One of the best things about living in Illinois and the Midwest, in general, is its accessibility and the fact that you can get to seven other states in a matter of hours. If the concrete jungle walls start caving in and the urban sprawl feels a bit claustrophobic, simply jump in the car and go for a drive. If you feel like you need to escape the hustle and bustle of city life, it’s easy to hit the road for a weekend or even day trip. Whenever you’re looking for a quick trip out of the Windy City, here are the best road trips from Chicago.
Just a short drive from Chicago, Lake Geneva is the perfect weekend escape—offering sparkling waters, charming shops, and a breath of fresh, small-town air with big getaway vibes.
Lake Geneva – For R&R on the Water
1.5 Hours from Chicago
If you’re looking for a short day trip from Chicago, Lake Geneva is one of the best beach towns in the Midwest without fighting the throngs of people at North Avenue or along the Gold Coast, where you can spread out and breathe.
If you’re hoping to soak in the sand and sun, you can stop by Big Foot Beach State Park, Lake Geneva Public Beach, or Riviera Beach. If you’d prefer to do a little hiking, you can tackle the Lake Geneva Shore Path or one of Big Foot Beach State Park trails.
But beach hopping and hiking are far from the only nature activities to do in Lake Geneva. You can also go camping, ziplining, skiing, sledding, and so much more, making it a fun year-round retreat.
Where to Stay: As a former Playboy Club, the Grand Geneva Resort is the most iconic property, but there are plenty of other options.
Milwaukee is Chicago’s cooler little cousin—easy to get to, full of character, and packed with craft beer, lakefront views, and just the right amount of weird.
Milwaukee – For Brews and Tunes
1.5 Hours from Chicago
Known as the mini Windy City, Milwaukee is another great weekend trip from Chicago for a less chaotic version of the “big city.” An up and coming cosmopolitan hub, their food, beer, and music scene is quickly becoming a magnet for millennials that’s infinitely cheaper than Chicago. And as a bonus? You don’t even have to drive if you don’t want to, as the Amtrak train goes right there.
Art aficionados can pay a visit to the Milwaukee Art Museum. History or beer buffs can spend a few hours at the Pabst Mansion. Animal lovers can say hello to all the friendly friends at the Milwaukee County Zoo. And motorcycle enthusiasts can spend an entire day at the Harley-Davidson Museum.
And while those activities are ideal for the daytime, enjoy the brews and tunes after dark. For a night of fantastic drinks and equally amazing music, stop by Company Brewing, Anodyne Coffee Roasting Company, or Milwaukee Ale House. You’ll definitely want to visit during Summerfest, which boasts two-weeks of back-to-back concerts on the lake.
Where to Stay: Milwaukee has a huge range of accommodation options, from penthouse apartments to trendy b&bs downtown.
One of the best spots to snag a B&B and snuggle up, Galena was voted one of the best small towns in the US for its history, architecture, and outdoor attractions. Eighty-five percent of the town’s buildings are listed on the National Register Historic District.
You can learn about the town’s mining history at the Elizabeth History Museum, wander around Main Street, visit President Ulysses S. Grant’s former home, go for a ghost tour, or hike the Galena River Trail. Unique period attractions like candle making, coffee cupping, goat trekking, and spoon carving will have you feeling far removed from city life in no time.
Where to Stay: The DeSoto House Hotel has hosted dignitaries like Abraham Lincoln and Stephen A. Douglas that retains its historic charm.
The waterpark capital of the world, Wisconsin Dells is home to the largest concentration of indoor and outdoor waterparks on Earth, with over 20 different places to splash around. In other words, it’s one of the best road trips from Chicago for families, especially if you’re looking to beat the heat in the summertime.
You and your family can race down the slides at Noah’s Ark Waterpark, get a thrill on the Bigfoot Zipline, ride the adrenaline-pumping rides of Mt. Olympus Waterpark and Theme Park, or visit the Kalahari Indoor Waterpark.
