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Search results; Over 1,000 places

Hotel in The Loop
Comfy queen for napping between museums
1 queen bed
21 – 26 Apr
New place to stay
Apartment in Streeterville
3B Luxury Penthouse w/ Sweeping Views, Pool & Gym
3 beds
21 – 26 Apr
New place to stay
Superhost
Apartment in The Loop
The Playwright's Palace
2 beds
10 – 15 May
New place to stay
Hotel in The Loop
Multipurpose work station and ultra-fast WiFi
1 queen bed
21 – 26 Apr
New place to stay
Guest favourite
Hotel in The Loop
Relaxing Getaway in Chicago w/ View, Pets Welcome!
2 queen beds
12 – 17 May
5.0 out of 5 average rating, 6 reviews
Hotel in The Loop
Explore Chicago! City View, Pet-friendly Property!
1 king bed
21 – 26 Apr
4.45 out of 5 average rating, 11 reviews
Apartment in Magnificent Mile
Standard King Bed Hotel Room at Magnificent Mile
1 king bed
18 – 23 Apr
4.58 out of 5 average rating, 108 reviews
Superhost
Apartment in The Loop
Comfy 2BR-2BTH, Ideally Located!
3 beds
21 – 26 Apr
New place to stay
Apartment in Streeterville
Guest king Room at Aloft Chicago Mag Mile
1 king bed
18 – 23 Apr
New place to stay
Apartment in Streeterville
Guest 2 Queen Room at Aloft Chicago Mag Mile
2 queen beds
18 – 23 Apr
New place to stay
Apartment in Near North Side
The Bulls' Nest: The Chicago Retreat
22 – 27 Apr
New place to stay
Superhost
Apartment in The Loop
Luxury Corner 2 Bedroom in the Loop | Roof Deck
3 beds
30 June – 5 July
4.77 out of 5 average rating, 201 reviews
Superhost
Apartment 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
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
Guest favourite
Apartment in Near North Side
201LOFT | 5 BED, 2.5 BA Downtown Spacious Loft
6 beds
23 – 28 June
4.95 out of 5 average rating, 43 reviews
Guest favourite
Apartment 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
Apartment 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
Guest favourite
Place to stay in River North
Chicago Speakeasy-Style Loft Space (Room 1A)
2 beds
1 – 6 Sept
4.9 out of 5 average rating, 535 reviews
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