10 Best Weekend Trips From Chicago For A Fabulous Getaway

This article has affiliate links to products which we may make commission from at no extra cost to you.

Treat yourselves at one of these charming and relaxing weekend trips from Chicago.

Chicago is a wonderful city filled with a bustling center, modern art displays, cultural spots, incredible skyscrapers and ample amount of greenness. This city is full of fun events, experiences and activities. If you have explored the city enough and are looking beyond it, there is a wide variety of destinations that you could plan a getaway to. Check out these amazing places that are reachable within few hours and are definitely all worthy for epic weekend trips from Chicago.

Best Weekend Trips From Chicago

1. Starved Rock State Park, Illinois

Starved Rock State Park, Illinois - Weekend Trips From Chicago
Starved Rock State Park, Illinois – Weekend Trips From Chicago

Starved Rock State Park is located just an hour and a half from downtown Chicago and yet, you feel like you are in another country! This state park is famous for its sandstone canyons, waterfalls, and river. It is one of the prettiest places in the state and is beautiful in any season. The Spring and Summer are probably the best to visit because of the lush vegetation and higher levels of water in the waterfalls. There are 13 miles of nature trails to hike and explore.

Highlights of the park include the Lover’s Leap Overlook, St. Louis Canyon with a waterfall and the Wildcat Canyon with a waterfall. The park is open sunrise to sunset but the visitor center is only open 9 AM to 12 PM Monday through Friday.

Whether you are on an adventure with your friends or family, Starved Rock is a must-see in Illinois! 

Where To Stay : There are 2 Resorts close by to enjoy for the weekend including one inside the park, Starved Rock Lodge. The second one is Grand Bear Resort which is a rustic 3-star resort just 2 miles from Starved Rock with an Indoor Water Park.

By Jennifer Of Family Trip Guides

2. Lake Geneva, Wisconsin

Lake Geneva - Weekend Trips From Chicago
Lake Geneva – Weekend Trips From Chicago

Lake Geneva, Wisconsin is the perfect weekend trip from Chicago. A quick one-and-a-half-hour drive will get you exactly where you want to be—a picturesque lakefront escape.

As the #1 Small Town for Adventure in USA’s 2019 Readers Choice Awards, adventure seekers will fall in love with everything Lake Geneva has to offer. Some adventurous activities in Lake Geneva include ziplining, hot air balloon rides, water recreation, and a safari park! If you are up to it, venture further out to the Wisconsin waterfalls to explore more of the state’s natural beauty.

Head over to Black Point Estate and Gardens to explore the magnificent summer estate constructed by Chicago’s Conrad Seipp in 1888. This beautiful estate was built originally as Seipp’s family getaway from the hustle and bustle in Chicago but has since transformed into a peaceful escape for wandering visitors to Lake Geneva.

The most popular time of year to visit Lake Geneva is during the summer, however, the city’s awe-inspiring beauty is just as beautiful in the spring and fall.

Where To Stay : Book a stay at The Cove of Lake Geneva which is nestled on the stunning shoreline of Geneva lake and in the heart of the town.

By Ellie Of Ellie’s Travel Tips

3. Milwaukee, Wisconsin

Milwaukee - Weekend Trips From Chicago
Milwaukee – Weekend Trips From Chicago

Milwaukee is a must-visit city in the US that is situated only 100 miles from Chicago. Visiting a little north from the largest city of Wisconsin is worth it. Milwaukee sits on the banks of Lake Michigan and every corner of the city is picturesque. Reaching Milwaukee from Chicago is easily accessible by train or car. It just takes one and a half hours to reach there. After visiting there, you will see that most bike lanes are surrounded by the scenic waterfront. Moreover, the city is popular for craft beer as it produces beer on a large scale. There’s a lot more the city has to offer.

When you enter the beautiful city, start with visiting the breath-taking Milwaukee Art Museum. Continue roaming around the city by exploring the Milwaukee Public Market.

Attending a Green Bay Packers Game at Lambeau Field is also one of the fun things to do. If you are a food lover, explore the city with a food tour or grab a drink at the Urban Beats Cafe.

It is best to visit the city in the summers to have a great vacation package from amazing accommodation at the best Airbnbs in Milwaukee to delicious food.

