Even if you live for summer in the greatest city on the planet, breaks are warranted. Whether you’re escaping big festivals that choke downtown or the Democratic National Convention’s swarm of lanyards, there are plenty of roads less traveled that are worth taking.
For this list, we narrowed travel time to under four hours and highlighted nature sojourns, tiny towns, architectural icons and more.
1. Indiana Dunes, Indiana
Less than 1 hour from the Loop
Need a break from the crowded city beaches? Jonesing to relive scenes from Dune? Less than an hour’s drive from downtown, the Indiana Dunes beckon. Protected by state and national park designations alike, these epic mountains of sand hug 15 miles of lakeshore accessible through a handful of entry points. The steep dunes are covered in trails bound to burn your glutes and calves, but the real draw in summer is the beaches.
Aptly named West Beach is the biggest and offers full-service amenities, including a bathhouse and all-day lifeguard, but its popularity attracts big crowds on hot days. For a more chill dunes beach experience, head further east to Kemil Beach, with picnic areas and access to the Dune Ridge Trail. For sustenance in nearby Chesterton, settle into a table for light Italian fare at the lovely Lucrezia Café or grab a spot at the bar at Craft House for local brews and pub grub.
2. Beverly Shores, Indiana
1 hour, 15 minutes from the Loop
Mid-century architecture buffs, this one’s for you. An easy drive from downtown (better yet, take Metra’s newly expanded South Shore Line), Beverly Shores is a planned resort community that dates to the early 1900s, but features homes that look marvelously modern thanks to its Century of Progress Architectural District.
This handful of private homes were originally built for the 1933 World’s Fair’s Homes of Tomorrow exhibition, and you can tour them on one single day in the fall — if you’re lucky enough to score tickets. Meanwhile, scenic drive-bys are complemented by sweet gift shops and vintage shops, e-bike and golf cart rentals to take to the beach, and the Beverly Shores Depot & Gallery, which has exhibits throughout the summer.
Jan Parr, a longtime Chicago media editor who moved to Beverly Shores five years ago, says she stops by Goblin & The Grocer to catch up with neighbors over a glass of wine. She also recommends the South Shore Ovenworks pizza truck, a bright orange Studebaker parked next to the Camp Stop at Broadway and Highway 12, with al fresco bench seating (grab craft beer or a bottle of wine at Hobgoblin next door).
3. Harbor Country, Michigan
About 1 hour, 15 minutes from the Loop
It’s difficult to pick a favorite town in this charming corner of southwest Michigan. Collectively known as “Harbor Country,” eight distinct hamlets straddle I-94 from the Michigan border to Warren Dunes State Park, each with its own personality and attractions.
The proverbial heart of the “Hamptons of the Midwest” is New Buffalo, whose handful of wineries, upscale shopping and lodging, and galleries lend it a slightly more cosmopolitan air than its neighboring towns. Melissa Lewis, principal at Melissa Lewis Interiors, recommends starting or ending your journey at the Whistle Stop for delectable sandwiches, snacks and baked goods.
Just up the road is Union Pier, where more wineries (including St. Julian, Michigan’s oldest), fine dining restaurants and antiques are complemented by posh inns.
A quick drive inland leads to the village of Three Oaks, the arts and cultural hub of Harbor Country. The Acorn Center for the Performing Arts hosts concerts, events and festivals year-round, and around the corner the Vickers Theatre shows new movies and old favorites. For lunch, grab a table at Froehlich’s and peruse the vast provisions shop while you wait. Pick up some award-winning whiskey at Journeyman before heading back to the city.
4. Lake Geneva, Wisconsin
1 hour, 45 minutes from the Loop
There’s a reason why so many wealthy Chicagoans of the Gilded Age sought to build holiday homes on Geneva Lake. The vast lake’s crystal-clear water, gentle breeze and rolling hills offered a welcome respite from the crowded city — and little has changed since. The so-called “Newport of the West” is still home to many of those tony mansions, which are visible from cruises on the lake. (Black Point Estate, one of the biggest, is also open for house tours.)
Beyond the mansions circling the shore, Lake Geneva is a quintessential resort town with a sweet little pier, lakeside walking trails, a smattering of ice cream parlors (check out Scoops just off Main Street), decent antiquing and a range of places to dine, drink and snack. There’s also a magic theater hosted by “master illusionist” Tristan Crist (you can’t miss his cheesy billboards on the way into town) and the truly beautiful Victorian-era Yerkes Observatory.
