Perfect Summer Road Trips for When You Need to Escape Chicago

There are plenty of day trips near the Windy City when you need a quick reset.

With plenty of drivable and desirable destinations sitting just outside of Chicago, there’s really no need to fly off to some exotic island this summer. Plus, road trips are just the best. There’s nothing more freeing than cruising down an open road with nothing but vacation on your mind. Picture this: You're behind the wheel, your car is packed full of family, friends, and snacks, the breeze is flooding in through open windows, and you're blasting your favorite song as you drive toward a much deserved break. So, from lake plunges and nature hikes to booze tours and cozy cabin stays, here are 18 of the best natural areas, small towns, and cities only a blow away from the Windy City.

Getaway Barber Creek
Photo courtesy of Getaway Barber Creek

Distance from Chicago: 133 miles, 2.5-hour drive
Ever wanted to say, “Screw it all,” get rid of all your earthly belongings, and hole up in a hygge-ified tiny house in the middle of nowhere? Live out all your reclusive fantasies without actually tossing your stuff by booking a weekend in Grand Junction, a pastoral sliver of western Michigan about 15 minutes outside the lakefront hamlet of South Haven. That’s where you’ll find Getaway Barber Creek, a 79-acre dog-friendly glamp-ground outfitted with a handful of secluded cabins complete with parking spots, picnic tables, Adirondack chairs, and fire pits for all your marshmallow-melting needs. Each matte black hideaway is as practically appointed as it is aesthetically pleasing, stocked with a plush, super comfy bed, gorgeous floor-to-ceiling window, compact table, kitchenette with running water, and full bathroom with, yes, a real-deal shower.
Outside the confines of your oasis lies plenty of outdoorsy and less-outdoorsy activities, from hiking the converted railroad Kal-Haven Trail or sand-strewn Van Buren Park Dunes Trail to checking out the historic South Haven South Pierhead Light or stuffing yourself silly at area farm-to-table eateries and top notch breweries. Whatever you choose, embrace your new lifestyle—however temporary—by stashing your phone in the lockbox provided, cozying up with a good bottle of whiskey (preferably something camp-ready like Stillhouse), and reveling in the simplicity of it all.
Stay: Find a great Airbnb near Illinois Beach State Park

Wisconsin Department of Natural Resources
Devil's Lake State Park | Wisconsin Department of Natural Resources

Distance from Chicago: 213 miles northwest, 4 hour drive
Wisconsin Dells is known not only for its killer adult-friendly water parks, but also for the dells themselves; a magnificent gorge carved out by ancient glaciers, boasting mighty views of sandstone cliffs along the Wisconsin River. The Dells of the Wisconsin River State Natural Area encompasses 5 miles of trails along the curving river, and private boat tours will take you along the upper and lower dells where you can marvel at the landscape from a comfortable seat. The boat float will also give you the best views of enormous and unusual rock formations that are unique to the area. If that’s not enough, nearby Devil's Lake State Park in Baraboo has equal views worth seeing. Apart from literally an endless amount of theme parks and water parks, the town itself has many charming features that are perfect for a summer getaway, like quaint b&bs (Oak Hill and Cedar Lodge), tasty restaurants/ breweries, and plenty of options to get close to furry friends (Timbavati Wildlife Park & Wisconsin Deer Park).
Stay: Find a great Airbnb in Wisconsin Dells

Michigan City Lighthouse
Michigan City Lighthouse | Jaclyn Novak/Shutterstock

Distance from Chicago: 60 miles southeast, 1 hour drive
Only have time for a quick breather from the city? No problem. Michigan City Indiana is a charming town along the southern shoreline of Lake Michigan and neighbors the venerable and incredibly diverse landscape that is the Indiana Dunes. The two parks, Indiana Dunes State Park and Indiana Dunes National Park sport miles of sandswept mounds along the lake’s shores, and have many trails wandering through dense woodland, serene prairie, and swampy wetland areas that will no doubt excite with their splendor. The town itself is packed with things to do from shopping at the massive outlet mall, hitting up one of the town’s breweries, to eating locally at one of the town’s many yummy restaurants.
Stay: Find a great Airbnb in Michigan City, Indiana

