Best Weekend Getaways From Chicago

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Chicagoans itching to travel right now should not underestimate the power of a great winter road trip, and not just because it may feel like the only safe option at the moment. In a break from the norm, we’ve found exciting places offering something fresh and surprising for the Midwest, making them well worth the drive. A fun, elegant cocktail experience, lakefront retreats that offer stunning views, snowy ski trips with plenty more to do off the slopes—it’s all available. Here are the best weekend getaways from Chicago.

(Editors note: Given the changing nature of the COVID-19 pandemic, the hours and accessibility of many venues are fluid and subject to change. Make sure to contact them before visiting.)

All listings featured on Condé Nast Traveler are independently selected by our editors. If you book something through our links, we may earn an affiliate commission.


Distance from Chicago 33 miles

What to Do

In less than 60 minutes by Metra or just over 30 minutes by car, find yourself feeling far from the city in this pretty Northshore town off of Lake Michigan. No doubt Lake Forest is fancy with its sprawling estates, Market Square, and upscale shops (check out the all-women-run Lake Forest Bookstore and Valentina boutique), and coveted waterfront views. Being here also puts you 20 minutes closer to the 385-acre Chicago Botanic Gardens, where the Japanese and dwarf confider gardens are especially sublime in winter.

Where to Stay

The main reason to go to Lake Forest now is a weekend away at the 57-room Deer Path Inn (from $329 per night), a fabulous, little-known gem that puts you in arm’s reach of the shops and lake, and offers many experiences available only to guests. Opened in 1929 with the style of an authentic manor house, the elegant inn feels as storied and local as it does far-flung and English. Spacious, modern, and sophisticated rooms offer upscale amenities (think Frette linens and bathtubs that fill from the ceiling); recently, the inn began in-room delivery of its popular Afternoon Tea service, complete with a tower of tea sandwiches, petit fours, and tartelettes. Patio dining in the English Garden at Deer Path is scenic and doable in winter with heaters. Guests at the hotel can also reserve the inn’s hidden cellar for a new, private, and totally custom cocktail or wine tasting paired with dinner that’s led by Deer Path’s fun and expert chief spirits officer, Jorge Centeno.


Distance from Chicago 49 miles

What to Do

Drive just 60 minutes and find yourself surrounded by beauty in the 15,000-acre Indiana Dunes National Park, which packs in an astounding amount of botanical diversity thanks to its variety of lowlands, highlands, prairies, wetlands, forests, and Lake Michigan shoreline. Time your visit with cool winter conditions, when snow cloaks the park in white, and there’s a chance to see spectacular shelf ice formations on the water, not to mention you’ll get a far more secluded experience. Venture out on cross-country skis or snowshoes—the latter of which can be borrowed for free at the park’s Paul H. Douglas Center for Environmental Education. All of the park’s 50 miles of trails are available for winter activities, but opt for a one-mile loop or three-mile route on the Paul H. Douglas Trail, which takes you to the beach through a rolling black savannah, one of the rarest habitats in the country. Often confused with the national park, the two-acre Indiana Dunes State Park, immediately next door, is also open and admission is waived on weekdays in winter.

Where to Stay

Nearby Chesterton offers a good location central to both parks, and interesting B&B’s are the way to go. Within walking distance to restaurants and shopping, Riley’s Railhouse Bed & Breakfast (from $140 a night) is housed in a former New York Central style freight station and has rooms in real rail cars. The family-friendly DunesWalk Inn at the Furness Mansion (from $125 a night—you can also rent the entire place out on Airbnb) is another historic option that balances digs in an 1881 mansion with modern comfort, just a few minutes from the beach.


Distance from Chicago 75 miles

What to Do

Didn’t score a Michigan beach house last summer? Winter isn’t hot, but it’s a gorgeous and secluded time to experience the dramatic Lake Michigan coast from the comfort of a luxury beach home, most of which can be had now at low season rates. Take your pick of towns on the state’s south coast like Union Pier, New Buffalo, and little-known Harbert. Sans summer crowds, this is the time to stop at the harborside Stray Dog Bar & Grill. Even better, book an igloo for outdoor dining at small-batch Beer Church Brewing, try alfresco wine tastings at Round Barn Estate, or get takeout from Red Arrow Roadhouse (try the buffalo cauliflower and nachos) and locally made whiskey from the Journeyman Distillery to bring back home. As everyone does, give into the pull of the lovely Lake Michigan coast, where dune walks and sledding at Warren Dunes State Park should be high on your list.