By Paulina Of Paulina On The Road

4. Madison, Wisconsin

Madison - Weekend Trips From Chicago
Madison – Weekend Trips From Chicago

Cheese curds. Green spaces. Beer. Art. Concerts. If any of those things appeal to you, Madison, Wisconsin is a great option for a weekend trip from Chicago. It’s a short two and a half hour drive. Many know it as a college town, but it’s so much more.

Madison is a growing culinary destination. While there, be sure to check out The Old Fashioned for all of Wisconsin’s finest: cheese curds, brats, beer cheese soup, and the namesake old fashioned cocktail. If you still have room, Ian’s Mac and Cheese Pizza is not to be missed. Wisconsin is America’s Dairyland after all.

During your visit, stop by the Wisconsin State Capitol building. It’s the only state capitol building with a granite dome and they offer free tours daily. And to get your fresh air fix, take in the views of nearby Lake Monona from Monona Terrace. Check out the event schedule in advance to catch a concert here. Madison is a great destination year round, but it shines in the summer when outdoor activities are in full swing.

Where To Stay: We did also recommend the adjoining Hilton Madison Monona Terrace for incredible views of Lake Monona (not a bad view to wake up to).

By Brittany Of Family On Standby

5. Grand Rapids, Michigan

Grand Rapids - Weekend Trips From Chicago
Grand Rapids – Weekend Trips From Chicago

One of the most incredible weekend trips from Chicago is the charming Michigan city of Grand Rapids. In recent years, Grand Rapids has experienced a rebirth and is attracting the attention of travelers from the Midwest and beyond. Grand Rapids is about 30 minutes east of Lake Michigan and is the state’s second-largest city. It’s full of exciting museums, delicious food, and beer scenes and there are so many other things to do in Grand Rapids.

Out of the city’s many museums, the one to prioritize for a weekend trip is the Gerald R. Ford Presidential Museum. It’s full of artifacts that tell the story of the former president’s life and service to the country. If you have time, Grand Rapids is also home to two art museums and a museum of African American Museums. The city also boasts over 80 breweries, perfect to sample over a long weekend away from Chicago. Among the best is the well-known Founders Brewing Company, open daily for tours and tastings.

Where To Stay : Amway Grand Plaza Hotel for amazing views.

By Derek & Mike Of Robe-Trotting

6. Holland, Michigan

Holland Tulips - Weekend Trips From Chicago
Holland Tulips – Weekend Trips From Chicago

Located under 3 hours from Chicago is Holland, one of the prettiest holiday destinations in Michigan. The town’s inspiration from the Dutch’s history and culture can be seen through it’s fabulous floral farmlands, windmill spots, museums, lakes and greenness. The town is also known for hosting the delightful Tulip Time Festival every year during the spring season. There are millions of blooming tulips, bulb fields and various gorgeous flowerbeds that make the festival a magnificent spectacle of colors and scents. Visitors can also enjoy various flower shows, arcades, rides and parades held here throughout festive season.

Holland is home to the Big Red Lighthouse that dates back to 1872. You can see this historical landmark from the shores of Lake Michigan in the Holland State Park. This well preserved, around 250 years old windmill located on the Windmill Island Gardens also adds more to Holland’s Dutch inspired traditional landscape.

Another delightful place in Holland is the Nelis Dutch Village. It combines the charming medieval decors with wonderful displays of world-class Dutch cheese. A trip to this Dutch village is like an amazing journey that takes you through the Dutch culture and traditions. If you want to see a place in USA that gives you the feel of visiting Netherlands, then Holland is the p;ace for you to visit. The best time to visit Holland is during spring season that falls between March and May. This time is when the tulip fields are in full bloom.

Where To Stay : Hampton Inn

7. Beloit, Wisconsin

Ironworks Campus street art in Beloit Wisconsin - Weekend Trips From Chicago
Ironworks Campus street art in Beloit Wisconsin – Weekend Trips From Chicago

Just across the Wisconsin state line, about 90 minutes from Chicago, is the cute town of Beloit. Popular things to do in Beloit Wisconsin focus on the college and river. Sign up for a student-led tour of Beloit College and learn about the effigy mounds and World Affairs Center (funded by Andrew Carnegie’s only gift to a university). Logan Museum of Anthropology houses an enviable collection of Native and Latin American pottery and baskets. Ask about their connection to Indiana Jones.