Madison, Wisconsin
Madison, Wisconsin | SamuelJLi/Shutterstock

Distance from Chicago: 147 miles northwest, 2.5 hour drive
Madison, Wisconsin is special because it has all the city perks, like quality restaurants and historic venues, while also being surrounded by a plethora of nature-filled activities from hiking, and biking, to fishing and boating. Hike until your heart's content amongst the green trails, and then order a martini from any of the vibing local bars. (Robin Room, The Malt House, Working Draft Beer Company, Cask & Ale). There are plenty of drivable country and lakeside activities, but the University of Wisconsin Arboretum is nestled closely within the city proper and has a variety of diverse paved and dirt trails covering its eclectic landscape. You don’t have to be an architecture nerd to appreciate Frank Lloyd Wright's famous estate, Taliesin, and on your way back, you can visit Blue Mounds State Park, to enjoy some stellar views from the tallest point of this region of Wisconsin.
Stay: Find a great Airbnb in Madison, Wisconsin


Distance from Chicago: 80 miles northwest, 1.5-hour drive
There’s a reason why Lake Geneva has been Chicago’s number one vacation destination for generations. It’s got everything you could possibly need in a weekend oasis… all 90 minutes from the city. As one of America’s best lake towns, it boasts an array of activities from booze cruises and hot air balloon rides to a stomach-satisfying food and drink scene. Luckily, there are many ways to escape the crowded downtown from walking the entire length of the lake shore along the town’s uniquely open-to-the-public Lake Shore Path to hiding out in under-the-radar Lake Como, home of the epic Mars Resort and its newly expanded patio. The lesser-visited lakeside towns of Williams Bay, Fontana, and nearby Lake Delavan are also more than worthy of exploration.
Stay: Find a great Airbnb near Lake Geneva

Illinois Department of Natural Resources
Illinois Department of Natural Resources

Distance from Chicago: 46 miles north, 1.5 hour drive
Zion Illinois is a stunning lakeside town straddling Wisocnin’s border and will give you a serene intermission without the time commitment. The town’s chief attraction is the stunning 4,000-acre Illinois Beach State Park where you can recharge by meandering along its vast shoreline, biking their north to south trails, or hiking beneath the savannah oak trees. The town itself has several humble local hotel accommodations, but this state park is best to experience as a camper, so dust off that tent, pick up a bundle of firewood, and get cozy beneath the summer night sky. After traversing the state park, there are also numerous nearby forest preserves and river trails to experience like Van Patten Wood, Des Plaines River Trail, and the Pine Dunes Forest Preserve.
Stay: Find a great Airbnb near Illinois Beach State Park

Starved Rock State Park
Starved Rock State Park | Jason Patrick Ross/Shutterstock

Distance from Chicago: 94 miles southwest, 2-hour drive
The historic town of Ottawa, located at the intersection of the Fox and Illinois Rivers, is best known as the entryway to Starved Rock State Park, where tall bluffs and canyon waterfalls provide one of the finest outdoor experiences near Chicago. While it is the most popular state park in Illinois, Starved Rock still manages to create one of the finest hiking and camping destinations around with 18 glacier-carved canyons and more than 13 miles of trails. Don’t miss the equally cool bluff-side expanses of nearby Matthiessen or Buffalo Rock State Park. And if you can swing a room for the night at the National Register of Historic Places-listed Starved Rock Lodge, by all means, you should. You can even hop aboard a river cruise or tread alongside an expert on a guided hike tour. Wherever you stay though, there is plenty to do in and near Ottawa.
Stay: Find a great Airbnb near Starved Rock State Park

