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Search results; Over 1,000 places

Guest favorite
Apartment in Uptown
Cozy loft in Chicago's Uptown
2 min walk
Oct 7 – 12
4.96 out of 5 average rating, 264 reviews
Superhost
Apartment in Edgewater
Lovely Uptown Haven
11 min walk
Apr 28 – May 3
New place to stay
Guest favorite
Room in Uptown
Spacious Bedroom in Modern Condo w/private bath
4 min walk
May 19 – 24
4.99 out of 5 average rating, 109 reviews
Apartment in Uptown
Vibrant studio at Uptown by Red Line (02)
5 min walk
Apr 22 – 27
4.78 out of 5 average rating, 130 reviews
Superhost
Apartment in Uptown
Modern Uptown Apartment - Clean & Close to Train!
4 min walk
May 6 – 11
4.86 out of 5 average rating, 110 reviews
Superhost
Apartment in Uptown
Dapper Uptown Studio near the Lake
4 min walk
Apr 24 – 29
4.8 out of 5 average rating, 99 reviews
Superhost
Apartment in Andersonville
Lovely Andersonville Apt with Ideal Location
11 min walk
Jul 7 – 12
4.82 out of 5 average rating, 434 reviews
Guest favorite
Condo in Uptown
Near Lake Michigan & Wrigley Field
3 min walk
Apr 26 – May 1
4.98 out of 5 average rating, 199 reviews
Guest favorite
Room in Uptown
Cozy private room near lake and transport.
11 min walk
Jul 7 – 12
4.99 out of 5 average rating, 84 reviews
Guest favorite
Guesthouse in Andersonville
Private, Charming, Coach House Loft in Andersonville
13 min walk
Apr 28 – May 3
4.91 out of 5 average rating, 340 reviews
Guest favorite
Apartment in Uptown
Huge Apt in Uptown/Andersonville
12 min walk
Apr 25 – 30
4.95 out of 5 average rating, 197 reviews
Guest favorite
Apartment in Andersonville
Sunny, Cozy, Colorful Andersonville
8 min drive
May 12 – 17
4.96 out of 5 average rating, 252 reviews
Guest favorite
Apartment in Uptown
❤️ New and Clean! Big Apartment with Parking
4 min walk
Jun 16 – 21
4.97 out of 5 average rating, 143 reviews
Guest favorite
Room in Uptown
UPTOWN ROW HOUSE-SPACIOUS PRIVATE SHARED ROOM(S)
4 min walk
Apr 20 – 25
4.96 out of 5 average rating, 138 reviews
Guest favorite
Condo in Uptown
Stunning, Spacious, & Sun-Soaked 1br Uptown Condo
10 min walk
Apr 27 – May 2
4.92 out of 5 average rating, 110 reviews
Guest favorite
Apartment in Uptown
Whole Flat in Private Club. Walk to L, Dining & Shows
1 min walk
Jun 1 – 6
4.89 out of 5 average rating, 462 reviews
Guest favorite
Condo in Andersonville
Warm & Comforting 4br/2ba In Andersonville
8 min drive
Apr 28 – May 3
4.91 out of 5 average rating, 144 reviews
Guest favorite
Apartment in Uptown
❤️ Lowest Rates! Spacious Duplex with Parking!
4 min walk
Jun 13 – 18
4.92 out of 5 average rating, 132 reviews