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11 Best Weekend Getaways From Chicago

Condé Nast Traveler logo Condé Nast Traveler 6/24/2020 Nicole Schnitzler

With warmer months finally here, there’s never been a better time to roll down the windows, turn up the music, and hit the road for a nearby weekend getaway. Surrounded by college towns, state parks, and one Great Lake, Chicago is a prime starting point for many weekend jaunts—all beckoning their own adventure. And while several itineraries are doable as day trips, chances are you’ll enjoy the extra time away from home that a long weekend affords. From celebrated restaurants and book-ready beaches to renowned museums and starlit campsites, these destinations have something to make everyone in your road-tripping party equally eager to arrive.

a group of palm trees on a beach near a body of water © Getty

Indiana Dunes State Park, Indiana

Indiana Dunes State Park is more than 2,000 acres of sun, sand, and lakefront—but if that wasn’t enough, there’s the Dunes National Park, which spans more than 13,000 acres and whose annual tourism numbers rival those of Yellowstone. Regardless of the park you choose, you’ll have your pick of outdoor activities like biking, paddling, fishing, swimming, or hiking. If camping is on your summer to-do list, ready the RV or the tent—both parks have ample sites. The best part? Each is within walking distance to the beach, ensuring serene sunrise views—aka the ultimate wake-up call.

(About a one-hour drive)

a city street © Getty

Ann Arbor, Michigan

Like any good college town, Ann Arbor has a wide-ranging and well-balanced set of recreational activities come summertime, from hiking trails over Ford Lake to water excursions in the Huron River to museum hopping. Then there’s your food and drink itinerary, which, of course, should start at Zingerman’s. The world-famous deli has been drawing patrons for decades for its made-to-order sandwiches—namely the Reuben. Post-lunch, unload your luggage at the Graduate, Ann Arbor’s outpost of the campus-inspired hotel group. Then spend the afternoon outdoors exploring Nichols Arboretum or Gallup Park, and for dinner reserve seats at Spencer, a laid-back locale frequented for plates like harissa lamb flatbread and asparagus tabbouleh. Wrap up the night with a cone at Blank Slate, the town’s trusted fix for all ice cream cravings. (About a four-hour drive)

an old brick house with trees in the background with Shakespeare's Birthplace in the background © Courtesy Deer Path Inn

Lake Forest, Illinois

For a city break within 60 minutes, visit Lake Forest, a luxury retreat boasting sprawling estates, quaint shops, and pristine Lake Michigan views. Get a taste of the town’s storied history at Deer Path Inn, a Tudor-style boutique hotel that opened in 1929 just blocks from the beach. Settle into any of the English-inspired rooms for a wealth of upscale amenities (think Frette linens and bathtubs that fill from the ceiling), and be sure to visit their patio for dinner, where salads, starters, and a full sushi menu await. Come morning, peruse the village market shops and the Lake Forest Book Store, a local gem founded in 1949 by an association of 12 local women. Keep those artistic vibes going with a drive by Ragdale, a nonprofit artists’ residency built in 1897 by architect Howard Van Doren Shaw, then make an afternoon of it at the Chicago Botanic Garden, a 385-acre expanse of gardens and natural terrain. (About a 45-minute drive)

a yellow flower in front of a building © Getty

Iowa City, Iowa

For college town vibes with international intellect, make it a straight shot west on I-80 for Iowa City, home to the University of Iowa and a UNESCO designation as a City of Literature (the only one in the country). Credit that title to the school’s lauded Writers’ Workshop and International Writing Program, which debuted the first creative writing degree in 1936. Stroll the campus, past the buildings that house those artists, then take advantage of the town’s eats. Stop for coffee and croissants at Deluxe, a baked goods haven on the city’s East Side, then head to Rapid Creek for a taste of locally made cider. Finally, check into Hotel Chauncey and opt for rooftop cocktails before a flick at FilmScene, a recently opened art house theater showcasing independent films and special events. (About a three-and-a-half hour drive)

a church with a clock on the side of a road © Eric Fehrenbacher/Getty

Madison, Wisconsin

Home to three lakes, a thriving food scene, and a nationally acclaimed university, Madison is a must-see for any Midwesterner—especially during summer months. Make your first stop Brittingham Boats to take a kayak or stand-up paddle board out on Lake Monona, then explore more than 16 acres of flora at the Olbrich Botanical Gardens. From there, unpack at the Speckled Hen Inn, a small bed and breakfast with big-time charm, or head for downtown digs at the AC Hotel Madison (and straight away to the Eno Vino terrace, for gorgeous views of the Capitol Building). For dinner, stroll a couple of blocks to Graze, a corner fixture from the beloved Tory Miller, for farm-to-table comfort foods like beet burgers and fried local cheese curds, or to Osteria Papavero, for house-made pasta and Italian wine. Before you leave town, pick up some sweet souvenirs at the Madison Chocolate Company, including those filled with curry, rose petals, or—for the brave—ghost pepper. (About a two-and-a-half-hour drive)