When you’re ready to dry off, say hello to the friendly animals at the Wisconsin Deer Park, go on a horse and carriage ride through the gorgeous Lost Canyon, catch a captivating show at the Rick Wilcox Magic Theater, and eat your weight in fudge at the old-timey candy shops downtown.
Where to Stay: Appealing primarily to family travelers, Wisconsin Dells has a range of budget-friendly motels and lakefront cabins.
Ann Arbor is great beyond game day, a city that blends brainy college-town energy with indie charm.
Ann Arbor – To Relive Your College Days
3.5 Hours from Chicago
Home to the University of Michigan, Ann Arbor is the perfect place to forget the real world’s stresses and act like a college kid again. You can tour the campus, visit one of the 16 on-campus museums, stroll the Matthaei Botanical Garden and Nichols Arboretum (the “Arb” to locals, catch a football game at “The Big House,” or simply drink the day away. Catch some live music at The Ark, peruse the Ann Arbor Farmers Market, tour a local craft brewery, and grab a bite from the iconic Zingerman’s Deli.
It’s a bit of a choose your own adventure as there is kayaking, canoeing, tubing, and stand-up paddleboarding on the Huron River in the summer, and cross-country skiing, snowshoeing, and ice skating in the wintertime.
Where to Stay: Close to campus, most hotels are easy and accessible for visiting students and parents, but if you’re looking for more of an urban retreat, you can also pop over to Detroit for the evening.
Door County is undoubtably one of the best road trip trips from Chicago for cozy, coastal escape energy you didn’t know Wisconsin could serve.
Door County – For a Nature Reprieve
3.5 Hours from Chicago
Nature lovers, this one’s for you. Door County in “Wisconsin’s thumb” is regularly regarded as one of the most beautiful spots in the Midwest, and it’s packed with things to do.
Outdoor attractions in Door County run the gamut from easy and relaxing to adrenaline-pumping and adventurous. You can dive to shipwrecks in Lake Michigan, kayak around Cave Point County Park, take a high-speed boat tour to see the lighthouses, or stroll around Fragrant Isle Lavender Farm & Shop.
While nature is the main highlight of Door County, the food scene is also quite noteworthy. You can take part in a traditional fish boil (watch your eyebrows, the fire is no joke), tour a winery or two, try a juicy cherry pie, and see the infamous goats on the roof of Al Johnson’s Swedish Restaurant.
If you’re looking for a longer getaway, consider adding in Milwaukee and Green Bay stops since they’re already on the way!
Where to Stay: Door County is actually like a dozen sleepy lake towns in one, so you need first to decide which side of the peninsula you want to be on. Sturgeon Bay is the most developed, but if you’re looking to get more off the grid, Baileys Harbor may be better suited for you. Sister Bay is right in the middle, which offers the best access to nearly everywhere.
St. Louis delivers more than just the Gateway Arch—think bluesy vibes, bold BBQ, and a surprising mix of culture and kitsch that makes it well worth the drive from Chicago.
St. Louis – For an Urban Escape
4.5 Hours from Chicago
Many people overlook St. Louis as an old and historical city, but it actually has amazing up-and-coming art and culture scene.
Of course, one of the best things to do in St. Louis is to visit the iconic Gateway Arch, which you can climb inside. This 630-foot stainless steel structure was built in 1963 and celebrates the westward expansion of the United States.
And while visiting the Gateway Arch (and one of the newest national parks) should be at the top of your St. Louis bucket list, there are plenty of other activities that you’ll want to add to your itinerary. Explore the new Union Station and see the city from the Wheel, experience the brand-new virtual reality ride at the St. Louis Aquarium, tour the insane architectural wonder that is City Museum, stop and smell the roses at the Missouri Botanical Garden, explore the 1,300 acres of St. Louis’ Forest Park, and admire the Cathedral Basilica of St. Louis.
