The Best Weekend Trips From Chicago

Okay guys, I’ve finally given in to Fall in Chicago. I am no longer fighting the crisp breeze or changing leaves. We are officially in the best part of Fall, and I am here for it. There’s just something magical about Fall in the Midwest, isn’t there? And this is why today’s Friday Roundup is all about the Best Weekend Trips from Chicago.

If you aren’t from Chicago, don’t worry! These places are still so fun to visit, no matter where you live. But for my city gals – a weekend trip is always more likely to actually happen when you can just hop in the car and GO, right? Exactly ?

Also, before we dive in, I just want to mention that my pink sweater is only $23 right now. It’s super soft and runs true to size and I own it in 2 colors! Highly recommend!

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 last winter and LOVED it. As for Fall, you can go apple picking, visit a pumpkin patch, or just admire the changing leaves along the lake!

Grand Rapids, Michigan

Adam and I went to Grand Rapids last September and had the best time. This city may be small, but it has a lot going on. We especially loved Robinette’s Apple Haus & Winery and the incredible food scene. You can read about everything we did on our trip in this post!

Madison, Wisconsin (pictured above)

I just had the pleasure of going to Madison a few weeks ago, and now I understand why so many people from my High School went to college there! I have a whole blog post about my visit coming next week, but in the meantime, be sure to check out The Lucille for dinner (get the Umami Pizza!) and set up some time to craft 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, South Haven and Saugatuck, Michigan

I’ve only ever been to South Haven, but I’m including all 4 here because a few ladies in my LSL Community Group on Facebook said you can do all of them in one long weekend! 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. Could be a fun little Michigan road trip – plus it could be fun to see how many pumpkin patches you can find! ?Also, if you go to South Haven before the end of October, you MUST go to their Farmer’s Market. We had the best tamales there when I went for my sister-in-law’s bachelorette party. Mmmm!

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, plus they have their Annual Fall Fest this weekend! Get in the car, what are you waiting for?!

Louisville, Kentucky

When I asked for suggestions in my Facebook group, I was surprised that so many people suggested Louisville! I always thought it was so far away, but it’s only 4.5 hours from Chicago, which is totally doable for a long weekend. Most people said that the Kentucky Bourbon Trail is an awesome experience. Plus my friend Shaheen just moved down there, so now I really want to go!

Milwaukee, Wisconsin

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!

Shawnee, Illinois

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 ?

Kohler, Wisconsin

Every person I know who has been to Kohler has raved about it. Not only do they have a five-star resort, but the Kohler Waters Spa is one of only 60 five-star spas in the whole WORLD. They also have Yoga on the Lake, which I’m assuming is awesome because I just took class with one of their instructors and two of my favorite teachers from CorePower Yoga work up there, too!

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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!!

PS. You might also like 10 Things To Do In Grand Rapids and Our Cozy Winter Weekend at the Grand Geneva.