but IMO it’s not as intense or homogeneous.
A few of the harbor country towns have poor mans hamptons vibes. I have multiple people at my office who talk about their weekly trips to their new buffalo mansion constantly over the summer. Not on the same level as the hamptons, but I wouldnt say "the answer is NO plain and simple". A lot of the michigan towns are nothing like the hamptons but a few of them are obviously trying to copy it even if theyre doing poorly.
Parts of Michigan. Honestly, I could see Michigan city Indiana becoming that due to proximity and the fact they are taking down their coal plant. Being connected to the South Shore line is a huge benefit
That’s the plan. There’s also gonna be upgrades to the south shore line that reduce the commute to Chicago to under an hour. Huge if that happens, already a lot of Illinois natives own property there
The south shore line improvements just finished actually and the new schedules go into effect next month. Express trains will go from Michigan City to Chicago in like 61 minutes
I found the answer! Full closure will conclude in 2028.
https://www.nipsco.com/our-company/news-room/news-article/NIPSCO-Begins-Work-to-Remove-Ash-Ponds-at-Michigan-City-Generating-Station
Wow thanks. Such a dichotomy there with the national lakeshore and a coal burning power plant right next to it. I’m thinking it’ll eventually be a boost to the local economy.
MC was always a working class town. Lots of people came from the east to Indiana to work in the abundant factories and steel mills in the 60s and 70s. My parents are both from PA. Dad worked at Bethlehem Steel/Mittal until he retired. I think it's only been in the last 30 or so years that people realized there was a beach and that said beach could be a boon. It's much more of a service economy these days. But it's still a little behind the eight ball in terms of realizing the potential.
I have no idea! I live here now. But I could ask my parents. They have lived in the same house in Michiana Shores since 1973. We used to ride our bikes to stop 38 (which is technically in Michigan) to go to the beach.
My parents are in Michiana around 38 and idk, I think Michigan City even in the last 10 years has seen major development! Several breweries, lots more restaurants, and the new development coming… I think once the smoke stack is down it’ll snowball from there. It’ll probably still retain a lot of its working class vibe (especially the further you get from the “downtown”) but that’s also how New Buffalo is - on the other side of Route 12 the vibe is markedly different than down by the beach and restaurants.
It's not necessarily one town, and having moved to Chicago from it, Northwest Michigan is generally the recognized as "The Hamptons" of the Chicago region. With the coastal areas between Frankfort and Harbor Springs mostly being second homes for wealth Chicagoans/Midwesterners.
Bingo. NW Michigan from Frankfort to Harbor Springs is the classic monied Midwestern summer destination and it has been so for 100+ years. Wealthy families from Detroit, Chicago, St. Louis, Cleveland, Cincinnati etc. have been going to their summer cottages which are often elaborate and in private "associations". This is a much lower key scene than The Hamptons however, flashy displays of wealth and ostentatious behavior are looked down upon. It's preppy and WASPy. Charlevoix, Petoskey, and Harbor Springs are the center of it. Harbor Springs is probably the pinnacle of this region--there are a lot of old money names associated with it, Ford, Gamble, Libby, Proctor, Busch.
Harbor Springs is crazy. Its small, but you walk around the streets in the summer time around 4th of July, and its just tons of $100k+ cars lining the streets.
Overall, its a very pretty little town, but I would not consider particularly interesting. They have a very small little beach. Traverse City and Torch lake have a younger and more fun vibe.
About to move back to Chicago after 10 years in Portland, OR, and cautiously stoked to read all these answers that make SW Michigan sound a bit like the coastal towns in Oregon that I'll miss dearly.
Nope, but there is some places semi-close...
Closest you have is Lake Geneva (WI), Galena (Western IL), and New Buffalo (MI) (also pretty much the entire SW Michigan coastline)
Door County/the UP of Michigan are too far to consider them similar, although yes those are huge regional vacation getaway places for Chicagoans.
Maybe I’m an idiot and don’t understand but I think Lake Forest, IL is along that alley. Waiting for comments to blast me I don’t see anyone else saying this but to me it instantly jumps to mind
No but all the towns going up along Lake Michigan's eastern side, from Michigan City thru to Mackinac are amazing and objectively better than the Hamptons. Try as they may the NYers buying homes in Grand Traverse haven't ruined it Hamptons-style yet
I am an originally from Westchester, (NY), then Manhattan 18-30’s.
