Fall is here, so it’s time to get away! While we adore our beloved Chicago, the Midwest is sprawling with beautiful and scenic cities within just a few hours of the city. Whether you want to get away to explore a stunning hiking trail or just spend the weekend roaming a charming town with cobblestone streets, there are tons of amazing things you can experience, so check out the best road trips from Chicago!
1. Madison, Wisconsin
First on our list is where Wisconsin’s capital is located, and it happens to be the second largest city in the state. Madison lies in the south-central part of the state and is centered on an isthmus between Lakes Mendota and Monona.
The proximity to the lakes makes waterside adventures a must; there are endless activities to participate in, between boating, kayaking, and swimming. After, take a stroll through the charming streets and head to one of the many breweries, or for an evening filled with serenity, head to the Olbrich Botanical Gardens, where Oblrich’s Thai Pavilion is located and is the only one in the US, and the only one outside of Thailand surrounded by a garden.
🚗 Distance from Chicago: 148 miles
🕐Arrival Time: 2 hr and 23 mi
2. Holland, Michigan
When people think of Holland, what usually comes to mind is the Keukenhof Tulip Gardens in Amsterdam, Holland. However, you don’t need to buy an international plane ticket when another Holland is only a few hours away. This road trip from Chicago will be your new favorite getaway.
While in Holland, you’ll be able to indulge in Dutch experiences such as sprawling tulip gardens, cobblestone streets, and the picturesque Tunnel Park. With over 100 specialty shops, breweries, and restaurants, this is the perfect place to head on a road trip.
🚗 Distance from Chicago: 150.8 miles
🕐Arrival Time: 2 hr 25 min
3. Traverse City, Michigan
One of our favorite Chicago trips, known as the “Cherry Capital” of the world, it’s easy to get lost in the beauty of Traverse City. Stroll along the shoreline at Grand Traverse Bay and glance at the fluid waves as you take in a majestic sunset.
While there are many things to do in Traverse City, some of our highlights include touring the wineries, scaling a dune at the Sleeping Bear Dunes National Lakeshores, picking out some blum cherries, and immersing yourself in the beautiful lakeside town.
🚗 Distance from Chicago: 318.6 miles
🕐Arrival Time: 4 hr 55 min
4. St. Louis, Missouri
One of the major cities in Missouri, St. Louis, lies along the Mississippi River and displays an iconic 630-foot Gateway Arch built in the 1960s. St. Louis is a quintessential city to visit, with a vibrant arts and culture scene, lively bars, and acclaimed restaurants.
This is also one of the best road trips from Chicago if you’re a fan of Chicago baseball. With Busch Stadium nearby, schedule your road trip for a game between the Cardinals and the Cubs, one of the best rivalries.
🚗 Distance from Chicago: 298.8 miles
🕐Arrival Time: 4 hr 28 min
5. Bloomington, Indiana
Bloomington is most notably known as the home for students of Indiana University. Nestled in the rolling hills of southern Indiana, the city has spectacular foliage surrounding the town as you drive in.
Along with the visually stunning scenery, there is vibrant art, spectacular shopping, and notable restaurants—all of which support the thriving local business scene. However, it wouldn’t be right to mention Bloomington without mentioning sports. With the Big Ten, rowdy football and basketball games are an innate part of the town.
🚗 Distance from Chicago: 232.3 miles
🕐Arrival Time: 3 hr 48 min
6. Columbus, Ohio
Along with Bloomington, Columbus is a celebrated city with a younger population due to the booming tech industry and innovative arts scene. As Ohio’s state capital, it’s one of the largest college campuses in the country.
This is one of the best road trips from Chicago if you’re looking for lively nightlife. Walking down High Street, you’ll be surrounded by reverberating music and packed patios, especially if the Buckeyes are playing.
🚗 Distance from Chicago: 356.5 miles
🕐Arrival Time: 5 hr 27 min
7. Wisconsin Dells, Wisconsin
Situated in southern Wisconsin, the Dells lies on the Wisconsin River in a region of glacier-carved sandstone formation and might be one of the most exhilarating cities on this lift. This is the best road trip near Chicago for any family planning an adventure-filled weekend.
There are numerous theme parks and entertainment centers, including Noah’s Ark Water Park and Mt. Olympus Water and Theme Park, both indoor and outdoor, spanned with waterslides, lazy rivers, rafts, and more!
🚗 Distance from Chicago: 193.5 miles
🕐Arrival Time: 2 hr 59 min
8. Saugatuck, MI
If you’re looking for award-winning beaches, scenic waterways, and verdant dunes, take a road trip to Saugatuck, Michigan. This is the ultimate escape for a quiet, luxurious weekend, with an animated art scene and renowned culinary restaurants. It’s a place that seamlessly switches from exploration to recreation for people visiting—making it one of the best road trips from Chicago.
🚗 Distance from Chicago: 145.8 miles
🕐Arrival Time: 2 hr 19 min
9. Ann Arbor, MI
While many of the Michigan cities listed here are located along Lake Michigan, Ann Arbor is one the few recognized as an urban oasis in the middle of the state. The downtown scene is from a storybook with a red-brick main street filled with independent bookstores, locally-made candle shops, home goods, and more.
While there’s a lot to do downtown, head outside the city to explore the nature parks surrounding the town, which have some of the most scenic hiking trails.
🚗 Distance from Chicago: 241.3 miles
🕐Arrival Time: 3 hr 45 min
10. Sheboygan, Wisconsin
Deemed the “Malibu of the Midwest,” Sheboygan, Michigan, might not have five-foot waves like the West Coast. Still, it’s a freshwater haven for anyone who loves fishing, sailing, and surfing; from outdoor recreational activities like golfing and biking to events and festivals that highlight the art scene, cultural heritage, and vibrant music, it’s no wonder it’s one of the best road trips from Chicago.
🚗 Distance from Chicago: 147.6 miles
🕐Arrival Time: 2 hr 24 min