Gorgeous Summer Road Trips for When You Need to Escape Chicago
For when you need a quick reset.
Ah summer time. ‘Tis the best season in Chicago, a time when winter is a distant memory and everyone is blessed a rejuvenated verve for travel, outdoor adventure, and road trips. Conveniently, the Windy City is within spitting distance of ample road trip fodder, ripe for long weekends or even just a long afternoon. From brewery crawls in Michigan to hiking trails, museums, and bourbon bars at the fringe of Bourbon Country, here are 12 great road trip destinations for a quick getaway.
Distance from Chicago: 4.5 hour drive
The crossroads of the Midwest and the South, Covington is a northern Kentucky town—located right over the Ohio River from Cincinnati—that’s equal parts boozy, beautiful, and surprisingly metropolitan. While comparatively small next to Cincy, with around 40,000 people, Covington punches well above its weight, with a wealth of big-city amenities to keep you satiated and sloshed. Regarded as the gateway to Bourbon Country, Covington features a self-guided bourbon trail called The B-Line, mapping out distilleries, bars, and boozy restaurants, like New Riff Distilling, Boone County Distilling Co., Neeley Family Distillery, Old Kentucky Bourbon Bar, and Second Sight Spirits, the latter of which is a mystical mainstay in Ludlow, owned by two friends who met while working for Cirque du Soleil, with magic-themed decor, like a Houdini-shaped whiskey still. Keep the irreverent theme going with a visit to Vent Haven Museum, the only one in the world dedicated to the creepy-cool art of ventriloquism. Outside, travelers can flex their leg muscles and practice their fishing cast at Devou Park, drink in the views with a stroll over the John A. Roebling Suspension Bridge, or go shopping in colorful Mainstrasse Village, where boutiques and restaurants run the gamut from a gay-owned art store to Lisse Steakhuis.
Distance from Chicago: 5.5 hour drive
One of America’s fastest growing cities is ready for you. Eclipsing Indianapolis to become the second most populous city in the Midwest, along with the region’s second largest Pride festival, it’s a new kind of Second City that, much like our fair metropolis, excels at exceeding expectations. The local food scene alone is enough to compel a road trip, with its very own style of pizza (and a Pizza Trail to match) and a full-blown ice cream empire, which practically makes the entire city smell like fresh waffle cones. The Short North is like Columbus’ version of River North, teeming with rooftop bars, boutique storefronts, and the third largest concentration of fashion designers in the country, outside of New York and Los Angeles. Pop over to the Franklinton Arts District to gallery-hop and pair lawn games with IPAs at Land-Grant Brewing Company. Beyond beer gardens, the city boasts hundreds of acres of green space and urban trails, like Bicentennial Park and the 14-mile Olentangy Trail, with convenient pit stops like Understory, an airy school-turned-dining complex.
Distance from Chicago: 2 hour drive
South Bend sits just 95 miles from Chicago, which makes it a perfect day trip destination if you don't want to commit to a whole weekend away. One of the must-see attractions in the area is the breathtaking Basilica of the Sacred Heart, which was completed in 1888 and boasts the world's biggest collection of 19th-century French stained glass in the world. Meander along the St. Joseph River on the East Bank Trail, indulge in some sweets at South Bend Chocolate Company, or admire some vintage automobiles at the Studebaker Museum. You can also take a walking tour of the downtown area which is filled with historic homes, and for a truly unique overnight experience, book a room at the historic landmark Oliver Inn, a charming bed and breakfast. If you’re craving nature, nearby Potato Creek State Park offers plenty of hiking trails that take you along woodlands, prairies and wetlands.
Distance from Chicago: 3 hour drive
Grand Rapids, once known as “furniture city” for its fine wood furniture manufacturing, is now known as “Beer City”, because, well, all the beer. Throughout the metropolis you’ll find countless breweries like Founders Brewing, Brewery Vivant, and Saugatuck Brewing Co., and more. There’s also no dearth of restaurants either, like Terra GR, a downtown farm to table favorite, and Forty Acres Soul Kitchen, an elevated soul food and cognac bar. Hike and bike through Millenium Park or catch a live show with The Grand Rapids Symphony. Nothing here sounding appealing? Check out this ultimate weekend cheat sheet.
Distance from Chicago: 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 41 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.
Distance from Chicago: 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. Hike until your heart's content, and then order a cocktail or beer from any of the local bars (Robin Room, The Malt House, Working Draft Beer Company, Cask & Ale). There are plenty of drivable country activities, but the University of Wisconsin Arboretum is nestled closely within the city proper and has a variety of diverse paved and dirt trails. 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.
Distance from Chicago: 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 frozen 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. Wherever you stay though, there is plenty to do in and near Ottawa.
Distance from Chicago: 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 is a great place to enjoy winter outdoor activities boasting a number of cool bluff hikes overlooking the Mighty Mississippi. Another hiking option includes the historic Stagecoach Trail outside town and nearby Apple River Canyon State Park. Stay off General Grant's beaten path at the snug LeFevre Inn which is nestled on 100 acres of land just outside of town.
Distance from Chicago: 2.5-hour drive
This charming little hideaway about 30 minutes west of Sheboygan is often overlooked 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. The AAA Four Diamond Osthoff Resort is a popular choice, 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 on your keister enjoying the view from the Osthoff’s private beach or the public Fireman’s Park. Fall classics include brew tastings, hiking, biking, and no one ever hated on a crisp drive through Kettle Moraine.
Distance from Chicago: 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. Warm up by 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 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 winter serenity at nearby parks The Parkland of Floyd Fork and Cherokee Park.
Distance from Chicago: 5.5-hour drive
If you’re looking for the great Wisconsin Northwoods experience, it’s time to point your GPS towards under-the-radar Vilas County. 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 cozy cabins to luxury glampsites.
Distance from Chicago: 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.