The Best Airbnbs for Winter Adventuring in Chicago

Chilly snow-globe temps are nearly here and there’s plenty to do in the city to celebrate. Whether you’re interested in checking out one of Chicago’s world-class museums, seeing the ice form on Lake Michigan, or eating your weight in hot deep-dish pizza, you’ll need a cozy base camp to rest your head. Opportunely, a wide variety of Airbnb rentals exist, verified for quality and design, perfect for wintery experiences in the Windy City. Whether you’re a family of two or twelve, dress warm, bring your sense of adventure, and stay in one of these unique and fun urban rentals.


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Host Dinner at a Radiant Home with a Spacious Roof Patio

Airbnb

Neutral colors, gorgeous dark wood floors, diverse art, and interesting design features are what you can expect with a stay in this two-bedroom Forest Park home. Gather for cocktails on the roof patio and enjoy the neighborhood views. Curl up by the fireplace with a glass of wine or hot chocolate. There’s a special event space on the first floor for larger gatherings, perfect for inviting the grandparents over. This is the idyllic locale for hunkering down during a Chicago winter, with your extended family in tow.

Sleeps: 5
Costs: $540/night
Online: Airbnb.com

The Roscoe House near Wrigley Field

Airbnb

If you’ve ever wanted to stay in an updated Victorian, full of style and panache, then now’s your chance with this family-friendly Chicago rental, located within walking distance to many of Chicago’s fabulous restaurants and boutique shops. Colorful art, exposed ductwork, a library, a record player, interesting doorways, a fully stocked kitchen, and a cozy outdoor patio are what you can expect to enjoy during your stay at this light and bright well-located home. Gather around the table for a board game or dress up in layers to explore all that the city has to offer during the winter season. Whatever you do, snap pics under the Wrigley Field marquee and wander over to Gallagher Way for the Christkindlmarket Wrigleyville, ice skating, and street food.

Sleeps: 8
Costs: $540/night
Online: Airbnb.com

Cool & Modern Chicago Apartment near Transit

Airbnb

Well priced, this charming Windy City apartment is a little green oasis tucked into a brick building, located near public transportation, and just three blocks from Horner Park, in the Irving Park neighborhood. The black and white interior gives the space a modern and fresh appeal. You’ll want to snap photos of your kids enjoying hot cider at the kitchen table, with a floor-to-ceiling green wall as a backdrop.

Sleeps: 5
Costs: $149/night
Online: Airbnb.com

Whole Flat in Private Club with Pool. Walk to L, Dining & Shows

Airbnb

Located between Broadway and Lawrence, near public transportation and Lake Michigan, this flat, inside the newly restored Lawrence House, is an ideal location for concert lovers, dining enthusiasts, and shoppers. Enjoy the rooftop deck, with sparkling skyline views, the fitness center, with an old-school boxing gym, and a coveted indoor swimming pool. It’s the public spaces that really shine at this well-reviewed Chicago rental.

Sleeps: 4
Costs: $101/night
Online: Airbnb.com

Unwind in the Bath at a Hip, Historic Coach House

Airbnb

The pops of color bring this Humboldt Park rental to life. Your kiddo will love visiting Humboldt Park, the wintry beach, and the National Museum of Puerto Rican Art and Culture. Hop on nearby public transportation and visit Wicker Park or Bucktown, an easy bus or train ride away. This snug studio has everything you need, and nothing that you don’t. What was once a machine shop is now a well-designed and well-reviewed airy rental.

Sleeps: 2
Costs: $125/night
Online: Airbnb.com

Sunny, Modern Lincoln Park Apartment with Deck

Airbnb

If you’re looking for a rental that just screams “Chicago”, then this two-bedroom, one-bathroom condo is for you. Ideal for a family of four, this Lincoln Park home has interesting design features like wooden-paneled accent walls, Chicago-themed art, and modern furniture situated on a large outdoor deck. The Michelin-rated restaurant, Alina, is nearby as is DePaul University, Chicago History Museum, Lincoln Park Conservatory, Lincoln Park Zoo, Oz Park and the Old Town Triangle. You’ll find that there’s plenty to do in the area to entertain your whole family during the winter season.

Sleeps: 5
Costs: $217/night
Online: Airbnb.com

Charming, Sunny Apartment with Backyard Garden

Airbnb

This private, first-floor rental in Evanston, full of art and unique design features, is ideal for extended stays, for larger families, due to its comfort and style—you’ll feel like you’re in a real home throughout your stay. With three bedrooms and three full bathrooms, your family can stretch out while inside this winter. And, when you’re ready to venture outdoors, in the snow and sleet, you’ll be within walking distance to downtown Evanston’s shops, dining, and green spaces.

Sleeps: 6
Costs: $120/night
Online: Airbnb.com

Eclectic ArtistDesigned Sanctuary Heart of Pilsen

Airbnb

Pilsen is one of Chicago’s most dynamic and vibrant neighborhoods and this condo, located right in the heart of the community, is a true treasure. Inimitable art, colorful accents, brightly colored walls and window treatments, and a great location makes this Airbnb one for the books. The Superhosts are both adventurers and artists, which influences the design choices of the rental.

Sleeps: 4
Costs: $109/night
Online: Airbnb.com

Soak Up Mid-Century Style in Wrigleyville & Boystown

Airbnb

Location, location, location. This Mid-century townhome is located right in the middle of all the action, which means you can enjoy visiting the home of the Cubs at Wrigley, make a dinner reservation at an award-winning restaurant in Boystown, or leave the kids with a sitter and dance the night away in one of the many bars or clubs. With a full kitchen, three bedrooms, three full bathrooms (as well as a half bath), and plenty of outdoor space, however, you might not want to leave your cozy digs at all. 

Sleeps: 12
Costs: $579/night
Online: Airbnb.com

Feel at Home in Chicago, with Parking, Steps from Evanston

Airbnb

A bright gem, located in West Ridge, this city condo has a large kitchen, comfortable living space, and a carport for your vehicle. Or hop on the Red Line and you’ll easily be able to reach downtown Chicago and many of the city’s popular neighborhoods. This family-friendly neighborhood, full of condos and self-contained homes, is ideal for those looking for a classic Chicago neighborhood experience this winter.

Sleeps: 6
Costs: $164/night
Online: Airbnb.com

 — Wendy Altschuler

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