a small boat in a large city with Old Courthouse in the background © Getty

St. Louis, Missouri

When a bigger escapade beckons, load up the car and head south for St. Louis. You’ll know you’re there when you spot the Gateway Arch, the 630-foot monument commemorating Thomas Jefferson's Louisiana Purchase and the expansion of the American West. From that sky-high starting point, head under the sea with a trip to the St. Louis Aquarium, just opened in 2019 with 13,000 animals. Tap into the city’s ever-growing beer scene (now up to more than 50 craft breweries), then dine at Elmwood , a New American eatery with an emphasis on charcoal-grilled plates and kitchen-forward cocktails like coffee-washed negronis. Sleep in at the smartly outfitted Chase Park Plaza , and spend Saturday perusing Forest Park and the Central West End before another show stopping dinner at Bulrush, where classic Ozark cuisine reigns (from butter poached walleye to acorn doughnuts). (About a five-hour drive)

a small house in a garden © Alamy

Mineral Point, Wisconsin

Three hours northwest of Chicago you’ll find Mineral Point, a former mining town and the “start of Wisconsin” (where Henry Dodge was inaugurated as the first governor). Today it caters to those seeking history, nature, and the arts, as evidenced by Shake Rag Alley, a nonprofit arts education center spanning several acres of gardens and walking paths. Visit for any of their upcoming programming (an Art Adventure mixed-media retreat in August or a Writers Retreat in September), and consider staying onsite at one of the three private rooms at the Coach House. Outside the center explore local food highlights like sandwiches at Gray Dog or award-winning cheddar at Hook’s, a nationally recognized cheese producer with nearly five decades in the business. Later on, snag a table at Popolo for wood-fired pizzas, or try Tequila Point for south-of-the-border fare. (About a three-hour drive)

a body of water next to the ocean © Alamy

Saugatuck, Michigan

Brimming with arts and culture, seasonal eats, and a relaxing beach scene, this small town a few hours from the Windy City, is one of the best summer getaways from Chicago. Kick off your visit with a stop at Pennyroyal Provisions , an all-day café featuring solid breakfast fixes like blueberry pancakes and challah French toast, then head to Oval Beach. Its soft sand and striking sunsets make it one of the Midwest’s most prized lakefronts. Travel back to town for an afternoon exploring the art galleries lining quaint side streets, then check into your room at the Judson Heath Colonial Inn , an eight-room bed and breakfast brimming with charm and home-away-from-home comforts. When hunger strikes, visit Fennville, 15 minutes away for dinner at Salt of the Earth , a local favorite for freshly baked bread, wood-fired pizza, and a thoughtful wine selection. (About a two-and-a-half-hour drive)

a long bridge over a body of water with a city in the background © Getty

Milwaukee, Wisconsin

Just 90 miles north of Chicago, Milwaukee is so close you could do it as a day trip. But there’s no shortage of options for those looking to stay a while. Try the Iron Horse, a 100-year-old converted warehouse in the town’s bustling Walker’s Point district. Grab snacks at the Yard, their outdoor dining hub, then move on to a beer tasting through town (after all, Schlitz, Pabst, and Miller were all born here). Head to Ristorante Bartolotta dal 1993 , set for an early July opening, for pappardelle with duck ragu from chefs Paul Bartolotta and Juan Urbieta, then make your way to Bryant’s for a Wisconsin-style old fashioned (made with brandy instead of whiskey). Come morning, unwind with a visit to Bradford Beach, one of the city’s favorite lakeside spots for sand and sun. (About an hour-and-a-half-hour drive)

a large waterfall in a forest © Nicola Patterson/Getty

Starved Rock State Park, Illinois

Embrace the great outdoors at this state park , located just 100 miles west of Chicago proper. Situated along the Illinois River, the destination boasts more than 13 miles of hiking trails, waterfalls, and sandstone canyons. Once onsite you’ll find myriad ways to explore: fishing, hiking, and, for those who want a more relaxing visit, trolley tours. Catch views of the Starved Rock Dam at Lover’s Leap Overlook or the Illinois Waterway from Eagle Cliff, then settle into any of the private cabins at Starved Rock Lodge , a woodsy stay surrounded by lush forest trails that’s been taking visitors since the 1930s. (About a 1.5 hour drive)

a view of a city street filled with traffic surrounded by tall buildings © Getty

Detroit, Michigan

Michigan’s largest city has much to offer come summertime. Jump start the weekend with a visit to the Detroit Institute of Arts , where you’ll find Diego Rivera’s Detroit Industry Murals and tens of thousands of other works spread across 100 galleries. Next, explore the serious food and drink scene that has developed over the last decade. Restaurants like Selden Standard , SheWolf , and MAGNET are setting the standard for quality plates in hip environs (with more on the way this year, including Sauce, the California-inspired concept from Heirloom Hospitality ). Close out the day with a visit to Campus Martius Park, where you can find a beach in the middle of downtown Detroit, before turning in at Shinola Hotel , the art-infused boutique hotel from the Detroit-based goods retailer in collaboration with real estate firm Bedrock. (About a 4.5 hour drive)

Gallery: 14 Best Road Trips in America (Condé Nast Traveler)


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