Historical Galena Town Main Street
Historical Galena Town Main Street | Nejdet Duzen/Shutterstock

Distance from Chicago: 164 miles northwest, 3-hour drive
As one of the best small towns in America, Galena has you covered if you're into strolling cobblestone streets amidst historic mansions and scenic rolling hills. With the entire Galena Historic District (home of more than 1,000 buildings constructed before 1900) listed on the National Register of Historic Places, you won’t have to wander far to realize why Ulysses S. Grant chose to make his home here. If you're feeling more outdoorsy, Galena also offers plenty of activities for the adventurous including rafting trips along the Mississippi River, ziplining at the nearby ski resort Chestnut Mountain, and a number of cool bluff hikes overlooking the Mighty Mississippi. Stay off General Grant's beaten path at the LeFevre Inn, nestled on 100 acres of land just outside of town. If you’re interested in a hike, some of your best bets include the historic Stagecoach Trail outside town and nearby Apple River Canyon State Park.
Stay: Find a great Airbnb near Galena

Oval Beach
Oval Beach | FotoKina/Shutterstock

Distance from Chicago: 139 miles northeast, 2.5-hour drive
Saugatuck is famous for the pristine Oval Beach (cited by the Tribune as the Midwest's best beach), where you can rent kayaks, cruise on sailboats, and kick back along 10 miles of prime Lake Michigan real estate. Sand dunes and paddle boat rides also vie for your attention at this Hampton-style retreat, but Saugatuck’s arts scene is what really sets it apart from the region’s numerous beach towns. Known as “the art coast of Michigan,” Saugatuck and the nearby towns of Douglas and Fennville are home to dozens of art galleries and unique shops tailor made for a laid-back meander through the gallery-lined downtown district. The open-minded community is also extremely accommodating to all lifestyles, with more than 140 LGBTQ-owned and gay-friendly businesses making it one of the most queer-friendly small resort towns in America.
Stay: Find a great Airbnb near Saugatuck

Road America
Road America

Distance from Chicago: 150 miles north, 2.5-hour drive
This charming little hideaway about 30 minutes west of Sheboygan is often overlooked by those seeking the classic lake town experience, but shouldn’t be. The laid-back, pretense-free 292-acre lake boasts some of the clearest waters in Wisconsin, in addition to some A-plus fishing and a famous nearby racetrack. The AAA Four Diamond Osthoff Resort is a popular choice on the lake, but the area also offers a wealth of nature to get lost in thanks to its location near the gorgeous 30,000-acre Kettle Moraine State Forest. Hike sections of Wisconsin’s 1,200-mile Ice Age National Scenic Trail, explore the area’s rolling hills via bike on the 17-mile Old Plank Road Trail, and be sure to spend some time cozied up on Elkhart Lake itself with a kayak, paddleboard, or on your keister enjoying the view from the Osthoff’s private beach or the public Fireman’s Park. Summer classics include brew tastings, water activities, hiking, biking, and no one ever hated on a sunny drive through Kettle Moraine.
Stay: Find a great Airbnb near Elkhart Lake

Anaway Place
Anaway Place

Distance from Chicago: 208 miles northwest, 3.5-hour drive
With seven spectacular cabins including the stunning glass-walled Meadow House, Candlewood Cabins in rural Richland County located about an hour west of Madison is a nature escape tailored for your summer getaway. Social distancing is no problem on the lush 80-acre property, which has no lobby or public gathering place. Each private cabin looks out into the rolling hills and scenic fields that surround the grounds, with some walking trails like The Ridge Road starting right at the foot of your cabin. Spot wildlife including birds and deer, grab a picnic with a bottle of wine in a grassy open field, or explore the 15-mile Pine River Recreation Trail by bike over an abandoned railroad line dotted with bridges. The area also boasts three nearby rivers with 267 miles of Class I and Class II trout fishing plus five state parks within an hour’s drive, including the 100-mile Lower Wisconsin River Scenic Byway.
Stay: Find a great Airbnb in Richland County

