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Search results; Over 1,000 places

Hotel in River North
Playful spirit and sustainable practices
1 queen bed
Apr. 1 – 6
4.42 out of 5 average rating, 108 reviews
Superhost
Apartment in Near West Side
Stylish CityView Condo W/Pool
1 queen bed
Apr. 14 – 19
5.0 out of 5 average rating, 4 reviews
Hotel in Magnificent Mile
Classic luxury on iconic Michigan Ave
1 king bed
Apr. 1 – 6
5.0 out of 5 average rating, 3 reviews
Apartment in Near North Side
Kasa | Enjoy City Views on Your Balcony | Chicago
1 queen bed
Apr. 1 – 6
4.84 out of 5 average rating, 384 reviews
Hotel room in Near North Side
Hotel Perks - Private Bedroom | Private Bathroom
1 queen bed
Apr. 1 – 6
4.48 out of 5 average rating, 3600 reviews
Apartment in Streeterville
Guest 2 Queen Room at Aloft Chicago Mag Mile
2 queen beds
Apr. 1 – 6
New place to stay
Apartment in Streeterville
Guest king Room at Aloft Chicago Mag Mile
1 king bed
Apr. 1 – 6
New place to stay
Boutique hotel in Magnificent Mile
Allerton King with City View
1 king bed
Apr. 7 – 12
4.69 out of 5 average rating, 36 reviews
Boutique hotel in Gold Coast
Luxury Stay - Claridge House, Queen Room
1 queen bed
Apr. 7 – 12
4.41 out of 5 average rating, 652 reviews
Hotel in The Loop
A polished, modern affair on iconic Michigan Ave.
1 double bed
Apr. 1 – 6
4.81 out of 5 average rating, 36 reviews
Hotel in River North
Godfrey Hotel Lifestyle Rooftop 4.5*-King Deluxe
1 king bed
Apr. 1 – 6
4.54 out of 5 average rating, 1174 reviews
Superhost
Room in River North
Stay with MichaelStay-at-home mom,
Artist Loft. Middle Room
Jun. 4 – 9
4.8 out of 5 average rating, 5 reviews
Guest favourite
Apartment in Near North Side
*Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D
2 queen beds
Apr. 7 – 12
4.99 out of 5 average rating, 98 reviews
Apartment in Chicago
The Metropolitan Retreat (2BD/2BA)
3 beds
Apr. 6 – 11
4.85 out of 5 average rating, 20 reviews
Guest favourite
Apartment in The Loop
Loop Loft-Subway & Art Institute
1 queen bed
Apr. 6 – 11
4.92 out of 5 average rating, 13 reviews
Guest favourite
Apartment in Chicago
Stunning Panoramic Chicago Views & Free Parking
2 beds
Apr. 15 – 20
4.86 out of 5 average rating, 150 reviews
Guest favourite
Apartment in The Loop
Bright 2BR-2BA steps from The Bean & Michigan Ave
2 beds
Apr. 20 – 25
4.9 out of 5 average rating, 100 reviews
Guest favourite
Apartment in Magnificent Mile
Urban Oasis in Vibrant Gold Coast
1 bed
Jul. 6 – 11
4.95 out of 5 average rating, 22 reviews