To make your visit to St. Louis one of the best road trips from Chicago, you can add a few stops on your way like Peoria and Springfield, which are part of the iconic Route 66.
Where to Stay:The Angad Arts Hotel is a super cool boutique property that lets you book rooms by color to control your vibe— looking for romance? Go red. Want to relax? Choose blue. It’s totally up to you!
Route 66 started in Chicago, where the city’s energy meets the open road, setting off a legendary journey westward filled with iconic roadside attractions, hidden gems, and that unmistakable vintage charm.
Drive Chicago Route 66 – For the Ultimate Road Tripper
4 Hours from Chicago
The Chicago portion of Route 66 starts right in the heart of the city and winds its way to Collinsville, just outside of St. Louis. It’s the beginning segment of “The Mother Road,” which takes you across eight states, nearly 2500 miles, all the way to Los Angeles.
There are loads of memorable stops along this drive, making it one of the best road trips from Chicago. Downtown alone, you can visit The Bean in Millennium Park, take in the sights from Promontory Point, see the views from the Skydeck or 360 Chicago, and enjoy the famous Buckingham Fountain.
Once you get out of the city, there’s a host of other quirky attractions. You can dine on Venezuelan food at Chevere Latin Café in Joliet and tour the prison from Blues Brothers, visit The Route 66 Hall of Fame & Museum in Pontiac, Illinois, see the childhood home of Lincoln in Springfield, climb Cahokia Mounds, the largest prehistoric Native American site in North America, and snap a photo of the world’s largest catsup bottle in Collinsville.
Other fun photo ops en route include murals, old fuel stations, original brick roads, pink elephants, and kitschy diners.
Where to Stay: It’s primarily roadside motels along this route, but just 30-minutes from St. Louis, your best bet is to cross the border where you can splurge on a cosmopolitan escape or save on a budget property.
Road Trips from Chicago Take You from the Beaches Back Through History
Look, we love Chicago—we really do. But sometimes, you need a break from the honking, the traffic, and the 17-minute wait for the next train. Whether it’s lakeside lounging, small-town charm, or just a new horizon that isn’t blocked by skyscrapers, these road trips from Chicago are your sign to hit the pavement and breathe a little easier. So whether you’re chasing waterfalls, cheese curds, quirky roadside attractions, or just a little peace from the city’s sirens and street fests, there’s no shortage of open-road adventures waiting just beyond the skyline. Road trips from Chicago aren’t just getaways—they’re your Midwest-made excuse to roll the windows down, blast the nostalgic bangers, and remind yourself that yes, the journey can be just as fun as the destination. Just don’t forget the snacks—or your toll pass.
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About the Author: Sarah Etinas is a travel writer based on the beautiful island of Oahu, Hawaii. When she’s not enjoying the stunning beaches and hikes of her home island, she’s going on exciting adventures all around the world. You can keep up with her travel experiences on her website, Borders & Bucket Lists.
https://thedownlo.com/wp-content/uploads/2019/10/route66chicago.jpg764750Lohttps://thedownlo.com/wp-content/uploads/2020/05/downlo_logo-no-tagline.pngLo2021-02-15 18:00:142025-05-05 16:11:56The Best Road Trips from Chicago
It’s easy to be trapped in the Chicago bubble, meaning things to do downtown and in neighborhoods close to downtown. You have inspired me to travel a little bit outside the city and visit some of the places you have mentioned. Thank you for creating this unique post 🙂
Such a helpful list! I’ve been planning some road trips from Chicago this summer and this list has left me inspired. Can’t wait to plan some upcoming adventures.
It’s easy to be trapped in the Chicago bubble, meaning things to do downtown and in neighborhoods close to downtown. You have inspired me to travel a little bit outside the city and visit some of the places you have mentioned. Thank you for creating this unique post 🙂
Such a helpful list! I’ve been planning some road trips from Chicago this summer and this list has left me inspired. Can’t wait to plan some upcoming adventures.