Home>Travel inspiration>Cities We Love

The 10 Best Airbnbs in Chicago to Book Right Now

By Rebecca Holland

Jan 23, 2019

share this article
Book a stay with Airbnb in the Florsheim Mansion, one of the more famous homes in Chicago.

Courtesy of Airbnb

Book a stay with Airbnb in the Florsheim Mansion, one of the more famous homes in Chicago.

Depending on which neighborhood you want to stay in, there are plenty of options to live like a local in the Windy City. Here’s our guide to the city’s top Airbnb rentals.

share this article

Chicago is a big place, but its neighborhoods are so distinct that you could easily spend a whole trip exploring the restaurant-focused West Loop, trendy Logan Square, nature-centric Lincoln Park, or the swanky Gold Coast.

Once you’ve decided on the best base for your tastes, each neighborhood comes packed with inviting Airbnb rentals and friendly hosts offering everything from affordable shared rooms to entire historic mansions. Whether you’re looking for quick-hit accommodations near the airport or want to stay a while in the heart of downtown, we’ve selected 10 of our favorite Airbnb listings to fit any type of Chicago trip.

Posh Gold Coast Stay at the Florsheim Mansion

Book Now: From $604 per night (11 guests), airbnb.com

The Florsheim Mansion—named after shoe heiress Lillian Florsheim—is one of the more famous homes in Chicago. Even if you’re only a bit into architecture, it’ll be a real treat to stay here. Designed by architect Andrew Rebori (and later renovated by Bertrand Goldberg, who added a galley kitchen to join two apartment units), the home’s interior is modern and white, with plenty of colorful accents. Up to 11 guests can spread out over the five-bedroom/five-bath layout; there are also two living areas, a study, an art room, and a large garden. Set on a mansion-lined strip in the Gold Coast neighborhood, this place is only steps from Lake Michigan and the Magnificent Mile. It’s an ideal base for hosting a swanky event or a weekend away with a group of friends.

This stylish stay, set within a renovated former hotel dating to the 1920s, is steps away from Lincoln Park.

Former Historic Hotel in Lincoln Park

Book Now: From $225 per night (5 guests), airbnb.com

Situated within a renovated, former 1920s-era hotel, this apartment is located across from the Lincoln Park Zoo and Lincoln Park Conservatory. The original archways add character, but the unit is modernized with everything you need for a comfortable stay. It has two bedrooms and bathrooms, a full kitchen, washer and dryer, and cheerful decor throughout. Large windows and doors let in loads of natural light. Stock up on kitchen fare at Lincoln Park’s twice-weekly farmers’ market (from May to October); plus it’s a short walk to the neighborhood’s numerous restaurants and boutiques.

English Garden Apartment in Logan Square

Book Now: From $107 per night (4 guests), airbnb.com

Article continues below advertisement

Logan Square might be Chicago’s trendiest neighborhood, with its array of cocktail bars (Scofflaw for gin, Billy Sunday for amaro, Lost Lake for tiki drinks) and vintage shops (Shop 1021 for gifts, Tusk for women’s vintage clothing). Stay in the middle of it all in this cozy greystone that’s next to bustling Logan Boulevard and the historic Logan Theater. The two-bedroom, one-bath apartment has a huge kitchen and is fully furnished with unique pieces and everything you might need throughout your stay. Guests have access to an English garden and are mere steps from the convenient Blue Line train, too. 

Close to Wrigley Field, this spacious home can accommodate up to eight guests.

Kid-Friendly House in Wrigleyville

Book Now: From $600 per night (8 guests), airbnb.com

This huge home is in the center of all the Wrigleyville action, yet is hidden from the street and surprisingly quiet. With four beds, two baths, and an open living area and kitchen, it’s a solid bet for a family or group of friends in town for a Cubs game. You’ll be minutes from the neighborhood’s most popular bars and restaurants, steps from the Red Line train to downtown, and close to Wrigley Field. The family who owns the home has children, so the house is kid-friendly and stocked with games, toys, and even a swing.

