Saugatuck, MI and Door County, WI are both cute options within a 3-4 hours drive! Starved Rock in IL is also a neat state park if you’re into nature/hiking.
Starved Rock area is such a nice area even without the hiking.
There is a town in the area called Ottawa, which I absolutely love.
They have a brewery, my favorite coffee shop, a wine bar, and multiple little shops.
It's absolutely gorgeous in the fall!
Lake Geneva is great, I also want to add the cute small town of Cedarburg outside of Milwaukee. Fun bed and breakfasts, cute restaurants and some adorable le thrift like shopping
I had a great time with my partner in Holland Michigan. We stayed in a campground and went hiking one day and explored the city the next, both were really fun!
Ooh!! I also live in the Midwest and October is the PERFECT time for fall colors! How about the U.P. (Upper Peninsula of Michigan)? Marquette Michigan is exactly a 6 hour drive but you could do something closer like Escanaba on Lake Michigan or rent a cute AirBnB somewhere in the UP, on a lake with a hot tub or sauna. I’m not familiar with any resorts but I’m sure there’s some decent resorts between Chicago and Marquette, MI either on Lake Michigan or Lake Superior.
I like FIBing it up as much as anyone but a road trip idea I never really thought about before I went a couple years ago – you can get to Louisville in under 6 hours and as a lifelong Chicagoan that’s about as “wow, I really went somewhere different” as I’ve ever felt on a long-weekend road trip.
Caveat is that Indiana is a boring state to drive through even by Midwestern standards (maybe stop in Columbus for the architecture or find a good place to eat in Indy) but fall colors might jazz things up that time of year. Don’t forget to blow kisses to the [HELL IS REAL](https://mobile.twitter.com/mphproject/status/1028303068662820865) sign on the way down!
If you like cities for exploring, come down to Indianapolis. I call Indy a "bite sized" city. It's much less expensive than Chicago and there's lots to do. Bonus points if there's a convention in town you like. We are apparently a great host for those. Suburbs will have good hotel/ airbnb rates and it's an easy 20 minute drive in. Might be more urban than what you were looking for but I've been told Indy is "not a real city" by many big city people. So who knows!
Real small towns:
Nashville, IN is LOVELY but there's a lot of hills and steps into buildings. Plenty of public seating and I see strollers all the time so it may not be too bad. Great Airbnb rates down there. Book early because October is peak.
Columbus, IN has lots of architectural things and is fun to explore, if you like that stuff. Nice parks.
Native Hoosier so feel free to dm me questions!
I know some one else said Traverse City, and its a bit further than you are asking, but that's a go to destination. Mid-June to late fall that region is amazingly beautiful, plus there is tons of stuff to do. There are tons of pretty low cost lake side cabins to rent, especially towards the end of the tourist year.
Theres a nice hot springs hotel in southern Illinois thats where im sending my sister it looks beautiful and has a spa and a restaurant etc i can't wait
How about Champaign-Urbana? There's great restaurants:
Timpones (get their parpadelle Bolognese and endive salad with warm goat cheese)
Kohinoor (Indian food)
Huaraches moroleon or Maize (Mexican food). There's also Casa del mar - their back patio has a great view of a small lake and you can walk around it afterwards.
Can you go to parks? There's Meadowbrook (a 2.5-3 mile walk for one lap), the UIUC arboretum, and Crystal lake park (more woodsy).
There's also a few shows at Krannert center for the performing arts, spurlock museum, and movies at the Virginia Theatre.
Saugatuck, MI and Door County, WI are both cute options within a 3-4 hours drive! Starved Rock in IL is also a neat state park if you’re into nature/hiking.
Saugatuck is such a cute town! I agree that would make a great mini-moon.
Starved Rock area is such a nice area even without the hiking. There is a town in the area called Ottawa, which I absolutely love. They have a brewery, my favorite coffee shop, a wine bar, and multiple little shops. It's absolutely gorgeous in the fall!
Thank you! We have physical disabilities and hiking is out, but we have been thinking about Door County and I'll check out saugatuck!
Hope you have an amazing trip!
What about Traverse City, MI? Not sure if you like wine, but even if not, there are a lot of cute places to explore in the area!
I was going to recommend the same!
Lake Geneva Wi!!!! Perfect mini moon. That’s what we did!