On the way from Chicago, don’t miss all the produce and provisions from surrounding farms. “When I’m driving up to [nearby] Elkhorn, I stop at River Valley Ranch for produce and miscellaneous pantry items, Lake Geneva Meats and Simple Bakery for the best seeded sourdough,” says Heidi Coudal, owner and culinary director at Big Delicious Planet. “And every weekend, we drive over to Rushing Waters Fisheries for fresh trout,” which supplies fish to several restaurants in Chicago.
5. Starved Rock State Park, Illinois
Two hours from the Loop
Looking to cool off from city life without braving the crowded beaches? Consider piling into the car for an easy drive to this vast state park, most of which is lushly shaded. Bring your boots or nonslip water sandals: Many of the park’s best walks and hikes weave around pretty waterfalls and moss-covered canyons (18 of them!), and wooden bridges carry greenery-starved pedestrians through about 13 miles of trails.
Fawn Julsaint, owner of the cleaning service My Deer Cleaner, visits Starved Rock with her daughter a few times a year for day and weekend trips. “We like doing the Wildcat Canyon trail,” she says. “It’s a 2-mile, moderate loop hike where you walk to several canyons and waterfalls and loop back along the Illinois River. It’s great for kids and families who aren’t prepared for a more adventurous 3- to 4-mile hike. The paths are well marked with colors on the posts and signs so you know where to go along the route.”
Beyond hiking, when’s the last time you visited a state park with its own concert series? The Veranda at the Starved Rock Lodge & Conference Center features al fresco dining and live music every Friday and Saturday night. Book a cabin or campsite, or stay in the beautifully historic lodge proper. Julsaint notes that overnighting also positions you to spend time at the neighboring Matthiessen State Park or stop at Jamie’s Outpost in nearby Utica for dinner and live music or karaoke. “And,” she says, “the trip is never complete without ice cream or sweets from Roxie’s Sweet Confections.”
6. Douglas and Saugatuck, Michigan
Two hours, 15 minutes from the Loop
If you’re looking to slow down a little — to appreciate a James Beard-worthy meal, to indulge in a beachside stroll, to ponder deeply meaningful creative interpretations of Lake Michigan and beyond — check out what’s referred to as the Art Coast of Michigan.
This pair of small, neighboring towns began building a reputation as a creative hub in the late 19th century’s Arts and Crafts movement. The most famous institution is the Ox-Bow School of Art, whose roots go back as far as 1910 and whose programming peaks in summer with Friday Night Open Studios, glorious al fresco monthly Culinary Events and Sunday Sojourns that pair tours of the vast campus with a laid-back brunch.
Oval Beach is the main sandy strip here (there are several others), but there’s more to the waterfront than Lake Michigan. Anne Godwin, an interior design and sales manager at home furnishings brand Ebanista, says the draws include an LGBTQ+ artist presence, top-tier establishments and a “super-friendly” vibe.
For a farm-to-table lunch or dinner, Godwin recommends Penny Royal Cafe & Provisions. Or for dinner, head to Phil’s for pad Thai and finish the night singing karaoke with the locals at the Corner Bar (Coral Gables), a “super-chill, no frills dive bar on the water.”
7. Kohler, Wisconsin
Three hours from the Loop
No, it’s not a toilet museum — though there are more than a few on display at the John Michael Kohler Arts Center. Kohler is the company town synonymous with the famous plumbing and bath fixture manufacturer. The traditional Tudor workers’ dormitory, opened as the American Club in the early 1900s, now operates as one of the most luxurious resorts in the Midwest.
It’s almost a three-hour drive, so consider saving up and booking an overnight visit to experience all the fine dining and monied recreation (think: fly fishing, golf, skeet shooting) — or, at the very least, the Kohler Waters Spa. This mecca of hydrotherapy spa treatments is closed for renovations this summer, but you can still pop in for nail services.
Beyond the resort, nearby Sheboygan offers small-town charm. Lizz Kannenberg, senior creative director at Chicago tech company Sprout Social, has collected favorites while spending time at her family’s lake house. “Majerley’s Black River Grill is the greatest of all supper clubs,” she says, noting a recent $22 bar tab for six old fashioneds. For caffeine and light bites, there’s Paradigm Coffee, a queer-friendly haven for great coffee, food and art. She also recommends That Place on 8th, a dive bar with a “pay what the owner (who goes by Tequila Kat) feels like” policy.
