Living in the hustle and bustle of Chicago is incredible, but sometimes it’s just exciting to hit the pause button, pack the car, and hit the open road for a road trip. The great thing about living here is how perfectly positioned the city is for a quick weekend getaway.
The Midwest is filled with hidden gems, charming towns, and a bunch of natural wonders. And they’re all within a reasonable drive from the city. In this guide, we’ve found the best places to take your family on a road trip, all within a 4.5 hour drive from Chicago.
That means if you leave in the morning, you’ll make it in time for lunch somewhere new! Whether that’s another big city in a neighboring state or a charming smaller town along the way, you’ll find lots to do and discover that will give you lots to talk about on the drive back home.
Join the Ben Lalez Team and let’s look at all the best road trips you can take from Chicago.
Big City Adventures
Milwaukee, Wisconsin (1.5 hours)
Milwaukee feels like a smaller and more relaxed Chicago. You can check out places like the Milwaukee County Zoo, the art museum right on the lake, or you can tour a brewery. The downtown area is very walkable, and parking is much cheaper than in Chicago.
Indianapolis, Indiana (3 hours)
This is another city with a very walkable downtown. You’ll find The Children’s Museum, which is the largest in the world and worth the trip alone. White River State Park connects most major attractions, and you can spend a day at the zoo or catch a Colts or Pacers game (depending on the season).
Cincinnati, Ohio (4.5 hours)
Cincinnati sits on the Ohio River, and you’ll have great views from both the Ohio and Kentucky sides. The zoo is one of the best in the country, and your family will enjoy all the activities at the riverfront park. Try the local chili! It’s served over spaghetti and is different than what you’re used to!
St. Louis, Missouri (4.5 hours)
Home to the famous Gateway Arch, you’ll find many free attractions, including the zoo and science center. Check out the City Museum because it isn’t actually a museum – it’s a massive indoor/outdoor playground built from reclaimed materials. How do they describe themselves? Weirdly Wonderful!
Detroit, Michigan (4.5 hours)
Detroit has come a long way from its dark years. The Henry Ford Museum in nearby Dearborn is worth the trip alone. It’s massive and covers everything from presidential limos to the civil rights movement. The downtown area has a nice riverwalk and Belle Isle Park, a 982 acre island in the Detroit River.
Chill Towns & Cultural Spots
Madison, Wisconsin (2 hours)
Situated between two lakes, Madison has a beautiful downtown centered around the Capitol building. The university gives the city energy and vibrance. The Saturday farmers market is one of the best in the Midwest, and the food scene is surprisingly excellent for a city of this size.
Bloomington-Normal, Illinois (2-2.5 hours)
Bloomington and its neighboring city Normal have a relaxed vibe with enough to keep you busy for a weekend. The Children’s Discovery Museum is highly rated, and the Constitution Trail offers miles of paved paths for walking or biking with the family.
Champaign-Urbana, Illinois (2.5 hours)
This is home to the University of Illinois and gives off a smart, laid-back feel. You can check out the Japan House for beautiful gardens, the Krannert Art Museum, or just enjoy the numerous delicious eateries that have popped up to serve the university community.
Springfield, Illinois (3 hours)
Springfield is all about Abraham Lincoln. You’ll absolutely want to visit The Presidential Library and Museum – they’re modern and engaging, not old and stuffy. You can also visit Lincoln’s home, his law office, and his tomb. Don’t forget to check out the Old State Capitol where he gave famous speeches.
Grand Rapids, Michigan (2.5 hours)
Once a furniture manufacturing town, Grand Rapids is now known for being a thriving arts scene. The downtown area has a ton of breweries to check out. You’ll also find good restaurants and museums along the river. For the art lovers, make sure to check out The Frederik Meijer Gardens where you’ll see sculptures combined with beautiful plant collections.
Iowa City, Iowa (4 hours)
Little known fact: Iowa City is the only UNESCO City of Literature in North America. Have a teen thinking about going to university here? The university campus is beautiful, and the downtown area has great bookstores. You’ll enjoy the relaxed, intellectual vibe throughout. And you can explore the pedestrian mall area where you’ll find plenty of restaurants and shops.
