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Search results; Over 1,000 places

Boutique hotel in Gold Coast
Luxury Stay - Claridge House, Queen Room
1 queen bed
Apr 28 – May 3
4.43 out of 5 average rating, 686 reviews
Shared hotel room in Near North Side
Traveler's Dream - 1 bed in a shared bedroom
1 bunk bed
Apr 18 – 23
4.52 out of 5 average rating, 1679 reviews
Hotel room in Near North Side
Hotel Perks - Private Bedroom | Private Bathroom
1 queen bed
Apr 18 – 23
4.48 out of 5 average rating, 3618 reviews
Apartment in Magnificent Mile
Standard King Bed Hotel Room at Magnificent Mile
1 king bed
Apr 20 – 25
4.58 out of 5 average rating, 108 reviews
Hotel in River North
Godfrey Hotel Lifestyle Rooftop 4.5*-King Deluxe
1 king bed
Apr 18 – 23
4.54 out of 5 average rating, 1214 reviews
Apartment in Magnificent Mile
Standard Double Hotel Room at Magnificent Mile
2 double beds
Apr 20 – 25
4.75 out of 5 average rating, 155 reviews
Boutique hotel in River North
Sonder at Found Chicago | Queen Room
1 queen bed
Apr 18 – 23
4.32 out of 5 average rating, 87 reviews
Guest favorite
Apartment in The Loop
Bright 2BR-2BA steps from The Bean & Michigan Ave
2 beds
Apr 20 – 25
4.91 out of 5 average rating, 106 reviews
Apartment in Streeterville
Guest king Room at Aloft Chicago Mag Mile
1 king bed
Apr 18 – 23
New place to stay
Apartment in The Loop
Sonder The Plymouth | Superior 3BR Apt
3 double beds
Apr 21 – 26
4.58 out of 5 average rating, 385 reviews
Apartment in Near North Side
Kasa | Enjoy City Views on Your Balcony | Chicago
1 queen bed
Apr 21 – 26
4.84 out of 5 average rating, 415 reviews
Apartment in The Loop
Sentral Premium 2BR Apt South Loop Chicago
2 queen beds
Apr 21 – 26
4.62 out of 5 average rating, 234 reviews
Superhost
Apartment in Chicago
McCormick 2B/2Ba for up to 6 guests w Opt Parking
3 beds
Apr 21 – 26
New place to stay
Superhost
Apartment in The Loop
Comfy 2BR-2BTH, Ideally Located!
3 beds
Apr 21 – 26
New place to stay
Apartment in Streeterville
Guest 2 Queen Room at Aloft Chicago Mag Mile
2 queen beds
Apr 18 – 23
New place to stay
Guest favorite
Apartment in Magnificent Mile
Elegant Suite in Gold Coast
1 king bed
Jul 24 – 29
4.98 out of 5 average rating, 83 reviews
Guest favorite
Condo in West Loop
Updated Designer Duplex In Fulton Market W/parking
5 beds
May 26 – 31
4.95 out of 5 average rating, 175 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