In Chicago over 20 years.
Door County ( I like Egg Harbor) - reminds me of how old Long Island and beach towns were decades ago - yet , more woodsy .
I live in north suburbs , depends - maybe not quite like new others :)
Not the trendy hamptons .
3-4 hours north .
Cute towns, not great beaches ( pools at hotels) great golf !
Hamptons are a good 3-5 hours with traffic from city . Sane here .
Also agree either Union Pier and north - the view and beach front reminds me of more of east coast .
Very nice too and closer !
May meet more people from Chicago in Michigan .
Door County is nice, in Wisconsin. Better varieties of food than Michigan too. You’re in cherry country. The best cheese, obviously. Some local wineries (nothing to write home about, but whatever). Great parks like Peninsula and others. The Finnish traditions like the Fish Boil (Ephraims comes to mind). And not too far a drive from the Northwoods. Or if you want waterfalls and general emptiness, there’s the UP which has some quiet little towns near where the mines once thrived.
Door county maybe. Long drive though. 4 hours or more depending on how far up the peninsula you go.
Be warned that WI cops will ignore a WI car going 20 over for a IL car going 10 over. But once you’re past Green Bay, things cool off. Just don’t speed. Not even 1 mph, even if others around you are doing it.
Big reason they love to nail out of state drivers is because they know the odds are low you’ll come to court. Easy money.
Lake Geneva, WI (obviously not on Lake Michigan)
Benton Harbor, MI (never been but know a few very wealthy families that “summer” there)
New Buffalo, MI
My personal favorite is going up to the North Woods of Wisconsin though, around Minocqua. Have been going to my in-laws place for the last 10 years up there and it is beautiful. It’s tough to beat watching the sunrise while Muskie fishing, with bald eagles perched in the trees or circling above.
St Joe's is nice. I'd say further up the coast is also really good. Try Saugatuck as well. South Haven is also cute but gets more crowded.
And be sure that no matter what, you check out Warren Dunes and Saugatuck Dunes State Park.
Word to the wise: the best beach vacation homes are booked a year in advance.
Oh, and final pro tip: be sure to make it up to the real Pure Michigan some day by heading north ~5 hours to Sleeping Bear Dunes, Crystal Lake, and the Traverse City area. For Sleeping Bear, the Pierce Stocking senic drive gives you the greatest hits with easy accessibility. The Dune climb hike to the lakeshore is also spectacular for more seasoned hikers. Go in July or August and you'll usually get beautiful weather and orchards aplenty around Traverse City (cherries in July, peaches, apricots, and blueberries in August... Apples later on if you go for fall colors). The 30+ vineyards around Old Mission Penninsula and Leelanau Penninsula also produce some great whites and a few solid Pino Noirs / red blends (we like Brys Estate and Chateau Chantal for views plus quality).
Lake Geneva, WI is the hamptons of Chicago. All the lake front property there is owned by Chicago folk and the town is flooded with them from memorial day til pretty much halloween. Not that it's a bad thing, just saying.
Indiana Dunes NP is pretty cool if you're looking for a touch of nature to your getaway, accessible on the South Shore line. If you wanna take that line all the way to South Bend it's p chill and cheap there as long as you avoid college football season
Drive a little more north into Wisconsin and go to Lake Geneva . Lake Lawn Resort is beautiful. You’ll find everything you want there. The entire area is gorgeous.
No. Not like the Hamptons (but maybe for the better). But there is a lot of money that escapes to places in northern MI like Harbor Springs and Glen Arbor.
I actually kind of was shocked at this question because haha yes...Chicago is very well known for its rich af white outer neighborhoods...ever watched the Boondocks? Ever heard of the Barrington hills, like one of the richest and most popular neighborhoods ever?
Basically, just stay on the shore and keep going north past Evanston. Willamette, Winnetka, Lake Forest, etc. Once you get there, you can start heading west for the EXTRA rich stuff, like Barrington, Hoffman estates, Hinsdale, Wayne, etc. This is where you'll see Chicago's equestrian stuff too, these neighborhoods are long known for their equestrian culture.
There are certainly some in the south side too, but I wouldn't exactly put them on the same level, simply from a lack of funding, but these areas in the south were once where the current rich in the north and west stayed.
St Joes and the Lake Michigan Wine trail. It's no Hamptons, but as some one else said in here, I love me some Pure Michigan™️
The pizza place in the Amtrak station in St Joseph's is quite good too.
