Search results; Over 1,000 homes in Chicago

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Guest favorite
Home in Bridgeport
Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
7 guests2 bedrooms3 beds2.5 baths
Aug 22 – 27
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Aug 22 – 27
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R32,134 ZAR for 5 nights

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Shared hotel room in Chicago
Convenient Stay In The Heart of River North
1 single bed
Aug 3 – 8
R3,317 ZAR for 5 nights
4.55 out of 5 average rating, 51 reviews
Guest favorite
Room in Evanston
Stay with JenniferPhotography,
Welcoming Evanston Home
Aug 11 – 16
R9,332 ZAR for 5 nights
4.94 out of 5 average rating, 199 reviews
Place to stay in Chicago
#3/ Cozy Room Close to Blue Line
1 bunk bed
Aug 8 – 13
R3,512 ZAR for 5 nights
New place to stay
Guest favorite
Room in Chicago
Stay with MarcosHosting for 6 years,
Hattie’s House
Aug 11 – 16
R6,989 ZAR for 5 nights
4.93 out of 5 average rating, 167 reviews
Superhost
Room in Chicago
Stay with Mary & Andrew
MasterRoom w/Bath, 2min to Blue LineTrain + Garage
Aug 17 – 22
R10,029 ZAR for 5 nights
4.91 out of 5 average rating, 11 reviews
Top guest favorite
Room in Chicago
Stay with EbonyHosting for 13 years,
Lower Level Oasis - Bed, Bath & Living Rooms
Sep 6 – 11
R7,601 ZAR for 5 nights
5.0 out of 5 average rating, 31 reviews
Superhost
Condo in Chicago
Cabin 304 at 747 Lofts
1 single bed
Aug 4 – 9
R11,659 ZAR for 5 nights
4.84 out of 5 average rating, 97 reviews
Superhost
Room in Chicago
Stay with MaryHosting for 12 years,
Lakefront Room, basement, Safest Neighborhood
Aug 20 – 25
R6,524 ZAR for 5 nights
4.81 out of 5 average rating, 78 reviews
Guest favorite
Room in Chicago
Stay with ZhengI am a realtor,
Chicago Chinatown Center A
Aug 3 – 8
R8,488 ZAR for 5 nights
5.0 out of 5 average rating, 6 reviews
Guest favorite
Room in Chicago
Stay with DeniseHosting for 5 years,
BOHEMIAN LODGE #1 (clean & affordable travel)
Aug 10 – 15
R7,432 ZAR for 5 nights
4.87 out of 5 average rating, 197 reviews
Guest favorite
Room in Chicago
Stay with AtakanCloudreach,
Private Room & Shared Bathroom | Workstation
Aug 11 – 16
R7,149 ZAR for 5 nights
4.93 out of 5 average rating, 15 reviews
Room in Chicago
Stay with GenovaLmt, cmldt, hvac,
Explore More in Room 4
Aug 11 – 18
R5,224 ZAR for 7 nights
4.86 out of 5 average rating, 43 reviews
Room in Chicago
Stay with GenovaLmt, cmldt, hvac,
Spoon Cacoon- Room 1
Oct 3 – 9
R3,805 ZAR for 6 nights
4.67 out of 5 average rating, 95 reviews
Superhost
Room in Chicago
Stay with RyanComputer science,
"Wine" Room - 1 block from train, Victorian Charm
Sep 21 – 26
R5,186 ZAR for 5 nights
4.76 out of 5 average rating, 524 reviews
Room in Chicago
Stay with RoseannaInvestor,
Beautiful Private Room 5 min to the City
Aug 17 – 22
R8,593 ZAR for 5 nights
4.79 out of 5 average rating, 80 reviews
Guest favorite
Room in Melrose Park
Stay with ToniSales,
4 miles to Airport, King bed, 45 in TV
Sep 2 – 7
R6,862 ZAR for 5 nights
4.98 out of 5 average rating, 86 reviews
Room in Chicago
Stay with Nala And OwenHosting for 7 years,
Fashionable Room w/ full bathroom - FREE PARKING!
Aug 12 – 17
R8,826 ZAR for 5 nights
4.77 out of 5 average rating, 254 reviews
Guest favorite
Apartment in Berwyn
Private apartment with retro vibe
2 beds
Aug 10 – 15
R10,240 ZAR for 5 nights
4.92 out of 5 average rating, 398 reviews