Where to Stay

Bluefish Vacation Rentals (from $100 a night) is your best option for a well-curated assortment of homes throughout Harbor Country, plus the bonus concierge-like guidance of the local husband-and-wife team who run it, Jason and Erika Milovich. In winter, most of their homes can be had at low season rates and don’t require summer’s usual full week stay. The scenery can’t be beat in Harbert at three-bedroom Water’s Edge, a splurge-worthy find tucked into a forested bluff overlooking a private stretch of Lake Michigan shoreline; spend $750 a night in winter verses the nearly double rate of $1,429 a night in summer. Walk the beach and watch glacier-like ice form with the waves, warm up in the hot tub, and light a bonfire under starry winter skies framed by trees. Other notable options include the three-bedroom Harbor Time, new five-bedroom Darby Cottage with its massive showroom-worthy open kitchen, and new four-bedroom Lake Life that puts spectacular lake views right in your lap.


Distance from Chicago 149 miles

What to Do

On a drive of just over two hours, cruise past Mars Cheese Castle in Kenosha (hit the brakes to load up on Wisconsin gold), and lakefront Milwaukee, on your way to Kohler. Popular in temperate months for its jaw-dropping golf courses, which regularly feature on the PGA Tour, Destination Kohler is a find in winter with fewer visitors, killer spa treatments at its Kohler Waters Spa, and invigorating outdoor adventures at its lesser-known River Wildlife preserve. Like Kohler’s golf courses, the 500-acre wilderness playground showcases the natural beauty of the landscape here. Try hikes and horseback rides through rolling trails, ice skating and curling at Winter Wonderland, guided trap shooting in a forest canyon, and brunch or hot toddies at River Wildlife Lodge, the preserve’s atmospheric log cabin outpost.

Where to Stay

Options at the resort include classic hotel rooms at the 241-room American Club (from $189), but four chic and splurge-worthy cabins (from $842 a night) are the way to go, especially if you want privacy and space wrapped in some gorgeous nature. The two-bedroom Lake Cabin (from $1009 a night)—one of two opened just last summer—positions you on a staggering bluff just above Lake Michigan. The beach is inaccessible from this rugged perch, but you won’t care with endless, ocean-like views from the back porch and firepit, and the sprawling evergreen forest at the front of the house that doubles as a wildlife crossing (watch for deer and wild turkeys). It’s all the more magical with a dusting of snow on the beach grass, a warm fire, and dinners inside your own beautiful kitchen—everything from tenderloin and ricotta gnocchi takeout from the new Taverne on Woodlake to whiskey pairings, curated Wisconsin cheese boards, and gourmet groceries delivered from Woodlake Market.


Distance from Chicago 164 miles

What to Do

With rolling forested landscapes, an historic downtown on the Mississippi River, and the best (one of the only!) ski mountain in Illinois, Galena is as charming as ever in winter. Even the two-hour-and-45-minute drive sets the mood as flat highways turn to one-lane roads that climb gentle hills and weave through farmlands and woods, eventually dropping you into this once-thriving river port town. Stroll the downtown’s Main Street for a superb array of local shops and studios; new options include Galena Book & Paper, the Galena Spoon Company for handcrafted spoons and carving classes, and Scent Workshop, where you can learn French perfuming techniques. There are loads of restaurants and boozy options here, too; go for especially good take-home dining and cocktail kits from French-meets-German Fritz and Frites, Miss Kitty’s Grape Escape, and the drive-thru Galena Brewing Co. Downhill skiers won’t want to miss Chestnut Mountain Resort, just 15 minutes from the downtown, with 19 runs that race to a halt at the bank of the Mississippi River.

