Search results; Over 1,000 homes in Chicago

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Guest favorite
Apartment in Lake View
An elegant Chicago Northside Getaway
6 guests3 bedrooms3 beds1 bath
Aug 23 – 28
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Aug 23 – 28
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R22,980 ZAR for 5 nights

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Hotel in Chicago
Classic luxury on iconic Michigan Ave
1 king bed
Aug 10 – 15
R12,182 ZAR for 5 nights
4.58 out of 5 average rating, 1050 reviews
Shared hotel room in Chicago
Convenient Stay In The Heart of River North
1 single bed
Aug 10 – 15
R2,330 ZAR for 5 nights
4.53 out of 5 average rating, 57 reviews
Room in Chicago
Stay with Nelson
K7. Next to Downtown
Aug 3 – 8
R2,994 ZAR for 5 nights
4.41 out of 5 average rating, 41 reviews
Guest favorite
Room in Des Plaines
Stay with ValentinBuilder,
R3 Comfy private room overlooking the forestland.
Aug 17 – 22
R8,227 ZAR for 5 nights
4.88 out of 5 average rating, 388 reviews
Hotel in Chicago
Playful spirit and sustainable practices
1 queen bed
Aug 7 – 12
R16,079 ZAR for 5 nights
4.56 out of 5 average rating, 538 reviews
Room in Chicago
Stay with SergioHosting for 7 years,
J2.Next to Downtown!By bus to go straight Downtown
Aug 4 – 9
R3,016 ZAR for 5 nights
4.2 out of 5 average rating, 286 reviews
Apartment in Berwyn
Cozy and fun all together!
1 queen bed
Aug 19 – 24
R8,906 ZAR for 5 nights
New place to stay
Apartment in Chicago
Stunning condo in central location
1 bed
Aug 17 – 22
R11,910 ZAR for 5 nights
New place to stay
Superhost
Place to stay in Chicago
Cozy, Quiet, Private bathroom in private room
1 bed
Sep 2 – 7
R4,760 ZAR for 5 nights
4.78 out of 5 average rating, 188 reviews
Room in Chicago
Stay with SergioHosting for 7 years,
J55. Next to downtown Chicago
Aug 3 – 8
R2,994 ZAR for 5 nights
4.32 out of 5 average rating, 92 reviews
Superhost
Hotel in Chicago
A polished, modern affair on iconic Michigan Ave.
1 double bed
Aug 3 – 8
R17,607 ZAR for 5 nights
4.77 out of 5 average rating, 298 reviews
Hotel in Chicago
1927 gem, once home of Capone Speakeasy
2 double beds
Aug 4 – 9
R17,139 ZAR for 5 nights
4.63 out of 5 average rating, 332 reviews
Guest favorite
Room in Chicago
Stay with MiguelProperty managment,
B: Spacious bedroom with private workspace.
Sep 2 – 7
R4,954 ZAR for 5 nights
4.85 out of 5 average rating, 39 reviews
Room in Chicago
Stay with Jose
R5 Close to Downtown Small Room
Aug 4 – 9
R3,080 ZAR for 5 nights
4.73 out of 5 average rating, 33 reviews
Guest favorite
Room in Chicago
Stay with ZhengI am a realtor,
Chicago Chinatown Center A
Aug 3 – 8
R8,378 ZAR for 5 nights
5.0 out of 5 average rating, 6 reviews
Superhost
Room in Franklin Park
Stay with SandyReal estate,
Victorian Gorgeous room
Aug 5 – 10
R9,326 ZAR for 5 nights
4.81 out of 5 average rating, 257 reviews
Room in Chicago
Stay with Aaron EmisaelHosting for 8 years,
P997. Next to Downtown
Aug 5 – 10
R4,071 ZAR for 5 nights
4.86 out of 5 average rating, 14 reviews
Top guest favorite
Apartment in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
2 beds
Nov 9 – 14
R14,538 ZAR for 5 nights
5.0 out of 5 average rating, 40 reviews