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Search results; Over 1,000 places

Hotel in River North
Playful spirit and sustainable practices
9 min drive
Apr 1 – 6
4.42 out of 5 average rating, 108 reviews
Superhost
Apartment in The Loop
Cloud9|Pool&BBQ|Millen Park|Movie Theater|The Ford
2 min walk
Apr 14 – 19
4.94 out of 5 average rating, 34 reviews
Guest favorite
Apartment in The Loop
Loop Loft-Subway & Art Institute
9 min walk
Apr 6 – 11
4.92 out of 5 average rating, 13 reviews
Hotel in Magnificent Mile
Classic luxury on iconic Michigan Ave
13 min drive
Apr 1 – 6
5.0 out of 5 average rating, 3 reviews
Guest favorite
Boutique hotel in The Loop
King Room in Theatre District
6 min walk
Apr 14 – 19
4.87 out of 5 average rating, 15 reviews
Apartment in Streeterville
Guest king Room at Aloft Chicago Mag Mile
11 min drive
Apr 1 – 6
New place to stay
Hotel in The Loop
A polished, modern affair on iconic Michigan Ave.
9 min drive
Apr 1 – 6
4.81 out of 5 average rating, 36 reviews
Apartment in The Loop
Sonder Jewelers Row | One-Bedroom Apartment
6 min walk
Apr 1 – 6
4.6 out of 5 average rating, 271 reviews
Apartment in The Loop
The Professional's Playground
6 min walk
May 11 – 16
4.8 out of 5 average rating, 20 reviews
Guest favorite
Hotel in The Loop
2 Queen Bedroom in Downton
6 min walk
Apr 21 – 26
4.86 out of 5 average rating, 93 reviews
Superhost
Room in River North
Artist Loft. Middle Room
12 min walk
Jun 4 – 9
4.8 out of 5 average rating, 5 reviews
Superhost
Apartment in The Loop
Cozy 2BR-2BA steps from 'The Bean' & Michigan Ave
7 min walk
Apr 20 – 25
4.92 out of 5 average rating, 129 reviews
Guest favorite
Apartment in The Loop
Homey 2BR-2BA steps from The Bean & Michigan Ave
7 min walk
Apr 28 – May 3
4.95 out of 5 average rating, 137 reviews
Superhost
Apartment in The Loop
Cloud9 | Up to 15 ppl Millenium Park | The Jordan
2 min walk
Apr 22 – 27
5.0 out of 5 average rating, 3 reviews
Luxe
Apartment in The Loop
Cloud9|XL Penthouse near the Bean| The Stella
9 min walk
Apr 1 – 6
Boutique hotel in Magnificent Mile
Allerton King with City View
10 min drive
Apr 7 – 12
4.69 out of 5 average rating, 36 reviews
Superhost
Apartment in The Loop
Luxury Corner 2 Bedroom in the Loop | Roof Deck
11 min walk
Apr 20 – 25
4.76 out of 5 average rating, 199 reviews
Apartment in The Loop
Spacious & Stylish 2BR-2BA Apt Steps from The Bean
7 min walk
Apr 21 – 26
4.78 out of 5 average rating, 132 reviews