The 6 Best Airbnbs in Chicago, Illinois

Pure elegance awaits at this renovated 1920s former hotel, conveniently located across from the Lincoln Park Zoo and Conservatory. Featuring original Art Deco details including large archways, the space has been largely modernized to offer all the creature comforts needed for a cozy-chic stay. Offering two bedrooms and two bathrooms, it sleeps up to five guests. A full-time rental, this coveted spot offers plenty of options on dates and is available to book all year round.

A hugely sought-after spot in bustling Wrigleyville, this 1894 red-brick coach house is full of surprises. Set back from the street, it’s a little rustic oasis, and has recently been renovated with plenty of contemporary features. Ideal for families thanks to its attention to detail, there are plenty of neat details the kids will love, including a secret play space and a walk-in toy closet. With its prime location near to Wrigley Field, the park, zoo and beaches, this Airbnb is a solid family vacation option.

More than just a loft space, this River West space is just the pad if you’re looking for a place to unwind, hang out and enjoy some quality time with friends or family. A surround-sound cinema room, Jacuzzi and pool table add to its appeal, along with cool hanging chairs and an inviting industrial-retro aesthetic. Sleeping up to eight guests split across four bedrooms, and with three bathrooms, this is luxury lofting at its finest. And while it is tempting to just stay in the space and chill, there are plenty of amenities and attractions within walking distance in the nearby Wicker Park and Bucktown neighborhoods.

Airbnbs don’t come more special than the historic Florsheim Mansion. One of Chicago’s most architecturally significant homes, named after Lillian Florsheim – the shoe empire heir who was a sculptor and renowned gala host – a stay here is a mingling of luxury and history. This legendary spot in the Gold Coast is split into the main house and guest house, which altogether sleep 12 people in five beautiful bedrooms. Expect all the finesse and polish that come with a mansion, including a Steinway grand piano and a formal dining room. There’s also scope to entertain in the property and host events, art performances or large gatherings. And if it’s a little outdoors R&R time you’re after, there’s a Zen garden complete with koi and turtle pond.

With its out-of-this-world vibes and historic flamboyance, the Castle on Berwyn is anything but conventional. It’s utterly luxurious and comes loaded with every kind of antique imaginable. Eccentric through and through, it’s one of Andersonville’s top properties. Touting itself as a Game of Thrones castle-inspired getaway, there is intrigue and opulence in every room. You’ll certainly live like royalty if you book here, but thankfully there are plenty of modern amenities too, including a contemporary kitchen and all mod cons. Sleeping four guests between two bedrooms, it’s both cozy and impressive.

A pad in which pampering comes as standard, this luxury condo features its very own sauna and heated floors to make your stay relaxing. With all new renovations and fixtures, it is super-clean, contemporary and comfortable. Located in the bustling Andersonville neighborhood, it sleeps up to nine guests, with three bedrooms and two bathrooms.