Where to Stay

It’s a-okay to vape in the new guest-only “potting shed” outside the pretty five-bedroom Aldrich House, Illinois’ only cannabis-friendly bed and breakfast (from $145 a night). For something upscale and romantic, it’s hard to do better than the luxury six-suite Jail Hill Inn, set in a former jailhouse at the end of Main Street and serving a three-course breakfast (from $345 a night). Families settle in nicely at the stylish, condo-like Ulysses Suites (from $214 a night), while south of downtown on 6,800 acres of Galena Territory, Eagle Ridge Resort & Spa offers a robust nordic activities program and everything from simple hotel rooms to full homes (from $99 a night).


Distance from Chicago 185 miles

What to Do

Every worthwhile weekend getaway from Chicago isn’t a charming small town or lakeside retreat. For those who want some city culture that isn’t their own, Indy’s Bottlework’s District is calling. Stop in Merrillville for proper road trip junk food—fresh Indiana-made gummy bears—at Alabanese Confectionery Group on the three-hour drive south to Indy. Once there, head to the new 12-acre, mixed-use neighborhood that spans the north side of Mass Ave in downtown Indianapolis and brims with local indie shops in historic industrial buildings. Explore the mix of offerings at Circle City Industrial Complex, a 500,000 square-foot warehouse opened in the old Schwitzer car manufacturing facility, where you should check out newly opened SoChatti dairy-free chocolate tasting room and a class at Indy Fused Glass. Other new places worth a visit are Good Neighbor for fresh duds and the Living Room movie theater. For dinner, head out of the district for romantic outdoor dining in the new fireside greenhouse huts at Public Greens, a modern, community-driven restaurant that shares its profits to feed nearly 2,000 of Indy’s less fortunate youth every week.

Where to Stay

Opened in December in what was formerly the world’s largest Coca Cola bottling plant, the 139-room Bottleworks Hotel (from $249 a night) is the stylish new anchor for the Bottleworks District. The industrial, art-deco-inspired hotel occupies the top two floors of the historic building, showing off a white terra-cotta exterior and brass-patterned doors. High-style rooms have velvet couches, loft ceilings, and terrazzo-tiled floors. Adjacent to the hotel, find more dining options at Garage Food Hall, Indy’s first food hall opened this month in the factory’s former garages, with nearly two dozen vendors serving everything from lobster rolls and poke to Pakistani-Indian fare and Brazilian steak.


Distance from Chicago 346 miles

What to Do

Make your winter ski trip happen at Boyne Mountain Resort, one of the most exciting ski mountains within a reasonable drive of Chicago—five and a half hours, plus a one-hour time change. Rising up from the northern part of Michigan’s lower peninsula, the mountain offers 500 feet of vertical with 60 downhill trails for a range of skiers and riders, though the biggest perk of a visit here is the abundance of high-quality outdoor adventures that go beyond skiing. Rent a new sno-go ski bike and shred downhill runs, fat-tire bike on forest trails, zipline 50 feet in the air across the mountain, cross country ski or snowshoe on dedicated trails, ice skate or snow tube, and even dine outdoors in one of five igloos serving at Forty Acres Tavern. If you have a little extra time you can also tack on the 40-minute drive north to Boyne Highlands, the mountain’s sister resort, for even more challenging ski terrain plus the new “Enchanted Trail,” an illuminated two-mile trail for nighttime winter walks and snowshoeing. NOTE: Like other ski resorts around the country, both mountains are limiting capacity during the pandemic and booking lift tickets and gear rental in advance is recommended.

Where to Stay

Spread out in one of the fully-equipped three- and four-bedroom Mountain Cabins that are part of the resort (from $607 per night). Each set in the woods with a hot tub on the deck, fully equipped for cooking your own meals, and offers ski-in/ski-out access . Some of the cozy one- and two-bedroom condos at the Village at Disciples Ridge also offer ski-in/ski-out access (from $488 per night). Pro tip: the best way to guarantee access to the slopes this season along with your accommodations is to book a “Ski & Stay Package,” which bundles lodging and lift together and lets you ski both resorts.

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