10 Best Day Trips from Chicago

Last Updated on September 28, 2023 by Nikki Jain

Chicago is a busy, bustling city that sees over 50 million visitors a year. The city is full of exciting things to see and do, but don't forget the fun day trips from Chicago too. From vineyards to parks, charming lakefronts to historic towns, there is something for everyone within 3 hours of the windy city.

Below are the 10 best day trips from Chicago.

Accomodation: 10 Best Family Friendly Hotels in Chicago

Best Day Trips from Chicago

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1: Holland, MI

Holland, MI
Dreamstime/Craig Sterken

Rich in Dutch heritage, Holland is the perfect day trip from Chicago. Visit during spring to see the 4+ million tulips in bloom at the Veldheer Tulip Gardens and Windmill Island Gardens. You can also visit the windmills and tour the DeKlomp Wooden Shoe & Delft Factory as well as the Holland Museum.

The area is known for its enormous sandy beach, the Holland State Park Beach. This is perfect in the summer months, when you are looking to relax, sunbath and maybe even try some surfing. If you are spending a weekend here, there are two large campgrounds with fire pits, picnic tables, and grills, so you can escape from the city for the weekend without spending too much.

Visit in May for the Dutch festival, which includes food, music, Klompden dancing, parades, or head here in late November for the Dutch Winterfest celebrations.

Holland is 2.5 hours from Chicago

Address: Holland, MI

2: Milwaukee, WI

Milwaukee, WI
Dreamstime/Larry Jordan

Jump on the Amtrak and head out to Milwaukee to explore a smaller but interesting American city. There are microbreweries, tours, and brewpubs all over the city, perfect for those looking for a local craft beer. Visit the Public Market for tasty treats or explore the decor shops around the Historic Third Ward.

Fancy some seafood? Head to St. Paul Fish Company after spending an afternoon strolling around Lakeshore State Park. If you have a little more time on your hand, take a tour of the Harley-Davidson Museum, which showcases motorcycle artifacts from the famous brand.

Time your trip to visit during one of the city's many festivals; Summerfest is a popular music festival and the world's biggest. Alternately, visit in June to catch the Milwaukee Highland Games, full of traditional Scottish food, highland dance, and all things Scottish or see the music, dance, and historic exhibits at Polish Fest. July and August also see many internationally-themed festivals, including Irish Fest, Dragon Boat Festival, Bastille Days, and Festa Italiana.

Milwaukee is 1 hour and 35 minutes from Chicago

Address: Milwaukee, WI

3: Michigan Wine Country

Michigan Wine Country
Dreamstime/Bruce Jenkins

In South West Michigan, you can find over 20 different wineries, ideal for anyone looking for a romantic or fun day trip from the windy city. Enjoy the fresh air, learn about the different species of grape, and enjoy some wine tasting. Most wineries are based in the Lower Peninsula, along Lake Michigan, with the lake effect climate protecting the vines in the winter and creating the ideal soil for growing grapes.

Popular wineries to visit include Black Star Farms Winery & Spirits, Chateau Chantal Winery and Brys Estate Vineyard.

Most vineyards are around 2 hours from Chicago

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4: Lake Geneva, WI

Lake Geneva, WI
Dreamstime/Christina Preiser

This beautiful lake is one of the most popular destinations for vacations and on many USA bucket lists. Apart from gorgeous views, you can also enjoy a hot air balloon ride above the lake or take a booze cruise with your friends. The area is packed with fantastic food, so try the restaurants while you are in town. Visit old-fashioned restaurants such as Anthony's Steak House or Baker House; the latter can be found in a 129-year-old Victorian mansion. Alternatively, try some home-cooked food at Corleone Sicilian Restaurant or the Next Door Pub & Pizzeria.

Those looking for something a bit different can try zip-lining or head to a magic show. The gorgeous historic mansions and estates are perfect for couples, while families may enjoy visiting the Geneva Lake Museum.

Escape the crowds downtown by walking the Lake Shore Path or visiting the quieter Lake Como. If you are looking to stay for the weekend, you can relax in the nearby lakeside towns such as Fontana and Williams Bay.

You can drive here, but the train from Chicago Union Station to Fox Lake then from Fox Lake to Lake Geneva takes 2 hours.

Lake Geneva is 1.5 hours from Chicago

Address: Lake Geneva, WI

Also Read: 25 Most Beautiful Lakes in the US

5: Starved Rock State Park, IL

Starved Rock State Park, IL

Located in the town of Ottawa, Starved Rock State Park is known for its canyon waterfalls and tall cliffs. Perfect for hiking and even camping, if you want a weekend, this state park offers 13 miles of rails around 18 glacier-carved canyons.

