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Day Trips From Chicago: 10 of the Best Places to Visit

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Day Trips From Chicago, by Travel Blogger What The Fab

Planning a trip to the midwest? You’ll get plenty of inspo from today’s post, with a round-up of the best day trips from Chicago!

I love Chicago. It’s one of the coolest cities in the country, and I love spending time there.

Despite how much there is to see and do in the Windy City, I’ve also discovered that there are loads of day trips from Chicago that are totally worth leaving all the big city attractions for. From small-town, cultural gems to incredible experiences with nature, there’s a whole lot waiting for you within just a couple of hours of the city.

Pssst, heading to Chicago? Don’t miss these travel guides to help you plan your trip!

Chicago Travel Guide
Where to Stay in Chicago
Chicago 3 Day Itinerary
Gwen Hotel, Chicago

So if you’re looking for perfect one-day or weekend getaways, I’ve rounded up these 10 day trips from Chicago you need to check out!

10 Day Trips From Chicago

1. Lake Geneva, Wisconsin

Chicago, Illinois already sits on one of the largest lakes in the country, Lake Michigan, so you might be thinking that driving over one-and-a-half hours away from Chicago to go to another lake in Wisconsin seems nonsensical.

The reason is that the Lake Geneva experience is totally different from anything you’ll find in Chicago.

As a well-known Wisconsin resort city, Lake Geneva is where Chicago’s high rollers used to go to rub elbows. It’s where the rich from the big city came to set up their Gatsby-esque mansions during the Gilded Age and has kept its reputation as a high-end holiday destination ever since–and rightfully so because this place is gorgeous!

One of Lake Geneva’s main highlights is the 21-mile Lake Geneva Shore Path where Visitors can stroll or bike along the shoreline to take in the sights of these former grand estates and sporadic art installations. For an on-the-water view, taking a boat cruise is another super cool option. 

You’ll also find plenty of awesome restaurants, nightlife, boutique shops, and a variety of other outdoor activity options to keep you entertained for an extended day trip or a weekend getaway. It’s one of the best day trips from Chicago!

2. Oak Park, Illinois

For a charming piece of suburban Americana, you can’t do much better than Oak Park. Even though it shares a border with Chicago on the west side, stepping into Oak Park is like slamming on the brakes and bringing life down to a much slower, relaxed pace—it definitely has that small-town charm.

Not only will you enjoy the quaint neighborhood feel as you stroll along its small-town streets and browse the boutique shops, but you’ll get an up-close look at what true Prairie School architecture looks like. This is mostly due to the influence of Oak Park native, Frank Lloyd Wright, whose studio and adjacent home welcome visitors from near and far all year round.

The 60-minute tour of the Frank Lloyd Wright home and studio is really interesting and well worth the time.

A handful of other local historical museums, classic architecture, and vibrant Arts District also warrant the popular self-guided tour of the neighborhood that you can complete on foot or bike.

No matter how you decide to explore this town, you’re bound to fall in love with it.

Day Trips From Chicago, by Travel Blogger What The Fab

3. Milwaukee, Wisconsin

The first thing that may come to mind at the mention of Milwaukee is beer. And that’s not far off, as this Wisconsin city’s beer heritage runs deep. If you’re a beer lover, you’ll have a blast exploring the vast abundance of local craft beers, microbreweries, and a handful of historic brewery tour options.

But there’s a lot more to Milwaukee than its beer culture.

Just an hour and a half away from Chicago, you’ll find yourself in yet another vibrant metropolis full of history, art, and a thriving foodie scene.

For the best local food and shopping experience, make your way to the Milwaukee Public Market in the middle of the city’s Third Ward historic neighborhood. Here you’ll find rows of independently-owned vendors selling their unique delicacies and goods that you can get lost in and spend hours exploring.

If you want an authentic taste of Milwaukee, this is where you’ll find it! You can also quickly shift gears into ultra-relax mode by escaping to the peaceful, natural setting of Lakeshore State Park in the heart of the city.