A summer visit is recommended, especially to attend the Friday night summer concert series along Rock River. Spend overnight at the phenomenal Ironworks Hotel and visit the amazing Beloit Farmers’ Market on Saturday morning. Stock up on fresh produce and goods, then enjoy meals at local favorites like Truk’t, Lucy’s #7 Burger Bar, Bushel & Pecks, 615 Club, Velvet Buffalo, and Merrill and Houston’s.

Explore Ironworks Campus across the river from Ironworks Hotel. The one-million square foot repurposed factory is interesting to walk around and now houses local businesses. Head another 20 minutes north to Janesville and explore the gorgeous Rotary Botanic Gardens and take a short hike to Devil’s Staircase on the Ice Age Trail.

Where To Stay : Ironworks Hotel

By Charles McCool Of McCool Travel

8. Champaign, Illinois

Champaign - Weekend Trips From Chicago
Champaign – Weekend Trips From Chicago

Urbana Champaign is a very small twin county University town which is at approximately 199 km from Chicago. By road trip you take approximately 3 hours to reach here.

Located amidst corn fields, this county boasts of one of the best University in the country. Not only this place is famous for world-famous University but there are many nature trails all around. Farms, Barns, Nature trails, Wine tours, gardens, sports, Lincoln’s museum, golfing are very common things to do in Urbana Champaign.

Also there are many famous spots in Campus town where you can find various activities like watching famous theatre or art show at University auditorium. Many world famous events are held here and people all around from neighboring cities visit here to witness them. Christmas markets and Light show during Christmas is also very famous here.

Being a University town, this county also has many restaurants from diverse cuisines all around the world. Not only restaurants but you will find many hotels, here. Being a famous University town, not only boutique hotels, but you would find all kind of hotels branded and non-branded here. When students arrive for academic year then these hotels are always full and you would find difficult to find your stay here. But rest of the time, hotels are not over-priced and you can find rooms in budget too.

Where To Stay : Home2 Suites by Hilton Champaign

By Yukti Agarwal Of Travel With Me 24×7

9. Springfield, Illinois

abraham lincoln house springfield
Abraham Lincoln House Springfield – Weekend Trips From Chicago

Springfield, a quick three hour trip from Chicago, is the capital of Illinois and, perhaps even more famously, the home of the beloved president Abraham Lincoln, who lived here from 1844 to 1861. The city features museums and other relics from Lincoln’s life, including the not-to-be-missed Abraham Lincoln Presidential Library and Museum, a state-of-the-art institution detailing the 16th president’s life from birth through his time in the White House, the Civil War, and his untimely death.

Once you’ve gotten a good overview of his life, head to the preserved town of New Salem, where Lincoln served as a postmaster and rail-splitter and became the man that would eventually lead the United States through the tumultuous Civil War. Finally, close out your exploration into Lincoln’s life by stopping at his tomb, where his remains lie, along with those of his wife and three of his four sons.

There’s a large bronze sculpture of Lincoln at the entrance of the tomb- like the hundreds of thousands of other visitors from around the world here, be sure to rub his nose on your way out for good luck!

Where To Stay : President Abraham Lincoln – A Doubletree by Hilton Hotel

By Jessica Of Uprooted Traveler

10. Cleveland, Ohio

cuyahoga national park
Cuyahoga National Park – Weekend Trips From Chicago

When it comes to best weekend trips from Chicago, Cleveland should not be missed. Located in Ohio, and just over a five hour drive, this bustling city has something for everyone. 

Best things to do in the city include seeing the Christmas Story House (you can even stay the night!), Cuyahoga Valley National Park (the only national park in Ohio) do the ledges trail, this is a top bucket list experience, The Rock and Roll Hall of Fame, visit the Botanical Garden, visit Maria’s Field of Hope (when in season) to see the sunflowers, shop at The Arcade, and see the Museum of Art. Check out the Brewnuts Donuts for the maple bacon and Rowley Inn for the pierogi poutine.

One could argue all year is the best time to visit, depending on what you want to do, but spring – late fall is the best for weather.

Where To Stay : Definitely check out the Christmas Story House for a unique lodging experience!

By Nicole Sunderland Of Bucket List Lists 

Have we missed out any exceptional weekend trips from Chicago, that you really enjoyed? Share with us in the comments section below

Read Next

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.

%d bloggers like this: