The Best Weekend Trips From Chicago

Looking for a quick getaway that doesn’t require a plan ticket? Here are the Best Weekend Trips from Chicago!

There’s something magical about Fall in the Midwest, isn’t there? The crisp breeze and changing leaves – it’s pretty hard to resist. And while I always say that this is one of the best times of the year to enjoy the city, COVID has definitely shifted the energy here. So, as long as you can stay socially distant, you throw on some plaid, enjoy some apple picking, and indulge in pumpkin flavored everything for a few days.

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 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. 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!

Madison, Wisconsin 

I just had the pleasure of going to Madison last year, 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, 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, and I hear their Annual Fall Fest is a blast!

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 lives 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! Definitely considering doing a little mini-moon here after the wedding… stay tuned!

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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.