There is no entrance fee at this state park but note the campground gates open from 8.30 am to 10 pm each day. If you intend to follow the trail to see one or two trails, allow at least 2 hours for your visit.

Visiting on the weekend? To escape the weekend crowds, head to Buffalo Rock State Park for a quieter experience.

The state park is 2 hours from Chicago

Address: 2678 E 875th Rd, Oglesby, IL 61348

6: Saugatuck, MI

Saugatuck, MI
Dreamstime/Amy Kamps

With the stunning Oval Beach and various water activities to enjoy, Saugatuck is a popular summer day trip for many. Rent a kayak or paddleboat, sail along the waters, or enjoy the sand dunes at this luxury retreat scene.

The area is also known as the 'art coast of Michigan,' offering dozens of art galleries in the nearby towns of Fennville and Douglas. Hikers should head to the Saugatuck Dunes State Park while families may enjoy a visit to Wicks Park. If you have extra time, make sure to spend a night or two in the charming downtown area; this is full of cafes, unique boutiques, fabulous restaurants, and beautiful gardens.

Saugatuck is just over 2 hours from Chicago

Address: Saugatuck, MI

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7: Madison, WI

Madison, WI
Dreamstime/Sean Pavone

Another charming destination near Chicago is the city of Madison. Take a tour of the Wisconsin State Capitol building to learn more about the USA political system or explore the stunning Olbrich Botanical Gardens. While in the city, make sure you try the cheese and beer that the city is known for and rent a bike from one of the BCycle stations to explore. In the evening, head to the Terrace at Memorial Union, a chilled-out lakefront seating area with beer, amazing food and live music.

Best of all, the city is surrounded by lakes, with Lake Monona and Lake Mendota ideal places to enjoy a weekend away. Visit the public beaches or paddleboard your way around the lakes. Feeling zen? Try a yoga class on the water itself, testing your balance while strengthening your muscles during the paddleboard yoga lessons. Water lovers can try some scuba diving here too, as well as take a free sailing lesson with the Hoofers Sailing Club. Want to stay dry? There is plenty of cruise and pontoon boat rides on offer too.

Madison is a 2.5-hour drive from Chicago

Address: Madison, WI

Also Read: Madison, Wisconsin Top 10 Attractions

8: Six Flags Great America

Six Flags Great America

For those that love a theme park, Six Flags is a popular choice and makes for the perfect day out from Chicago. Open from April through to November, expect thrill rides, roller coasters and 40 rides designed for families and children too.

Tickets cost $79.99, but discounts can be found on their website when you book in advance. You catch the Up-N train, which takes around 2 hours, 20 minutes, or drive in less than an hour.

If you have extra time, make sure you check out Hurricane Harbor. This is a massive 20-acre water park full of water slides, river floats, children's water play zones, and even a surf simulator.

Six Flags is 1 hour from Chicago

Address: 1 Great America Parkway, Gurnee, IL 60031

9: Chicago Botanic Garden, IL

Chicago Botanic Garden, IL

Don’t want to go too far from the city? Head just half an hour away from Chicago to visit the colorful, majestic botanic garden. With well-manicured heritage gardens, gorgeous plans and self-guided tours, everyone can enjoy a few hours here.

There is also a Nature Play Garden and Growing Garden for those visiting with families as well as an onsite restaurant and birding classes. The garden is open from 8am to 5pm and is open every day of the year. Admission is free, but parking starts at $25 for non-members.

The gardens are 35 minutes from Chicago

Address: 1000 Lake Cook Rd, Glencoe, IL 60022

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10: Springfield, IL

Springfield, IL
Dreamstime/Paul Brady

A popular stop along Route 66, Springfield is 3 hours away but makes for a great long day trip from Chicago or a weekend away. The city is home to the Old State Capitol State Historic Site, dedicated to Abraham Lincoln. The home of the famous president also includes the Abraham Lincoln Presidential Library and Museum and the Lincoln Home National Historic Site. You can also visit the stylist Dana-Thomas House or take a stroll around the Washington Park Botanical Garden.

Springfield is 3 hours away from Chicago

Address: Springfield, IL

Also Read: Top 10 Tourist Attractions in Springfield, Illinois

Final Thoughts:

There are many things to do in Chicago but if you have some extra time, try to plan at least one day out of the city to explore the beautiful towns, cities, and parks nearby. 

It is possible to catch the Amtrak to some of these destinations, but the easiest and often quickest way to get around is by renting a car and driving. It is recommended that you compare car rental prices online and reserve your car in advance to get better deals.

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