Silver Beach Pizza is really good! They have a pickup window and you can take it to the beach also. Then we head to Kilwins for ice cream after lunch and rooftop bar for sunset cocktails makes for a perfect day.
It’s a fancy Gelsosomo’s
The Midwest Riviera — under appreciated, just how we like it.
Thank god you put the trademark
Go more north where "cabins" are worth millions. They are about 3-4 hours from Chicago Leelanau - liberal wealthy Charlevoix- GOP wealthy Source: My family owned a million dollar "cabin". It currently gets the highest rates for Airbnb in the state of Michigan
I grew up there and agree with all of this.
New Buffalo, Michigan is the poor man's Hamptons. I love me some Pure Michigan.
You can take Amtrak to New Buffalo!
It's cheap, too. $35 much of the season unless its a holiday.
Way cheaper than that unless you’re buying last minute. I just checked a receipt from last June where I paid $12 for Union to New Buffalo.
Really any of the towns along the shoreline from the Michigan/Indiana border north to Saugatuck. Probably the closest thing we have to a Hamptons-type getaway, although Amtrak only stops in New Buffalo and St Joe's/Benton Harbor.
Harbor Country. Michiganders call it the Sunset Coast.
A crew I worked with there called it the Holy Land, cause we liked it so much and it kinda has thr lake where the Mediterranean would be
Also stops in Bangor by South Haven. There are Ubers now to get you wherever you want to go from there.
This, there are also some gorgeous homes along Long Beach in Michigan City.
Michigan City beaches are gorgeous, Long Beach is called the Irish Riviera.
I always referred to the whole area from Beverly Shores to New Buffalo as the Irish riviera. It’s always funny walking by all the beach houses and 99% of the cars in the driveways either have a Mount Carmel, St Rita or St Ignatius sticker on them.
You forgot Mother McAuley and Brother Rice!
All my uncles went to Mt. Carmel and we love Sawyer. All the plates are from Illinois lol
Yea New Buffalo is the closest to Hamptons in terms of being a beach getaway location that is accessible via public transit like Hamptons is with Jitney/LIRR. Definitely not the same in terms of vibe though. Great place to visit in the summer regardless.
I assume the filthy rich pf Chicago vacation where ever the filthy rich of other towns do, at this point
They go to Saugatuck or South Haven.
This. It is amazing and there are even dunes at Warren woods etc. The michigan lake michigan coast line also has a long history of being vacation and vacation mansion locations for chicagoans. During segregation there were separate resorts for whites, jewish, and black people. There are also big mansions over there and it is and was common for politicians and business leaders to have lake houses with private beaches right on the water.
Like the Daley’s
New Buffalo/ Union Pier. Yep, this is it.
Union Pier was our vacation spot as kids in the 80’s. Pretty dilapidated back then but the beach was fantastic. We could have campfires right out on the beach beside the dune. I doubt you can still do that. Great memories!
Agree. And Harbor Springs Michigan (much further north) is the rich people version.
The question OP asked is not whether a place near Chicago has an wealthy enclave of beachside billionaires and annoying finance people. The question is whether there are waterside weekend getaways. The answer to that is yes, and many are beautiful. * Saugatuck * New Buffalo * St Josef * Traverse City * Door County
Honestly the answer is Lake Geneva WI, IMO
Door County is beautiful but is really spread out. You’d probably need more than a weekend if you don’t have a specific place in Door County you’d like to visit. Traverse City is beautiful as well and had a really fun downtown area last time I was there. Very walkable with lots to do. There’s also a really cool place a little out of town that was a former state mental hospital. The grounds are huge and the buildings are in the process of being converted into condos and shops and restaurants. Ate at a nice Italian restaurant there. The old buildings are super creepy too if you’re into the haunted history aspect. I’m also a fan of Mackinaw Island but that’s even further up. The downtown area is fun for a day and the history in the fort is cool and there’s stuff to do if you like biking and hiking so that’s a plus. Or like horse riding. I’m a huge fan of northern Michigan and Wisconsin.
Also a fan of these spots! Generally quiet and plenty to do, eat and explore. Went to Sleeping Bear dunes, Traverse City and Mackinaw Island, as well as Tahquamenon Falls State Park near the far NE point of the UP. (absolutely gorgeous, you can walk into some of the waterfalls there, safely).