Spring Green, Wisconsin (4 hours)
This is a great small town to visit because it punches above its weight culturally. It’s home to Frank Lloyd Wright’s Taliesin estate and the American Players Theatre, which performs in a beautiful outdoor setting. Take a drive through the surrounding countryside to experience dramatic hills and valleys unlike the typical Midwest landscape.
Small Towns With Great Vibes
South Bend, Indiana (1.5 hours)
The Notre Dame Campus, with its golden dome and beautiful basilica, is where you’ll want to check out first. Other places of interest are The Studebaker Museum for classic cars, and the South Bend Chocolate Company for tours and chocolate samples! You’ll also find a revitalized downtown area with plenty to explore.
Rockford, Illinois (1.5 hours)
Outside of Japan, Rockford has one of the best Japanese gardens. For a peaceful retreat, make sure to check out Anderson Japanese Gardens. Don’t forget to check out the Discovery Center Museum and Burpee Museum during your stay, and you’ll enjoy the downtown area with restaurants in historic buildings.
Lake Geneva, Wisconsin (1.5 hours)
This has been a popular getaway for Chicagoans since the 1800s. Lake Geneva offers a 21-mile shoreline where you can walk past historic mansions or rent boats on the lake. Summers are lively with beaches and water activities. And the downtown area is known for being small but incredibly charming.
Holland, Michigan (2.5 hours)
Just like the name hints, Holland embraces Dutch heritage with a working windmill and millions of tulips that bloom every May. Make sure to visit the downtown area for nice shops and restaurants, and Holland State Park offers one of Michigan’s best beaches with the popular Big Red Lighthouse.
Peoria, Illinois (2.5 hours)
Here you’ll find a river town with a nice waterfront area where you can explore museums, restaurants, and plenty of places to walk. The kids will enjoy The Peoria Zoo and the Caterpillar Visitors Center (where you can climb on massive construction equipment). If you’re into nature, check out the Wildlife Prairie Park.
Fort Wayne, Indiana (2.5 hours)
Fort Wayne is a family-friendly place with a Fort Wayne’s Children’s Zoo, an interactive science museum, and botanical conservatory. Three rivers meet in the city center, and your family will enjoy Promenade Park downtown where you rent kayaks to take out on the water.
Saugatuck/Douglas, Michigan (2.5-3 hours)
These artsy beach towns feature Oval Beach which has massive sand dunes you can climb, and beautiful calm waters along Lake Michigan. The small downtowns have restaurants and shops that are a mix of art galleries, artisan gems, and quirky local culture. Try taking the hand-cranked chain ferry across the river just for fun.
Door County, Wisconsin (4 hours)
Door County is a 70-mile peninsula with shores lined with quaint lighthouses and charming small towns. It sorta feels like New England dropped into Wisconsin. Things to do include visiting state parks, watching a traditional fish boil, picking cherries in season, or just enjoying the small-town pace and natural beauty around you.
Traverse City, Michigan (4.5 hours)
This destination sits at the edge of our 4.5 hour radius, but it’s definitely worth the drive. Sleeping Bear Dunes National Lakeshore offers massive sand dunes with stunning views of Lake Michigan. This area is especially known for cherries and wineries, and you’ll want to check out all the great restaurants and shops downtown.
Bayfield & Apostle Islands, Wisconsin (4.5 hours)
For a more rugged getaway, head over to Lake Superior’s south shore. You can kayak through sea caves in the summer (or walk through ice caves in the winter). You can also take the ferry to Madeline Island or a boat tour of the 22 Apostle Islands to see lighthouses and wildlife.
Tips For Your Trip
- Call Ahead: Some smaller towns have limited hotel options that fill up fast, especially during peak season.
- Check The Weather: Pack layers and be flexible with outdoor plans – you know that Midwest weather can change pretty quickly.
- Get Off The Beaten Path: The best experiences come from talking to the locals when you arrive. Ask for recommendations at hotels and local shops.
Yes, we are The Ben Lalez Team and help buyers and sellers in Chicago. But we also know that Chicago’s central location really is the perfect place to plan road trips all across the Midwest.
Thinking about moving to Chicago? Contact our team today and we’ll be happy to give you a friendly Chicago welcome!
