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If you’re looking for a great road trip from Chicago, you have plenty of options to choose from. Depending on your interests, you could head north to explore the scenic beauty of Michigan, east to visit the historic sites of Ohio, south to experience the charm of Kentucky, or west to enjoy the natural wonders of Wisconsin.
No matter which direction you choose to go, you’re sure to find plenty of interesting things to see and do along the way. So gas up the car, get your road trip essentials, and hit the open road – there’s no better way to see the country than from behind the wheel of your own car.
St. Louis, Missouri
by Roxanna of Gypsy With a Day Job
One of the best road trips from Chicago is to St. Louis, Missouri. It is just over 300 miles, and about 5.5 hours of drive time on Interstate 55. Coming around the bend and seeing the Gateway Arch in the distance when approaching the city from that direction is exciting.
A first visit to St. Louis starts at the Gateway Arch National Park. While not a traditional National Park, it shouldn’t be passed up. The top of the Arch is an entirely different sensation than Willis Tower, with a different view. Don’t miss the critical civil rights site, the fun opportunity to learn the history of westward expansion from the city where it started, or a paddle-wheeler ride on the Muddy Mississippi.
After that, choose from an incredible 35 free things to do in St. Louis, which includes a world-class zoo with more animals than Brookfield; the historic brewery of the most popular beer in the US; the Ulysses S. Grant National Historic Park; the largest mosaic collection in the western hemisphere; the iconic Grant’s Farm where you can interact with the Clydesdales; and Unesco Heritage Site Cahokia Mounds. That only begins the list of free things to do!
You could also try unique St. Louis attractions like the National Blues Museum or City Museum. Before leaving, make sure to try St. Louis pizza at Imo’s, the polar opposite of Chicago style. For dessert, try an Ooey gooey butter cake where it originated.
by Taryn from Chasing Trail
Not quite a two-hour drive almost directly north, Milwaukee makes a perfect road trip destination from Chicago. Whether you’re making a quick day trip or staying a few days, you’ll find plenty to keep you busy.
Milwaukee, like Chicago, sits right on Lake Michigan, so during the summer, head to the lakeshore to take advantage of endless outdoor recreation opportunities. Walk or bike around the lake, paddle in a kayak or SUP, or take a sunset cruise. Year-round, visit the world-famous Harley-Davidson Museum (interesting even if you aren’t necessarily into motorcycles!), Milwaukee Public Market, or the Mitchell Park Domes, a unique botanical garden with several biomes.
While Chicago is a fantastic food city, Milwaukee is your go-to for all things beer. In fact, MiIlwaukee’s nickname is “Brew City” and major players, including Miller, Pabst Blue Ribbon, and Schlitz all started here. Today, the city is home to over 30 craft breweries. Must-visit standouts include Lakefront Brewery’s hilarious drink-while-you-walk tour and MobCraft, the only crowd-sourced brewery in the world. Several local companies offer brewery tours or “crawls,” where you visit several in one afternoon.
The Milwaukee Food Tour is something you don’t want to miss. It’s a great way to sample many delicious treats in an afternoon.
Finally, before you head back to Chicago, indulge in some of the Midwest’s finest gourmet foods: poutine, custard, and, best of all, cheese curds. Stop into Clock Shadow Creamery for fresh, made-on-site curds that actually squeak, or have brunch at Black Sheep MKE, right next door, for unique waffle-battered breakfast cheese curds!
Lake Geneva, Wisconsin
by Kyle at Viatravelers.com
Lake Geneva is a great road trip from Chicago because it’s a little bit closer than some other lakes in Wisconsin, but it’s still far enough away that you feel like you’re getting away from the city. Lake Geneva is a beautiful place to visit, especially in the summertime. It’s a quintessential Midwestern lake town, and as a result, it’s one of the best places to visit in the Midwest and a popular destination for Chicago residents.
The lake is gorgeous and plenty of activities keep you busy, whether you’re looking to relax on the beach or go for a swim or if you want to do some fishing or take a boat out on the water. The city also has some great restaurants and bars, so you can enjoy a meal or a drink while you’re here. And if you’re looking to do some shopping, there are plenty of stores to check out.
