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Search results; Over 1,000 places

Flat in Streeterville
3B Luxury Penthouse w/ Sweeping Views, Pool & Gym
3 beds
21–26 Apr
New place to stay
Superhost
Flat in The Loop
Comfy 2BR-2BTH, Ideally Located!
3 beds
21–26 Apr
New place to stay
Guest favourite
Flat in Streeterville
2br/2ba, A+ location by Mag mile, views & spacious
4 beds
5–10 May
4.94 out of 5 average rating, 257 reviews
Hotel in The Loop
Multipurpose work station and ultra-fast WiFi
1 queen bed
21–26 Apr
New place to stay
Superhost
Flat in The Loop
Luxury Corner 2 Bedroom in the Loop | Roof Deck
3 beds
30 Jun – 5 Jul
4.77 out of 5 average rating, 201 reviews
Hotel in River North
Playful spirit and sustainable practices
1 queen bed
18–23 Apr
4.5 out of 5 average rating, 160 reviews
Superhost
Place to stay in River North
Chicago Speakeasy-Style Loft (Room 2B)
2 beds
21–26 Oct
4.89 out of 5 average rating, 114 reviews
Superhost
Flat in The Loop
Millennium Park Getaway (2BD)
3 beds
20–25 May
4.59 out of 5 average rating, 70 reviews
Superhost
Flat in The Loop
Cloud9-Indoor Pool, Gym, Rooftop-The Tulip
4 beds
18–23 Apr
New place to stay
Flat in Near North Side
The Bulls' Nest: The Chicago Retreat
22–27 Apr
New place to stay
Superhost
Flat in The Loop
Cozy 2BR-2BA steps from 'The Bean' & Michigan Ave
20–25 Apr
4.9 out of 5 average rating, 136 reviews
Superhost
Flat in Magnificent Mile
Urban Chic Apartment by the Magnificent Mile
2 queen beds
23–28 Oct
4.94 out of 5 average rating, 213 reviews
Superhost
Home in Near North Side
503LOFT | Top Floor 5 BED, 2 BA Downtown Loft
3 beds
26–31 May
4.85 out of 5 average rating, 81 reviews
Superhost
Flat in The Loop
Spacious & Stylish 2BR-2BA Apt Steps from The Bean
4 queen beds
21–26 Apr
4.79 out of 5 average rating, 138 reviews
Superhost
Flat in The Loop
Modern 3BR Penthouse in the Loop | Roof Deck
4 beds
21–26 Apr
4.66 out of 5 average rating, 179 reviews
Guest favourite
Flat in Near North Side
201LOFT | 5 BED, 2.5 BA Downtown Spacious Loft
6 beds
23–28 Jun
4.95 out of 5 average rating, 43 reviews
Flat in Near North Side
Downtown Riverwalk Music Inspired Loft
3 beds
21–26 Apr
4.73 out of 5 average rating, 44 reviews
Flat in Streeterville
Guest 2 Queen Room at Aloft Chicago Mag Mile
2 queen beds
18–23 Apr
New place to stay