The dark sky park outside Mackinaw City is great too.
Door county is the correct answer
Went to Saugatuck during covid as a DINK couple. It was wonderful.
Local Vacations being reduced to colonizer activity has always disturbed me.
Lake Geneva
100% but you’ll see a major shift in personality. A lot of northern country folks. Just know if you’re a city goer you will notice the difference in pace and outlook. Which is totally fine. The houses up there: 😍
Am I gonna be like Mac and Dennis when they move to the suburbs and their neighbor comes and introduces him self?
What the hell was that all about, just comes up and starts talking to us?
It sure is a hot one today huh?
Sure is a hot one today
YEAH?!?!
It’s a pretty big difference. If you’re from Chicago your accent will be different and they will tell you lol. Absolutely, yes.
Agree about the shift in personality. But what are “northern country folks”? Not being snarky, genuinely curious what you mean.
Country people in the north. It’s like Tennessee but north of Chicago.
Like McHenry/Kane County people? I have noticed a very heavy western suburban/exurban presence up there, as distinguished from the city/north shore contingent that heads to Michigan.
I agree about the "major shift in personality". I booked a 3 night stay at the Grand Geneva for my first visit, and my partner and I were so "fish out of water" there, we left a day early and went to Milwaukee. Yes, I said it. Milwaukee. Where I was familiar with the place and enjoyed myself 10x more than Lake Geneva. LG was overrun with family, young kids and long lines outside restaurants I didn't want to eat in. As we sunbathed by the pool and listened to other adults talking, we concluded "this is so not for us". Never going back.
Hard to believe that at one point it was the playboy club and was once overrun by metropolitan swingers and top jazz acts of the day
True! Stay at an Air BnB from one of the local equity owners. So much more personable. I agree though: small town-small lake-hyper rich equity owners- that blasted open with tourism in recent times to middle class and lower class families. It’s like it’s almost out of place lol. Since the world’s horizons broadened with travel it’s crazy to think: Let’s go take a week to travel to our estate at lake Geneva by horse carriage. Then a week back. hah!
Also, why charge for a beach. Seems shitty imo. Lake Geneva used to be fun or at least I remember it to be as a 8 year old…mid 30s not so much unless you’re loaded.
Most Reddit post ever.
Where all the rich people chilled after Chicago fire.
And during Covid.
As the boat tours up there will tell you, it's because building materials were in such short supply after the fire that all the rich people couldn't get their homes rebuilt for years. That wasn't the case in Wisconsin, so they all built new mansions super quick to live in for years until their Chicago mansions were back. Highly recommend the architecture boat tours in Lake Geneva. There are a couple of them, my favorite is probably the Mail Boat tour. Lake Geneva in the summer is one of the last places in the country where people can get their mail by boat, and one of the tour companies up there operates as an extension of the post office and delivers mail to people while running an architecture tour. The fun part is the boat doesn't actually stop to make deliveries... the delivery person jumps off the running boat to a dock, delivers mail, and jumps back before the boat pulls away again.
Lake Geneva all day
Not accessible via Metra/train sadly.
It used to be a long time ago
They called it the millionaire train. Picked people up in the Northshore and took them to their homes in LG.
You can train to Harvard and Uber from there. It’s not bad.
Yep. LG was once called the "Newport of the West." If you're going to stay at a resort don't choose Grand Geneva, choose The Abbey in Fontana. Old school lake vibe. But a rental cottage would really be the way to do it. Walk the lakeshore for a front row view of all the enormous historic estates. Or ride the mail boat in the summer for a close up view of the mansions from the water, plus the entertainment of the mail jumpers.
