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Search results; Over 1,000 places

Boutique hotel in Magnificent Mile
Allerton King with City View
Professional Host
7–12 Apr
4.69 out of 5 average rating, 36 reviews
Flat in The Loop
Millennium Park Paradise (2BD/2BA)
Individual Host
24–29 Apr
4.67 out of 5 average rating, 73 reviews
Hotel in Magnificent Mile
Classic luxury on iconic Michigan Ave
1 king bed
1–6 Apr
5.0 out of 5 average rating, 3 reviews
Superhost
Flat in The Loop
Luxury Corner 2 Bedroom in the Loop | Roof Deck
Professional Host
20–25 Apr
4.76 out of 5 average rating, 199 reviews
Guest favourite
Place to stay in River North
Chicago Speakeasy-Style Loft Space (Room 1A)
Professional Host
1–6 Sept
4.9 out of 5 average rating, 532 reviews
Guest favourite
Place to stay in River North
Chicago Speakeasy-Style Loft Space (Room 2A)
Professional Host
21–26 Apr
4.86 out of 5 average rating, 328 reviews
Flat in Near North Side
The Bulls' Nest: The Chicago Retreat
1–6 Apr
New place to stay
Superhost
Flat in The Loop
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Professional Host
1–6 Apr
4.78 out of 5 average rating, 153 reviews
Guest favourite
Flat in Streeterville
Lake, City, & River View Condo
Professional Host
6–11 Apr
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Magnificent Mile
Urban Chic Apartment by the Magnificent Mile
Individual Host
24–29 Sept
4.94 out of 5 average rating, 212 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, 80 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, 41 reviews
Superhost
Flat in The Loop
Cozy 2BR-2BA steps from 'The Bean' & Michigan Ave
Individual Host
20–25 Apr
4.92 out of 5 average rating, 130 reviews
Superhost
Flat in The Loop
STUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
Individual Host
6–11 Apr
5.0 out of 5 average rating, 6 reviews
Luxe
Flat in The Loop
Cloud9|XL Penthouse near the Bean| The Stella
Professional Host
1–6 Apr
Guest favourite
Flat in Near North Side
55/56 Floor VIEW, Pool, Fireplace, Fitness Center.
4 beds
1–6 Apr
5.0 out of 5 average rating, 23 reviews
Guest favourite
Flat in Near North Side
50th Floor Mag Mile Studio
1 bed
21–26 Apr
4.93 out of 5 average rating, 56 reviews
Flat in Near North Side
Downtown Riverwalk Music Inspired Loft
3 beds
1–6 Apr
4.76 out of 5 average rating, 41 reviews