Wild Tomato Wood-Fired Pizza and Grille Fish Creek
Ridges Sanctuary | Wild Tomato Wood-Fired Pizza and Grille Fish Creek

Distance from Chicago: 276 miles north, 4.5-hour drive
Known as the “Cape Cod of the Midwest,” Door County is a picture-perfect assemblage of more than a dozen great little towns situated on a beautiful 75-mile peninsula surrounded by the shimmering waters of Lake Michigan and Green Bay. With 53 public beaches, five state parks, and 300 miles of shoreline, there's a lot to like (and do) here. Explore some of the area’s nature-filled destinations such as the 7,000 acres of pristine open space preserved by the Door County Land Trust or the peaceful lighthouse-dotted Ridges Sanctuary as you listen to nothing but the sound of the trees being swayed by the summer breeze. Limit your interaction with other humans by doing carry-out from a wealth of excellent local restaurants such as Wild Tomato, and be sure to check out other hidden natural gems such as Baileys Harbor Ridges County Park or the breathtaking Hotz Memorial Town Park. The area is also dense with summer activities from trolley tours and roadside farm stands to country stores and farmer's markets.
Stay: Find a great Airbnb in Door County

Sleeping Bear Dunes National Lakeshore
Sleeping Bear Dunes National Lakeshore

Distance from Chicago: 323 miles northeast, 5-hour drive
There’s no shortage of nice beaches near Chicago. Then again, there are no beaches quite like the absolutely stunning Sleeping Bear Dunes National Lakeshore. Yet one of the most gorgeous locations in the Midwest—complete with 35 miles of scenic coastline, forests, dunes, bluffs, and plenty of massive mounds of sand to roll around in—is not alone when it comes to eye-popping beach hopping near the charming resort town of Traverse City, located at Michigan’s northern tip. From the popular Clinch Park and Bryant Park beaches to the more remote Haserot and North Bar Lake beaches, stunning views of the Grand Traverse Bay await from a number of locations in town. You’re also within a stones throw of the coastal M-22, one of the most scenic drives in America.
StayFind a great Airbnb in Traverse City

The Parklands of Floyds Fork
The Parklands of Floyds Fork

Distance from Chicago: 300 miles, 5 hour drive
Louisville might be known for, you know, Kentucky fried chicken, and the Kentucky Derby, but there are actually so many more reasons to put this town on your bucket list. Walk through the bourbon district and sip your way around the many distilleries, from family-run favorite Peerless to well-known giant Evan Williams, or opt for the lighter stuff and get your fill of the bottomless breweries around town, like Chimera Brewing Company, Falls City Beer, Akasha Brewing Company, and more. Besides drinking, you can catch a thrilling Shakespearean show from the outdoor summer series Kentucky Shakespeare Festival that runs through August 7, meander through Louisville’s vibrant historic Frankfort Avenue, a 2.5-mile stretch of boutiques, galleries, restaurants, and bars, get cultured and visit one of their outstanding museums like Roots 101 African American Museum, Louisville Slugger Museum & Factory, or seek some serenity at nearby parks The Parkland of Floyd Fork and Cherokee Park.
Stay: Find a great Airbnb near Louisville

Point of View Lake Resort and Glamping Campground
Point of View Lake Resort and Glamping Campground