Here you’ll find 22 acres of Lake Michigan lakefront bike paths, walking trails, and fishing areas, plus a number of other outdoor activities going on like kayaking and canoeing. As you can see, Milwaukee’s got it all!

Day Trips From Chicago, by Travel Blogger What The Fab

4. Holland, Michigan

Nope, no international passport is needed for this venture! The Holland I’m talking about isn’t in Europe–it’s a Michigan city in the US, about a two-and-a-half-hour drive from Chicago.

Just as you’d expect from its name, Holland in Michigan radiates Dutch heritage. The biggest testament to this is the 4.5+ million tulips that bloom throughout the city every spring. 

If you can make it to Holland in early May, you’ll be lucky enough to join the crowds of visitors that flock to the city for the Tulip Time Festival to partake in celebrations involving Dutch food, parades, music, and to give it a go at traditional Dutch folk dancing.

Aside from the sea of tulips, you’ll also be enchanted by Holland’s old-fashioned windmills, picturesque gardens, and European-style villages. Taking a stroll through the iconic Veldheer Tulip Gardens and Windmill Island Gardens is a treat any time of year.

You won’t want to miss Holland’s other charms like their old-school-style cafes, restaurants, and bakeries that whip up all sorts of Dutch delicacies.

The best way to enjoy Holland is just to meander through this beautiful town and let yourself take it all in! If you have some free time while you’re exploring Michigan, be sure to make a pit stop to see the Grand Rapids.

5. Kettle Moraine State Forest

Hop in the car and head north towards Wisconsin, and in less than two hours, you can reach the spectacular Kettle Moraine State Forest that sits just north of the Illinois/Wisconsin border. Here you’ll find over 22,000 acres of glacial hills covered by lush forest, prairies, and lakes.

Besides having some of the most scenic trails you’ve ever seen, there isn’t any type of outdoor activity that you can’t do at Kettle Moraine.

Want to go hiking, mountain biking, or horseback riding? You can do that.

How about fishing, paddling, swimming, boating, or hunting? Yep, you can do that here too. 

Setting up camp for a night (or several) isn’t a problem either. There are two group camps, three family campgrounds, a camp for horseriders, and–for the hard-core nature lovers–even some isolated backpack shelters out on the Ice Age Trail.

Kettle Moraine is great because it has trails for every level of hiker that range from very easy to intense. The landscape changes from season to season, and you’ll find varying types of flora and fauna depending on what time of year you go.

The majestic trees are an exceptional sight to behold in the fall! 

Day Trips From Chicago, by Travel Blogger What The Fab

6. Anderson Japanese Gardens

Recognized as one of the best Japanese gardens in North America, a trip to the Anderson Japanese Gardens is a sure way to revitalize the soul. This zen oasis is about an hour-and-half drive from Chicago in Rockford, Illinois.

If getting lost in a world with a Garden of Reflection, Pond Strolling Garden, waterfalls, bridges, pagodas, and immaculate koi ponds doesn’t instantly relax you, I’m not sure what will!

It’s all about wellness in nature at the Anderson Japanese Gardens, and everything about their perfectly manicured 12-acre grounds proves it.

One of the best parts about the gardens is all of the wellness programs and events they have available year-round. There are classes for Tai Chi, yoga, pilates, meditation, mindful art, and special “Awareness Walks in the Gardens” booklet that guides you through 10 stops in the gardens for a truly sensory, mindful experience. 

Day Trips From Chicago, by Travel Blogger What The Fab

7. Indiana Dunes National Park

If you’re looking for some serious outdoor activities combined with a beach day getaway, then Indiana Dunes National Lakeshore is what you need! Less than 50 miles away from Chicago, Indiana Dunes gives you 15 miles of beach along the southern shore of Lake Michigan.

Not only does this stretch of shoreline allow for some awesome beachcombing, but you’ll also find 50 miles of trails through the national park’s incredible landscape for walking or hiking. There are wetlands, forests, and prairies to explore on foot, bike, horseback, or snowshoe!

