Looking for a quick getaway that doesn’t require a plan ticket? Here are the Best Weekend Trips from Chicago!
I am definitely a city girl at heart, but sometimes it’s nice to get away from the hustle and bustle of it all for a weekend away. Luckily, there are a ton of really great places that are just a few hours away!
While this post is called The Best Weekend Trips From Chicago, you don’t have to be from Chicago to enjoy these destinations! That being said, aren’t last-minute trips always way more likely to happen when you can just hop in the car and GO? So, let’s go!
The Best Weekend Trips From Chicago
Lake Geneva, Wisconsin
Like most people in Illinois, I’m most familiar with Lake Geneva. It’s only an 1.5 to 2 hour drive from the city, and it’s oh so charming. Summer is my favorite time to be there, but we also went a few years ago during the winter and LOVED it.
We went to Saugatuck at the end of last summer and were completely charmed. It is the sweetest waterfront town about a 3 hour drive away. There’s great food, great wine/beer/cider, great people, great everything! It’s become the weekend trips from Chicago that we talk about the most because we can’t wait to go back. You can read all about our entire trip in this post!
We went to Kohler for our mini-moon after our wedding!!! We stayed at The American Club where you can wear your robe from your room down to the Kohler Waters Spa. Also known as one of only 60 five-star spas in the whole WORLD. Talk about BLISS!
Grand Rapids, Michigan
Adam and I went to Grand Rapids a few years ago and we still talk about it. It’s definitely a small city, but it has a lot going on. If you go in the Fall, you must go to Robinette’s Apple Haus & Winery (pictured above) – it’s the cutest little apple orchard with tons of Midwest charm. We also loved Downtown Market, and Donkey Taqueria – you can read about our entire trip in this post!
I just had the pleasure of going to Madison for a work trip, and now I understand why so many people from my High School went to college there! Even though I followed I set itinerary, I absolutely looooved The Lucille for dinner (get the Umami Pizza!) and our little craft session at Revel. SO fun!
Plus, on your drive up, you could stop in New Glarus for a brewery tour! They also have rolling hills with walking trails and adorable buildings that look like a little mini Switzerland town was plopped in the middle of Wisconsin!
New Buffalo, St. Joseph, and South Haven, Michigan
I’ve only ever been to South Haven out of these 3, but I’m including them all because they came highly recommended! New Buffalo is about an hour and 15 minutes outside of the city and St Joseph is 15 minutes past that.
If you want to go further, South Haven is a 2 hour drive from Chicago – and Saugatuck is just 20 minutes past that! You could even do a fun little Michigan road trip!
Door County, Wisconsin
If I’m going to Wisconsin, Lake Geneva has always won because it’s so much closer to Door County. That being said, Fall is the perfect time to make the trek up there. Hiking the Peninsula State Park will be extra pretty with all of the fall colors, and I hear their Annual Fall Fest is a blast!
I always thought Louisville was so far away, but it’s only 4.5 hours from Chicago, which is totally doable for a long weekend. We’ve only been for a quick wedding weekend but a lot of people said that the Kentucky Bourbon Trail is an awesome experience. My friend Shaheen lives there and has more recommendations!
I’ve actually never been to Milwaukee, but I hear so many awesome things about it! You guys suggested checking out all of the breweries and the Milwaukee Public Market!
It never really occurred to me to explore southern Illinois – until now! A few followers mentioned the Shawnee National Forest, and after googling it, I honestly can’t believe that exists in Illinois! While you’re there, make sure you check out the Garden of the Gods. And maybe hit up the wine trail when you’re doing hiking 😉
What’s your favorite Midwest weekend destination?
I know there are a lot more options out there. So, if I left your favorite off this list, please comment below!!