So whether you’re looking for a place to relax or have fun, Lake Geneva is a great choice. Lake Geneva is worth considering if you’re looking for a great place to visit in Wisconsin. It’s a beautiful lake with plenty to do, and it’s close enough to Chicago that you can make a road trip out of it.
Explore the Beauty of Southern Illinois
From Ladona Stork at Walking The Parks
Cruise down I-57 for a beautiful drive into Southern Illinois. This 5-hour trip will take you into the wilderness of the Shawnee National Forest. Here you’ll find fantastic hiking, adorable rentals, and a trail of charming wineries. Chicagoans visiting Southern Illinois for the first time are often surprised by its rolling hills and beautiful vistas.
Over 20 wineries dot the country roads of Southern Illinois. In the summer, their lawns are bustling as families and pets join the fun. Many wineries feature live music on the weekends. Or grab a Shawnee Hills Wine Trail map and spend the weekend touring.
If wine isn’t your beverage, check out the Southern Illinois Beer Trail. A dozen local breweries serve fine craft beers. You’ll also find unique distilleries sprinkled in.
The Shawnee National Forest is where you break out your bike or hiking shoes. Tunnel Hill State Trail, a 45-mile biking and hiking path on an old railroad bed, passes through undisturbed areas of the Shawnee National Forest.
Discover one of Illinois’ unique State Parks. Garden of the Gods is a popular stop, perfect for families due to its easy hiking trails and breathtaking views. Or travel to Cave-in-Rock State Park, nestled high on the rock bluffs along the Ohio River. Enjoy exploring the huge open cave with stories of river pirates and bootleggers.
While you’ll find traditional chain hotels along I57, the opportunity for more intriguing lodging prevails. Discover everything from treehouses, tiny houses, and deluxe log cabins among the rentals available.
by Paulina of Paulinaontheroad.com
Kenosha is one of the best destinations from Chicago on a road trip. It is just 66 miles from Chicago and takes about one hour and 12 minutes by road.
Kenosha is situated in the southeasternmost part of Wisconsin. It is one of the most worth-visiting destinations near Chicago because it has more than the usual brats and beer. It is a small town of one lakh people and is the fourth-largest metro area in Wisconsin. It has the most amusing and oldest running velodrome, classic old restaurants, two beautiful lighthouses, and a dinosaur museum that is free to visit. Travelers can even enjoy electric trolleys.
There are a lot of things to do in Kenosha. On your visit, make your way to the large, free, exquisite, and wonderful museums in the city. Kenosha History Center is among the most fascinating places to explore. Explore the rich history of Kenosha by stepping inside this big building. You will find collections that speak history.
After that, visit Kenosha Southport Lighthouse and the Lighthouse keeper’s home. It is situated at the lakefront and stands 55 feet tall. It was built in 1866 and was the center of guiding ships in the harbor for over 40 years.
In addition to lighthouses and museums, Kenosha is also home to historic restaurants and delicious beer. Enjoy classic German cuisine and satisfying beer at restaurants like House of Gerhard.
by Martin of Travelexplorator.com
Recommended by Rebecca from Veggies Abroad
Just a 5-hr. drive or Amtrak ride from Chicago will get you to the land of Motown and automobiles — Detroit.
While Detroit has a long history of both topics, there are many other things to enjoy, making it a worthy road trip destination from Chicago. Year-round visitors can enjoy a variety of cultural institutions (Detroit Institute of Arts, Motown Museum, Museum of African American History, to name a few), countless outdoor music festivals and fairs, a historic market, and even a little green space to stretch your legs or relax.
Any visit to Detroit isn’t complete without checking out the bustling historic Eastern Market (the best time to visit is on a Saturday). The market is a terrific place to peruse hundreds of vendors selling artisanal products, prepared foods, and loads of fresh fruits and veggies. Aside from that, the neighborhood surrounding the market is filled with countless shops, from tees proclaiming your love for the Motor City to antiques and everything in between — it’s hands down one of the best things to do in Detroit!
After visiting Eastern Market, head downtown to check out independent boutiques, drink on the beach in Campus Martius, and maybe even round out the day with a ballgame at Comerica Park or a show at The Fox Theatre.
There are dozens of other road trips you can take from Chicago. This list is just a jumping-off point with some spectacular things to do. So grab your kids and head off on one of the road trips from Chicago around the Midwest.
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