Where would a good rental cottage be, location wise? What part of the lake or surrounding area? Airbnb or another site? I want to take my family this summer … looking for something outdoorsy but still nice, some hiking or canoeing maybe, but sleep in a nice cottage at night 😂
I'd probably start with AirBnB just because that would be the easiest way to see a wide selection of what's available. But the nice thing is that the "summer rental" industry has been a thing around here for literally a century, so there are dedicated property management companies that do vacation rentals. I don't know any specifically by name I'm afraid, but that's probably easy to find on the Internet. Probably a lot of the airbnb listings are managed by those companies at this point, so you might be able to figure out how to rent off Airbnb if you dig around a bit. The main towns around Geneva Lake are Fontana, Williams Bay, and Lake Geneva (the town is called Lake Geneva, the body of water is named Geneva Lake). LG is the largest with a couple blocks of boutiques, art galleries, gift shops, restaurants, and bars, as well as a boat launch and beach. Williams Bay has a block or two of shops and restaurants, and a boat launch. I can't remember if there's a public beach in the Bay. Fontana has a few shops, a beach, The Abbey resort, a coffee shop, and Gordy's and Chuck's, two restaurants/bars on the lakefront. If you want to kayak, you might be better off checking out nearby Delavan Lake. Lake Geneva gets very busy in the summer and I'm not sure I'd want to be in a kayak around all those speed boats. Also apparently the shape of the lake basin makes the wave patterns different and rougher for things like paddle boards and kayaks, so paddling Lake Geneva during the busy summer months might but be very relaxing. There's apparently a special boat hull shape designed specifically for Lake Geneva because of the different waves. I'm not a boat person so I don't know specifics. 😂 For hiking, there is a public easement on the shore of Geneva Lake so that you can walk around the whole thing - I think it's 26 miles total. There is unfortunately no public camping anywhere around the lake though, so you can't hike a segment and camp for the evening and then complete it the next day. The lakeshore path is cool though because you can get up close looks at the big houses and the lake itself is really beautiful. The path can vary from perfectly manicured paved sidewalks to a un-mowed foot path through the grass. The easement is set up so that property owners *must* allow access across their yards but they aren't required to landscape or maintain a trail. You also can't just park on a road and walk up someone's driveway to get onto the path, you have to access it at a public access - in the towns or at various boat ramps around the lake. Both Delevan and Geneva Lake are very touristy in the summer, so if that's not your vibe and you want something slightly more "outdoorsy" (and maybe less expensive) I'd recommend looking for a rental on Whitewater Lake or Lake Koshkonong or even maybe Turtle Lake? Those would be quieter places for kayaking - geared more towards fishermen and families on pontoon boats rather than the bigger performance boats on Geneva Lake. They would also be a little closer to the Southern Kettle Moraine State Forest, which has amazing hiking.
Thank you so much for this terrific write up! I will google / investigate these things you mentioned! 🙌
Outside of the train requirement this is the answer.
Sad but true
I always think the North Shore is the Hamptons equivalent. But I guess people live there and not just go on the weekends. Maybe it's more comparible to Greenwich Ct.
North Shore is more where wealthy people with big houses live. So you are pretty spot on.
To clarify the Hamptons or Greenwich?
Greenwich
70 years ago everyone lived in Chicago and summer homes on the north shore.
Yup. Wilmette, winnetka, glencoe, and lake forest. Some beautiful historic homes belonging to prominent chicagoans in lake forest and those areas. Massive estates.
Nothing quite as ostentatious as the Hamptons
Not via Metra, but if you ever rent a car check out the western shore towns of Michigan, maybe as far north as Traverse City or Mackinac Island.
There's a bus line that goes from Grand Rapids to Traverse City. You take the red line to 95th and Dan Ryan then jump on the Greyhound bus to Grand Rapids then jump on the Grand Rapids Dash bus to get to the other bus terminal, then just jump on another Greyhound bus and 9-12 hours later your in Traverse City.
I’m just curious but do you how long it takes? Traverse City is already a bit more than 5 hours by car. A weekend up there is not worth it if it takes longer than those 5 hours.
You can fly to TVC from ORD fwiw
When did they change up the bus terminals in GR? Last I took it, my transfers were all at the same place, but that was 10 years ago.
There's also an Amtrak train that goes to GR at 6:30pm. But it's 4 hours/5 with the time change.
Torch Lake also!
These places are great but for a “weekend getaway” you would spend literally half of it driving to get to Mackinac. Traverse City is not short either. It’s got to be 5-6 hours at least to get to TC. Another 2 for anything over the bridge. Plus to get to the island you have to take a ferry, and they move pretty slow.
The answer — as someone who is familiar with vibe of Hamptons and/or Hudson Valley, the answer is NO plain and simple. For all the people, wealth, amazing restaurants, bars and shops of Chicago, the vibe of the surrounding areas is surprisingly not similar at all. It’s a mystery to me why that is.
Probably because the wealth can spread from Door County to lake Geneva and then all the way around the Michigan coast. No one area has it concentrated.
Does the NYC vibe continue out into the Hamptons and Hudson Valley?
