Over 1,000 places

Guest favorite
Hotel in The Loop
Relaxing Getaway in Chicago w/ View, Pets Welcome!
2 queen beds
Apr 19 – 24
5.0 out of 5 average rating, 6 reviews
Superhost
Apartment in The Loop
Comfy 2BR-2BTH, Ideally Located!
3 beds
Apr 21 – 26
New place to stay
Guest favorite
Apartment in Streeterville
Lake, City, & River View Condo
Apr 19 – 24
5.0 out of 5 average rating, 9 reviews
Apartment in Near North Side
The Bulls' Nest: The Chicago Retreat
Apr 22 – 27
New place to stay
Guest favorite
Place to stay in River North
Chicago Speakeasy-Style Loft Space (Room 1A)
2 beds
Sep 1 – 6
4.9 out of 5 average rating, 535 reviews
Superhost
Apartment in The Loop
Luxury Corner 2 Bedroom in the Loop | Roof Deck
3 beds
Jun 30 – Jul 5
4.76 out of 5 average rating, 202 reviews
Superhost
Apartment in The Loop
Cozy 2BR-2BA steps from 'The Bean' & Michigan Ave
Apr 20 – 25
4.9 out of 5 average rating, 136 reviews
Superhost
Home in Near North Side
503LOFT | Top Floor 5 BED, 2 BA Downtown Loft
3 beds
May 26 – 31
4.85 out of 5 average rating, 81 reviews
Guest favorite
Apartment in Near North Side
53 Floor MagMile Penthouse Views, Balcony, Pool
3 beds
Apr 20 – 25
4.97 out of 5 average rating, 31 reviews
Superhost
Apartment in Magnificent Mile
Urban Chic Apartment by the Magnificent Mile
2 queen beds
Oct 23 – 28
4.94 out of 5 average rating, 213 reviews
Guest favorite
Apartment in Near North Side
201LOFT | 5 BED, 2.5 BA Downtown Spacious Loft
6 beds
Jun 23 – 28
4.95 out of 5 average rating, 44 reviews
Superhost
Apartment in The Loop
Spacious & Stylish 2BR-2BA Apt Steps from The Bean
4 queen beds
Apr 21 – 26
4.79 out of 5 average rating, 138 reviews
Superhost
Apartment in The Loop
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
2 queen beds
May 9 – 14
4.78 out of 5 average rating, 155 reviews
Guest favorite
Apartment in The Loop
Bright 2BR-2BA steps from The Bean & Michigan Ave
2 beds
Aug 4 – 9
4.91 out of 5 average rating, 107 reviews
Guest favorite
Apartment in Magnificent Mile
Chic 2BR Gem with Fireplace
2 beds
Jul 8 – 13
5.0 out of 5 average rating, 19 reviews
Superhost
Apartment in The Loop
Millennium Park Getaway (2BD)
3 beds
May 20 – 25
4.59 out of 5 average rating, 71 reviews
Apartment in Streeterville
3B Luxury Penthouse w/ Sweeping Views, Pool & Gym
3 beds
Apr 21 – 26
New place to stay
Apartment in Near North Side
Downtown Music Loft
3 beds
Oct 15 – 20