Finally, don’t miss the region’s signature Sheboygan Hard Rolls, a type of roll made only in the Sheboygan/Kohler area. With butter and jam or cheese, they’re a Wisconsin classic, and Kannenberg says Johnston’s or West Side bakeries are the best. Down the road, Kohler Park Dunes offers front-row seats to the Lake Michigan shoreline, and the little Tellen Woodland Sculpture Garden makes for a whimsical stop on the way up or back.
8. Galena, Illinois
Three hours from the Loop
Want to get a sense of what Chicago might have looked like if its historic 1800s buildings had survived the Great Chicago Fire? Spend the day — or a night — in Galena. Largely populated in the 1820s by settlers seeking out the area’s namesake ore, this truly charming small town features an architecturally award-winning main street nicknamed the “Helluva Half Mile.”
As one of the first streets in Illinois to require architectural reviews of its exterior building plans, Galena’s mid-1800s main street — which was given a facelift in the 2010s — is so aesthetically cohesive, it looks like a movie set.
The town is equally renowned as a home to numerous Civil War generals (eight!), most famously Ulysses S. Grant, whose home, a national landmark, is a must-visit. The city’s tourism bureau maintains a vibrant list of summer events, from concerts to tours. There are plenty of spots around town to grab a bite: Modern delis and sushi joints mixed in with throwback steakhouses, or splurge on dinner theater tickets to Amelia’s.
9. Mineral Point, Wisconsin
Three hours from the Loop
Settled around the same time as Galena, and for the same reason (a wealth of Galena ore), aptly named Mineral Point is a sweet spot in Wisconsin’s southwest region. Hilly steep streets, little log buildings and stone cottages lend it olden fairy tale vibes, but its cultural touchstones are timeless: artisan crafts, architecture and beer.
The community’s Shake Rag Alley nonprofit arts center is as beloved for its arts as its tidy acreage of gardens and stone paths, which come alive with pollinators in the summer months. The town’s original 1915 opera house was restored in 2008 as a “theatre for all the people,” which is reflected in its programming, from Eagles tributes to Loudon Wainwright III to screenings of current blockbuster movies.
Joel Reese, vice president of marketing and communications for the Chicagoland Chamber of Commerce, counts Mineral Point as one of his favorite places in Wisconsin, especially thanks to its bike-friendly rural roads and well-maintained trails. (“Shout-out to the perfectly named Cheese County Recreation Trail,” he says.)
Reese’s visits start with browsing shops including Brewery Pottery, which is just a little out of town. Then, a long bike ride to tire himself out, followed by a delicious meal with some home-crafted beers and fried cheese curds at Commerce Street Brewery (“How can you pass up a place that made several beers in honor of Betty White?” he jokes). It’s been around since the 1990s and has rooms for let upstairs in its beautifully restored 1854 warehouse.
It’s worth staying the night just to have a legit Cornish breakfast pasty at Red Rooster on High Street.
Spring Green is home to Frank Lloyd Wright’s infamous Taliesin.
Courtesy of Beth J. Harpaz/AP
10. Spring Green, Wisconsin
Three-and-a-half hours from the Loop
Though it’s a longer trek, this is one of the most rewarding drives on the list thanks to the increasing number of glorious green hills and barren blue skies once you’re past Madison.
This deceptively sleepy Midwestern hamlet is home to Frank Lloyd Wright’s infamous Taliesin: the so-called love nest he shared with a mistress before it was burned to the ground, killing his love and her children. The architect’s gravestone is down the road but his body isn’t. His remains are at the other Taliesin, in Arizona.
For lighter drama, grab tickets to the American Players Theatre a few miles east: a truly lovely amphitheater with exceptional theater productions and free concerts during summer weekdays.
Even more bizarre than Taliesin’s history is House on the Rock: a literal house built onto the chimney of a rock.
For a cozy breakfast or lunch, “I love the Spring Green General Store!” says City Lit Books owner Stephanie Kitchen, who often passes through while visiting extended family in the Driftless region. “There is a cute downtown area that includes a great local bookstore/cafe, Arcadia Books. I’d be remiss if I didn’t mention it!”
Lauren Viera has covered Chicago’s arts and cultural scenes for more than 20 years. She is the author of The 500 Hidden Secrets of Chicago (Luster) and lives in Logan Square.