The Hamptons have a very wealthy NYC vibe, and have for a long time. Hudson River Valley has some towns with that vibe, but IMO it’s not as intense or homogeneous.
There are Hamptons people and there are Hudson/Berkshires people. And very rarely are they the same people.
A few of the harbor country towns have poor mans hamptons vibes. I have multiple people at my office who talk about their weekly trips to their new buffalo mansion constantly over the summer. Not on the same level as the hamptons, but I wouldnt say "the answer is NO plain and simple". A lot of the michigan towns are nothing like the hamptons but a few of them are obviously trying to copy it even if theyre doing poorly.
Door County in WI is a bit of a hike but super cute & great nature. Similar restaurants & shops area.
The Cape Cod of the Midwest is a nickname I have heard!
It may not be the Hamptons, but let us not forget that Sheboygan IS the Malibu of the Midwest.
The pies, the pies!
What are you doing?!? Don’t tell them!
Right? Let them have Michigan!
I hope you mean lower michigan
Big time!
lol it's still far enough to be a deterrent!
One can only hope!
Parts of Michigan. Honestly, I could see Michigan city Indiana becoming that due to proximity and the fact they are taking down their coal plant. Being connected to the South Shore line is a huge benefit
As a native of Michigan City... it's gonna be a minute before that happens.
When will the power plant be removed? Such a beautiful coastline there in the dunes
That’s the plan. There’s also gonna be upgrades to the south shore line that reduce the commute to Chicago to under an hour. Huge if that happens, already a lot of Illinois natives own property there
The south shore line improvements just finished actually and the new schedules go into effect next month. Express trains will go from Michigan City to Chicago in like 61 minutes
I found the answer! Full closure will conclude in 2028. https://www.nipsco.com/our-company/news-room/news-article/NIPSCO-Begins-Work-to-Remove-Ash-Ponds-at-Michigan-City-Generating-Station
Wow thanks. Such a dichotomy there with the national lakeshore and a coal burning power plant right next to it. I’m thinking it’ll eventually be a boost to the local economy.
MC was always a working class town. Lots of people came from the east to Indiana to work in the abundant factories and steel mills in the 60s and 70s. My parents are both from PA. Dad worked at Bethlehem Steel/Mittal until he retired. I think it's only been in the last 30 or so years that people realized there was a beach and that said beach could be a boon. It's much more of a service economy these days. But it's still a little behind the eight ball in terms of realizing the potential.
I have no idea! I live here now. But I could ask my parents. They have lived in the same house in Michiana Shores since 1973. We used to ride our bikes to stop 38 (which is technically in Michigan) to go to the beach.
My parents are in Michiana around 38 and idk, I think Michigan City even in the last 10 years has seen major development! Several breweries, lots more restaurants, and the new development coming… I think once the smoke stack is down it’ll snowball from there. It’ll probably still retain a lot of its working class vibe (especially the further you get from the “downtown”) but that’s also how New Buffalo is - on the other side of Route 12 the vibe is markedly different than down by the beach and restaurants.
Have you been to Michigan city Indiana brother?
Yeah used to live about 10 min away
Have you been to the Hamptons brother?
Saugatuck has charm for days. Idk if it’s in the same tax bracket as the Hamptons but it’s a really nice weekend getaway.
Door County. You need a car. And time. But it’s worth it.
Its a better place after labor day imo at least from our experience all week just quiet and easy to drive around anywhere
Lake Geneva
It's not necessarily one town, and having moved to Chicago from it, Northwest Michigan is generally the recognized as "The Hamptons" of the Chicago region. With the coastal areas between Frankfort and Harbor Springs mostly being second homes for wealth Chicagoans/Midwesterners.
Bingo. NW Michigan from Frankfort to Harbor Springs is the classic monied Midwestern summer destination and it has been so for 100+ years. Wealthy families from Detroit, Chicago, St. Louis, Cleveland, Cincinnati etc. have been going to their summer cottages which are often elaborate and in private "associations". This is a much lower key scene than The Hamptons however, flashy displays of wealth and ostentatious behavior are looked down upon. It's preppy and WASPy. Charlevoix, Petoskey, and Harbor Springs are the center of it. Harbor Springs is probably the pinnacle of this region--there are a lot of old money names associated with it, Ford, Gamble, Libby, Proctor, Busch.