Indiana Dunes is an ideal family-friendly (and dog-friendly) destination. There’s a Nature Play Zone for kids and walking tours led by knowledgeable rangers that are fun for everyone.

To really get the most out of this amazing place, make your way up West Beach’s Succession Trail to get an unbeatable view of the legendary Chicago skyline.

8. Apple River Canyon State Park

Tucked in the northwest corner of Illinois near the Wisconsin border lies a lovely little spot where nature-loving Chicagoans can get away from it all. Apple River Canyon State Park is about a two-and-a-half-hour drive, so it’s best suited for those who want to make a weekend getaway or mini camping vacation out of it.

Apple River State Park is especially popular among hiking and fishing enthusiasts, as the river is primed for trout, sunfish, and small-mouth bass fishing.

There’s also a camping ground with scenic river-view picnic areas, outdoor grills, and more to make for a complete outdoorsy vacay. 

9. Starved Rock State Park

Waterfalls, canyons, and trails, oh my!

By traveling less than 100 miles from bustling Chicago, you’ll reach a completely different world in Starved Rock State Park.

It’s best known for its 15+ majestic sandstone canyons that have been formed over time by glacial meltwater. As such, many have amazing waterfalls that you can reach via a network of hiking trails. 

Starved Rock is in a league of its own when it comes to breathtaking scenery along the Illinois River and offering such a wide variety of outdoor activities that include rafting, horseback riding, boating, hiking, birdwatching, and more. 

Because it’s such an accessible destination in the great outdoors for Chicagoans and other surrounding cities, it’s a very popular place!

Chances are that you’ll be sharing the hiking trails with many other visitors–especially during holiday time or during the weekends–so plan accordingly.

No matter what, you’ll put those walking shoes to good use!

10. Matthiessen State Park, Illinois 

If you like the idea of taking a break from Chicago city life for a nature-filled escape full of hiking trails and amazing scenery–and are looking for a less-crowded option to Starved Rock–then Matthiessen State Park is your solution.

It’s located less than three miles from Starved Rock, so it’s super easy once you’ve made the one-and-a-half drive from Chi-Town.

Matthiessen is best known for its unique rock formations, lots of walking and stairs to reach the canyon below, and for getting wet! Waterproof shoes are a good idea because there’s water everywhere from the streams, creeks, and waterfalls that make the rocks slippery and the trails wet. 

Speaking of waterfalls, waterfall chasing is for sure one of the highlights of visiting Matthiessen State Park, especially in the spring. There are several falls to explore, including an impressive 45-foot cascade that separates the lower and upper dells.

Feel free to pack some food and enjoy a scenic lunch in the Dells Area of the park. You’ll find plenty of picnic tables, toilet facilities, and water fountains–basically, everything you need for a perfect break (or an entire afternoon) of total relaxation. 

That’s it, friends—my list of day trips from Chicago Illinois. I personally can’t wait for my next trip to Chi-Town and will definitely be planning some day trips of my own very soon.

Cheers to new adventures and enjoy your Chicago day trips. Be sure to tag me on Insta @wtfab if you decide to explore outside of the windy city.

Psst, planning a trip to Chicago? Make sure to Pin this day trips from Chicago post for later!

Traveling to Chicago? Explore my other Chicago travel guides here.

Chicago Travel Guide
Where to Stay in Chicago
Gwen Hotel, Chicago
Chicago 3 Day Itinerary
Famous Chicago Food You Have To Try
Top 11 Chicago Black-Owned Restaurants
22 Best Indoor Activities Chicago Has to Offer
20 Fun Things to Do in Chicago at Night
18 Most Instagrammable Places in Chicago


How many days do you need in Chicago?

It’s best to spend around 3 to 4 days in Chicago to really explore everything the city has to offer.

What is the best time of year to visit Illinois?

The best time of year to visit Illinois is in the springtime when the weather will be at its best and the city will be less crowded.

What is Chicago best known for?

Chicago is best known for:
– Skydeck Chicago
– Chicago Riverwalk
– Cloudgate (the Bean)

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