Top
  >  United States   >  Midwest U.S. Airbnbs   >  The Coolest Airbnbs In Chicago
Airbnbs in Chicago

Airbnbs are one of my favorite accommodations, especially for road trips! While hotels are the default accommodation for large cities like Chicago, Airbnbs offer a way for you to experience the city more authentically.

Discover the Best Airbnbs in the Midwest U.S.

Many of the Airbnbs in this post come with superior amenities and more space than hotel rooms. And just because you’re in an Airbnb doesn’t mean you have to compromise on any of the luxuries you might want.

So here are the coolest Airbnbs in Chicago!
page-divider-blue
Airbnbs in Chicago
Airbnbs in Chicago
Whiting, Indiana
4 guests2 bedrooms2 beds2 baths

Okay, so this property is south of Chicago, barely over the state line into Indiana. But the singular beauty and intrigue of this property earned it a place on this list. This home is over 4000 sq ft with two bedrooms, two bathrooms, a dining area, a kitchen, theater/TV area, a music area, an art studio, and a living room. Plus, you can walk to the beach and Lake Michigan.

page-divider-blue
Airbnbs in Chicago
Airbnbs in Chicago
Airbnbs in Chicago
River West Neighborhood
8 guests3 bedrooms4 beds3 baths

Highlights of this property are a movie screening room with a surround sound system and an industrial-chic chef’s kitchen. This loft is a short walk from Wicker Park and Buck Town, is a two-minute walk to the bus and subway, and is in a neighborhood with lots of shops, restaurants, and bars.

page-divider-blue
Airbnbs in Chicago
Airbnbs in Chicago
Wicker Park Neighborhood
2 guests1 bedroom1 bed2 baths

Welcome to your urban oasis! Prepare meals in a spectacular professional-grade kitchen. Relax in a one-of-a-kind former warehouse in one of Chicago’s trendiest neighborhoods. And end your day in the Japanese soaking tub.

page-divider-blue
Airbnbs in Chicago
Airbnbs in Chicago
Airbnbs in Chicago
Irving Park Neighborhood
6 guests3 bedrooms3 beds1 bath

This apartment is plush, chic, minimalistic, and integrates nature into every corner of every room. Your furry friends are welcome to stay with you here. Plus, you’re close to public transportation, shops, restaurants, and nightlife.

page-divider-blue
Airbnbs in Chicago
Airbnbs in Chicago
Old Town Neighborhood
16 guests · 5 bedrooms · 8 beds · 4 baths

This stunning 4000 sq ft penthouse is in the heart of downtown. The property has two units connected by a private staircase. So you’ll have two living rooms, two kitchens, and two laundry rooms. Your pets are welcome here, and as fantastic as the house is, it’s the rooftop terrace you’re not going to want to leave!

page-divider-blue
Airbnbs in Chicago
Airbnbs in Chicago
Airbnbs in Chicago
Near Humboldt Park
2 guestsStudio1 bed1 bath

This is one of the most spacious studio apartments you’ll ever stay in. The high ceilings, eclectic decorations, and industrial ambiance make for a luxurious and unique stay. And the lush, private yard and hot tub provide you with an outdoor oasis.

page-divider-blue
Airbnbs in Chicago
Airbnbs in Chicago
Near Navy Pier
6 guests2 bedrooms2 beds2 baths

The floor to ceiling windows in this high rise apartment make you feel like you’re on top of the world. You can see Lake Michigan from this property’s patio, and you’re a short walk from Michigan Avenue and Millennium Park.

page-divider-blue
Airbnbs in Chicago
Airbnbs in Chicago
Airbnbs in Chicago
Near Avondale and Wicker Park
2 guestsStudio1 bed1 bathroom

Sometimes simple can be the best kind of luxury. This modern, classy apartment packs a big punch of color, art, and historic charm. Plus, the property includes a cozy rooftop deck.

page-divider-blue
Shop My Travel Essentials
page-divider-blue
What are your favorite Airbnbs in Chicago? Tell me in the comments below!
page-divider-blue
For Planning The Rest Of Your Midwest U.S. Trip
page-divider-blue

This article about the best Airbnbs in Chicago is not a sponsored post, and the thoughts and opinions expressed in this post are entirely my own. Some of the links in this post about the best Airbnbs in Chicago are affiliate links, and, at no cost to you, I may earn a small commission.

post a comment