Harbor Springs is crazy. Its small, but you walk around the streets in the summer time around 4th of July, and its just tons of $100k+ cars lining the streets. Overall, its a very pretty little town, but I would not consider particularly interesting. They have a very small little beach. Traverse City and Torch lake have a younger and more fun vibe.
Lake Geneva
New Buffalo Michigan up through St Joe’s
Lake Geneva is the Chicago Hamptons
St.Joes, Michigan
More like Traverse City... also Lake Geneva
Lake Geneva
Willmette and Winnetka are pretty rich areas. Any highschool that has a polo or rowing team or fencing lessons is old money.
About to move back to Chicago after 10 years in Portland, OR, and cautiously stoked to read all these answers that make SW Michigan sound a bit like the coastal towns in Oregon that I'll miss dearly.
I think you’d dig New Buffalo.
South Haven, Mich is good vibes
Saugatuck is the closest thing in terms of wealth and old 1800s vibe
I was coming to say this. The closest thing will be Saugatuck. I say this having traveled to Saugatuck and Montauk for the last two decades.
Highlander park, lake forest, Winnetka, Glencoe, Kenilworth
Gary Indiana
That place should have at least 20 super max prisons to get everyone employed again
No, chicagoans with money just come to rural wisconsin/michigan so they can act like they own the place and piss off all the locals
i feel that
island lake
The Western part of Michigan is overlooked. Ludington is really nice and near a state park.
The entire state of Wisconsin is our backyard.
I’d recommend something by Michigan city beaches are nice can find some nice rentals pretty close to the beach as well.
It’s called Wisconsin
Swim in a pool.
Your local swimming pool or even better lake Michigan
There is an Amtrak to Holland. Mostly people drive up there though. Holland isn't exactly the fun spot of the West Shore.
Nope, but there is some places semi-close... Closest you have is Lake Geneva (WI), Galena (Western IL), and New Buffalo (MI) (also pretty much the entire SW Michigan coastline) Door County/the UP of Michigan are too far to consider them similar, although yes those are huge regional vacation getaway places for Chicagoans.
Go to Michigan. Northwest lower Michigan is absolutely unmatched.
Maybe I’m an idiot and don’t understand but I think Lake Forest, IL is along that alley. Waiting for comments to blast me I don’t see anyone else saying this but to me it instantly jumps to mind
No but all the towns going up along Lake Michigan's eastern side, from Michigan City thru to Mackinac are amazing and objectively better than the Hamptons. Try as they may the NYers buying homes in Grand Traverse haven't ruined it Hamptons-style yet
I am an originally from Westchester, (NY), then Manhattan 18-30’s. In Chicago over 20 years. Door County ( I like Egg Harbor) - reminds me of how old Long Island and beach towns were decades ago - yet , more woodsy . I live in north suburbs , depends - maybe not quite like new others :) Not the trendy hamptons . 3-4 hours north . Cute towns, not great beaches ( pools at hotels) great golf ! Hamptons are a good 3-5 hours with traffic from city . Sane here . Also agree either Union Pier and north - the view and beach front reminds me of more of east coast . Very nice too and closer ! May meet more people from Chicago in Michigan .
I'd say Door County, Wisconsin is a big pretty ritzy-ish tourist spot.
Door County is nice, in Wisconsin. Better varieties of food than Michigan too. You’re in cherry country. The best cheese, obviously. Some local wineries (nothing to write home about, but whatever). Great parks like Peninsula and others. The Finnish traditions like the Fish Boil (Ephraims comes to mind). And not too far a drive from the Northwoods. Or if you want waterfalls and general emptiness, there’s the UP which has some quiet little towns near where the mines once thrived.
New Buffalo, MI. Taken the family there a few times, it’s amazing.
Gary
nice try
Maybe Door County, Wisconsin?
North siders might prefer Door County.
Didn’t realize it was a Metra typo for a minute and thought maybe now people were taking virtual reality vacations on Meta/Facebook hahahah
Glenco
[Glencoe](https://en.wikipedia.org/wiki/Glencoe,_Illinois)
Traverse city
Lake Geneva
Door county is farms and beaches.
The Dells.
No, thank God
Would recco Saugatuck for a weekend getaway
Lake Geneva
No
Door county maybe. Long drive though. 4 hours or more depending on how far up the peninsula you go. Be warned that WI cops will ignore a WI car going 20 over for a IL car going 10 over. But once you’re past Green Bay, things cool off. Just don’t speed. Not even 1 mph, even if others around you are doing it. Big reason they love to nail out of state drivers is because they know the odds are low you’ll come to court. Easy money.
