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7 Coolest Airbnb Rentals in Chicago

Chicago is home to some of the best hotels in the United States. But to get a more local perspective and get to know the city’s diverse neighborhoods a bit better, you can stay in a local Airbnb as a hotel alternative. There are lots of great Airbnbs to choose from in Chicago, including private rooms, entire apartments, and even sailboats! Here are some of the coolest Airbnbs in Chicago to choose from.

Industrial Style Chicago Loft Living room at Industrial Style Chicago Loft with Free Parking
Credit: Living room at Industrial Style Chicago Loft with Free Parking by airbnb.com

Industrial Style Chicago Loft

This industrial-style loft on Airbnb is great for two guests. You’ll have the whole loft to yourself with one bedroom and one bathroom. This is a chic place to stay with a California king-size bed, Netflix, an art deco ceiling, and free parking. You’ll have a full kitchen with stainless steel appliances, complimentary toiletries and towels, and an outdoor deck to use as you like. It’s spotlessly cleaned after each use, and luggage drop-off and storage is available as a courtesy at the restaurant downstairs.

Hip Chicago Apartment Hip Chicago Apartment
Credit: Hip Chicago Apartment by airbnb.com

Hip Chicago Apartment

It’s fun to be in the hip Logan Square neighborhood when you visit Chicago and stay in this condo that suits up to four guests. It has two bedrooms and one bathroom and is a stylish place to relax and enjoy the local vibe. Perks include free parking, washer and dryer, TV, Wi-Fi, bathroom essentials, and access to a diverse array of bars, restaurants, and green spaces.

Urban Farm Fun Urban Farm Airbnb
Credit: Urban Farm Airbnb by airbnb.com

Urban Farm Fun

For something entirely different that you might not expect in Chicago, consider staying at Nicky’s urban farm apartment. You’ll have the entire apartment to yourself for up to five guests. It’s located on the West Side of the city and is an actual organic farm with chickens, goats, pigs, and bees. You’ll be just a 10-minute train ride from downtown via the CTA Green Line. This is a clean and cozy garden unit apartment that has free laundry facilities, free Wi-Fi, access to the grill and smoker, and occasionally even access to bikes and a car to get around.

Apartment with Great Location & Free Parking Seating at Apartment - Great location. Free parking
Credit: Seating at Apartment - Great location. Free parking by Airbnb.com

Apartment with Great Location & Free Parking

You can stay at this apartment to be in the Wicker Park/Bucktown area and enjoy all that this location has to offer. It’s just a block from the Division blue line stop. Two guests can stay here and use the bedroom with a queen-size bed, bathroom, internet, central heat and A/C, small fridge, and microwave. There is free private parking here, as well as a small safe, coffeemaker, and DVD/Blue Ray player.

Humboldt Park House Apartment Exterior of Humboldt Park House
Credit: Exterior of Humboldt Park House by Airbnb.com

Humboldt Park House Apartment

Experience the historic Humboldt Park neighborhood when you book this Airbnb rental on the Near Northwest side. The space is a 600-square-foot row house single unit on the first floor that dates back to 1896. It sleeps up to five people and has two bedrooms and one bath. Guests have access to the whole apartment and also the porch, deck, and laundry area in the basement upon request. It’s an ideal space for two couples, a group of friends, or a solo traveler looking for a relaxing staycation to work or explore the area.

Private Studio in Bridgeport Private Studio in Bridgeport
Credit: Private Studio in Bridgeport by airbnb.com

Private Studio in Bridgeport

An affordable place to stay in the diverse Bridgeport neighborhood is this studio guesthouse for up to three people. It is a place for adults but not children or pets. You’ll get a kitchen with a mini-fridge, microwave, sink, and Keurig, as well as dishes and glassware to use. To sleep, there’s a full-size Murphy bed and a couch for a third person. The studio is a detached unit on the back of the host’s property, so you’ll get plenty of privacy here. Laundry machines are available in the main house and can be used by making an appointment. Other offerings of this Chicago Airbnb are Wi-Fi, board games, books, closet space for storage, a portable A/C, ceiling fan, and access to a shared yard. There is a friendly dog that lives onsite.

Egyptian Room - King Bed, 1 Block from CTA Train Dining area at Egyptian Room Airbnb
Credit: Dining area at Egyptian Room Airbnb by airbnb.com

Egyptian Room - King Bed, 1 Block from CTA Train

Another popular and affordable Airbnb to stay at in Chicago is Ryan’s Egyptian room for up to two guests. It’s a private room in a house with one bedroom and 2.5 shared baths. Unmetered street parking is easy, there’s a full kitchen, laundry machines available, and public transit a block away. This is a historic limestone/brick mansion from around 1895 and full of character by the Kedzie Green Line train.

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