Distance from Chicago: 311 miles northwest, 5.5-hour drive
If you’re looking for the great Wisconsin Northwoods experience you’ve only heard about by drinking at Will’s Northwoods Inn, it’s time to point your GPS towards under-the-radar Vilas County. With one of the world’s largest collections of freshwater lakes, this outdoor purist’s paradise boasts more than 1,300 lakes and 73 rivers and streams. The charming tourist communities of Eagle River and Minocqua are essential area attractions, but for a better and more off-the-beaten path experience, check out the unrelentingly awesome Coadys’ Point of View Resort in the town of Phelps near Wisconsin’s border with Michigan’s Upper Peninsula. Tucked away on the peaceful shores of North Twin Lake within the massive 661,000-acre Nicolet National Forest, the resort offers everything from cabins and luxury glampsites to boat rentals on one of the finest musky fishing lakes in North America. The resort (run by former Chicagoans Darren and Genevieve Coady) are even offering contactless carry-out and delivery from its on-site general store.
Stay: Find a great Airbnb in Vilas County

Shawnee Hills Wine Trail
Shawnee Hills Wine Trail

Distance from Chicago: 351 miles southwest, 5.5-hour drive
No one is going to mistake Illinois for a natural wonderland, but the Land of Lincoln has one ace up its sleeve: Shawnee National Forest, a brilliant expanse of approximately 280,000 acres that covers a large portion of the southern tip of Illinois. In other words, it’s the perfect spot to take a much-deserved break from the endless crush of bad news for a few days. Bask in the solitude of the national forest’s epic Garden of the Gods Wilderness (one of seven wilderness areas in the park) before making a peaceful meander through the Shawnee Hills Wine Trail: a 35-mile scenic drive featuring 11 award-winning wineries dotted throughout rural countryside towns like Cobden, Alto Pass, and Pomona. All the wineries are currently open for indoor and outdoor seating, so bring your vax cards, and enjoy this nearly Rhode Island-sized national forest.
Stay: Find a great Airbnb near Shawnee National Forest

U.S. Forest Service
Pictured Rocks National Lakeshore | U.S. Forest Service

Distance from Chicago: 380 miles northeast, 6 hour drive
The upper peninsula of Michigan is a truly spectacular piece of the Midwest that is often overlooked by Chicagoans, as it does require more road time. But don’t let the distance discourage you. Pictured Rocks National Lakeshore includes 42 miles of glorious views along the southern dip of Lake Superior, and really packs a punch, with gushing waterfalls, pristine lakes, endless rugged forest, and multi-colored rocky ridges with some as high as 200 feet. You won’t want to miss the Miners Castle and Chapel Rock, both impressive craggy cliffs which stand apart from the rest because of their peculiar shapes and size. Whether you want to hike through the forest, kayak along the shoreline, cruise on a boat, or bike some backroads trails, this natural paradise will keep you occupied for a long summer weekend for sure. Fun fact, this area is widely known by historians to be the burial ground of many old ships dating back to as early as 1860. Book a tour on a boat with a glass floor to see these huge relics while you float above. Munising Township is stocked with restaurants, bars, and humble accommodations if camping doesn't sound appealing. Also, Hiawatha National Forest is 15 miles away so you get two for the price of one.
Stay: Find a great Airbnb near Pictured Rock National Lakeshore

Mackinac State Historic Parks
Mackinac State Historic Parks

Distance from Chicago: 413 miles, 6 hour and 20 minute drive
You will have to leave the car on the mainland and take a fairy to get to this vacation destination, but we promise it’s worth it. This northern Michigan island sits on Lake Huron and is unique not only because it has zero motor vehicles, but also because of its rich history, bottomless charm, and stunning beaches. Walk, bike, or ride a horse drawn carriage around town to shop at the various stores, taste delicious beer, learn about Mackinac’s history, and marvel at the historic cottages. The island’s state park, Mackinac Island State Park, has 70.5 miles of magical trails and roads where you’ll discover breathtaking views and geological formations including the impressive fifty foot wide Arch Rock.
Stay: Find a great Airbnb near Mackinac Island

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Elanor Bock is a Chicago born, New York-based professional dancer, writer, and renaissance woman, excelling at philosophy, mathematics, outdoor adventuring, and balancing six martinis on a tray in a crowded bar.
Jay Gentile writes about food & drink, travel, events, entertainment, and culture for Thrillist.