Artsy digs await in this shared apartment in Uptown.

Artist’s Haven in Uptown

Book Now: From $66 per night (2 guests), airbnb.com

Stay in a private room in this Uptown apartment and your payment will go toward supporting local artists and homeless youth in the area. The greystone is decorated with rotating works of art and colorful accessories, including original midcentury furniture. (Ask your host for a tour of the art on display from his collection.) The rental is close to the Red Line train, which takes you downtown and is near many live music venues like the Green Mill, a former Al Capone hangout that’s great for jazz. You’ll also find good eateries nearby like Demera Ethiopian Restaurant.

Shared Lodging in Upscale Hyde Park

Book Now: From $55 per night (2 guests), airbnb.com

Stay in a private room (with your own bathroom) in this lovely Hyde Park home. Guests have their own entrance and access to Wi-Fi, the kitchen, and the spacious front lawn. You’ll be located in an upscale area of Hyde Park, near the Obama home and the University of Chicago, as well as the Museum of Science and Industry and Jackson Park. The house is within walking distance to the L and Metra, too, making it easy to get downtown or to the airport.

Guests can rent a private room in a lovely vintage home in Andersonville, on the north side of Chicago.

Cheerful Duplex in Andersonville

Book Now: From $28 per night (2 guests), airbnb.com

Article continues below advertisement

Your private room and bath, in a beautiful vintage home in Andersonville, is close to dozens of local shops, restaurants, and art galleries. The room is bright and minimalist, with a bed, closet, and desk. Guests also have access to the living room and full kitchen. The neighborhood feels a bit removed from the city, but this duplex is right off the Red Line and easily accessible to downtown. It’s a perfect base for an extended stay or for someone hoping to explore a new area of Chicago.

Venture slightly outside of central Chicago to Andersonville for a stay at a castle-like house fit for a king.

Royalty-Ready “Castle” in Andersonville

Book Now: From $129 per night (4 guests), airbnb.com

Make way for the historically Swedish Andersonville neighborhood on the north side of Chicago, where you can live like royalty in this castle-styled home stuffed with baroque and rococo antiques. Wake up to the sun streaming through stained glass windows, relax in the ornate sitting room, try your hand at the antique piano, or take your time getting ready in the crest-clad marble bathroom. The home, which is listed on the National Register of Historic Places, features a sculpture garden and full kitchen, as well as a living room, dining room, study, and two bedrooms.

Urban Retreat in West Loop

Book Now: From $139 per night (4 guests), airbnb.com

Stay in this large studio in West Loop for skyline views and walking-distance access to some of Chicago’s most-buzzed-about restaurants and bars. Seriously spacious, the studio sleeps four guests between a bed and a sofa bed. There’s also a decent-sized kitchen and full bathroom; the balcony boasts views over the Chicago skyline. West Loop is packed with some of Chicago’s best restaurants along Restaurant Row, innovative cocktail bars like The Aviary, and numerous art galleries and high-end boutiques, many of which are housed in former warehouses.

Bunk down in this no-frills but clean and affordable home set within minutes of Chicago O’Hare.

Convenient Budget Stay Near O’Hare

Book Now: From $52 per night (1 guest), airbnb.com

If you’re on a long layover or in town for an event near O’Hare International Airport, this convenient and affordable rental is worth a look. Opt in for either a shared or private room; it’s no-frills, yes, but clean and run by a responsive host. Plus, you can check yourself in, so it doesn’t matter what time your flight arrives. The house is a seven-minute drive from O’Hare and near a pizza spot, taco restaurant, and American grill, when it comes time to refuel.

>> Next: 10 Best Road Trips From Chicago for a Weekend Getaway

Products we write about are independently vetted and recommended by our editors. AFAR may earn a commission if you buy through our links, which helps support our independent publication.

Sign up for the Daily Wander newsletter for expert travel inspiration and tips

Please enter a valid email address.

Read our privacy policy