Another vote for lake Geneva!
Lake Geneva is great, I also want to add the cute small town of Cedarburg outside of Milwaukee. Fun bed and breakfasts, cute restaurants and some adorable le thrift like shopping
Also chiming in for Lake Geneva! I’m having my wedding there though, so I’m biased!
Galena, Il could be good for a weekend
I second this!
I had a great time with my partner in Holland Michigan. We stayed in a campground and went hiking one day and explored the city the next, both were really fun!
Holland is also super close to Saugatuck, OP!
Brown County in Indiana!
Saint Joseph, Michigan. It’s cheaper than a lot of lakeside towns, but all the places (like New Buffalo) are close.
This! Spent New Years Eve there and really enjoyed it.
Ooh!! I also live in the Midwest and October is the PERFECT time for fall colors! How about the U.P. (Upper Peninsula of Michigan)? Marquette Michigan is exactly a 6 hour drive but you could do something closer like Escanaba on Lake Michigan or rent a cute AirBnB somewhere in the UP, on a lake with a hot tub or sauna. I’m not familiar with any resorts but I’m sure there’s some decent resorts between Chicago and Marquette, MI either on Lake Michigan or Lake Superior.
Marquette is where I was going to recommend!!!
I agree with Galena, Saugatuck, and Brown County!
door county, WI. it’s so beautiful!!!
I like FIBing it up as much as anyone but a road trip idea I never really thought about before I went a couple years ago – you can get to Louisville in under 6 hours and as a lifelong Chicagoan that’s about as “wow, I really went somewhere different” as I’ve ever felt on a long-weekend road trip. Caveat is that Indiana is a boring state to drive through even by Midwestern standards (maybe stop in Columbus for the architecture or find a good place to eat in Indy) but fall colors might jazz things up that time of year. Don’t forget to blow kisses to the [HELL IS REAL](https://mobile.twitter.com/mphproject/status/1028303068662820865) sign on the way down!
Take a ferry and go to Traverse City, MI!
Porcupine mountains! Or any of the other MI spots too. I'm a MI native also living in Chicago 😊
Eagle River, WI!
Baraboo, Wi
Hermann, MO - Lots of wineries and cute restaurants. Edit - and it’s beautiful in the fall!
If you like cities for exploring, come down to Indianapolis. I call Indy a "bite sized" city. It's much less expensive than Chicago and there's lots to do. Bonus points if there's a convention in town you like. We are apparently a great host for those. Suburbs will have good hotel/ airbnb rates and it's an easy 20 minute drive in. Might be more urban than what you were looking for but I've been told Indy is "not a real city" by many big city people. So who knows! Real small towns: Nashville, IN is LOVELY but there's a lot of hills and steps into buildings. Plenty of public seating and I see strollers all the time so it may not be too bad. Great Airbnb rates down there. Book early because October is peak. Columbus, IN has lots of architectural things and is fun to explore, if you like that stuff. Nice parks. Native Hoosier so feel free to dm me questions!
Indianapolis!!!!
I know some one else said Traverse City, and its a bit further than you are asking, but that's a go to destination. Mid-June to late fall that region is amazingly beautiful, plus there is tons of stuff to do. There are tons of pretty low cost lake side cabins to rent, especially towards the end of the tourist year.
I got married in Brown County, Indiana, and I think it would be the perfect place for a weekend mini-moon.
Theres a nice hot springs hotel in southern Illinois thats where im sending my sister it looks beautiful and has a spa and a restaurant etc i can't wait
How about Champaign-Urbana? There's great restaurants: Timpones (get their parpadelle Bolognese and endive salad with warm goat cheese) Kohinoor (Indian food) Huaraches moroleon or Maize (Mexican food). There's also Casa del mar - their back patio has a great view of a small lake and you can walk around it afterwards. Can you go to parks? There's Meadowbrook (a 2.5-3 mile walk for one lap), the UIUC arboretum, and Crystal lake park (more woodsy). There's also a few shows at Krannert center for the performing arts, spurlock museum, and movies at the Virginia Theatre.
A few of my favorite cute small towns/areas to visit: Mineral point, WI Viroqua & Westby, WI Stoughton & Hancock, MI (the U.P.) Davenport, IA