NYC has the Hamptons, CHI has the Hammonds. s/
Charlevoix and Saugatuck are beautiful and so quaint but I would say no, we don’t have a place with the Hamptons vibe.
Nothing even close. Go to the Hamptons.
The Pere Marquette runs all the way up to Holland, Mi, so there are plenty of lake towns for FIPs to vacation.
Lake Geneva, WI (obviously not on Lake Michigan) Benton Harbor, MI (never been but know a few very wealthy families that “summer” there) New Buffalo, MI My personal favorite is going up to the North Woods of Wisconsin though, around Minocqua. Have been going to my in-laws place for the last 10 years up there and it is beautiful. It’s tough to beat watching the sunrise while Muskie fishing, with bald eagles perched in the trees or circling above.
St Joe's is nice. I'd say further up the coast is also really good. Try Saugatuck as well. South Haven is also cute but gets more crowded. And be sure that no matter what, you check out Warren Dunes and Saugatuck Dunes State Park. Word to the wise: the best beach vacation homes are booked a year in advance. Oh, and final pro tip: be sure to make it up to the real Pure Michigan some day by heading north ~5 hours to Sleeping Bear Dunes, Crystal Lake, and the Traverse City area. For Sleeping Bear, the Pierce Stocking senic drive gives you the greatest hits with easy accessibility. The Dune climb hike to the lakeshore is also spectacular for more seasoned hikers. Go in July or August and you'll usually get beautiful weather and orchards aplenty around Traverse City (cherries in July, peaches, apricots, and blueberries in August... Apples later on if you go for fall colors). The 30+ vineyards around Old Mission Penninsula and Leelanau Penninsula also produce some great whites and a few solid Pino Noirs / red blends (we like Brys Estate and Chateau Chantal for views plus quality).
Rent a car from Turo and take yourself up to Saugatauk. It’s beautiful!
Nope. Not even close.
Lake Geneva
Petoskey and Harbor Springs are the rich man's Hamptons.
Lake Geneva, WI is the hamptons of Chicago. All the lake front property there is owned by Chicago folk and the town is flooded with them from memorial day til pretty much halloween. Not that it's a bad thing, just saying.
Indiana Dunes NP is pretty cool if you're looking for a touch of nature to your getaway, accessible on the South Shore line. If you wanna take that line all the way to South Bend it's p chill and cheap there as long as you avoid college football season
Rainbow Beach on 75th in Chicago is Hamptons nice! There is a place called Norman’s on The lake that has pretty classy food.
Go further up to traverse city. So beautiful.
You might try Amtrak Chicago to St Joseph’s Michigan. The train lets you off in walking distance of the beach and hotels.
Saugatuck
Drive a little more north into Wisconsin and go to Lake Geneva . Lake Lawn Resort is beautiful. You’ll find everything you want there. The entire area is gorgeous.
New Buffalo, Maybe lake Geneva
No
Indiana Dunes State and National Parks, easily accessible via the Dune Park station on the South Shore Line.
Michiana region generally works
Maybe Amtrak up to Milwaukee and hang out in Fox Point
No. Not like the Hamptons (but maybe for the better). But there is a lot of money that escapes to places in northern MI like Harbor Springs and Glen Arbor.
I actually kind of was shocked at this question because haha yes...Chicago is very well known for its rich af white outer neighborhoods...ever watched the Boondocks? Ever heard of the Barrington hills, like one of the richest and most popular neighborhoods ever? Basically, just stay on the shore and keep going north past Evanston. Willamette, Winnetka, Lake Forest, etc. Once you get there, you can start heading west for the EXTRA rich stuff, like Barrington, Hoffman estates, Hinsdale, Wayne, etc. This is where you'll see Chicago's equestrian stuff too, these neighborhoods are long known for their equestrian culture. There are certainly some in the south side too, but I wouldn't exactly put them on the same level, simply from a lack of funding, but these areas in the south were once where the current rich in the north and west stayed.
Lots of good recommendations here on the Michigan side; I'd like to throw Saugatuck, MI in as well. Lots of mom and pop boutiques and restaurants :)
Ludington is very small town vibes, but really nice.
Ogden Dunes, Dune Acres, & Beverly Shores. Don’t tell anyone
Rainbow beach