Search results; Over 1,000 homes in Chicago

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Guest favorite
Townhouse in West Town
Chicago West Town Row House
8 guests3 bedrooms4 beds1.5 baths
Aug 17 – 22
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Aug 17 – 22
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R35,805 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
Hotel in Chicago
Playful spirit and sustainable practices
1 queen bed
Aug 10 – 15
R12,844 ZAR for 5 nights
4.56 out of 5 average rating, 538 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
Guest favorite
Room in Chicago
Stay with MiguelProperty managment,
B: Spacious bedroom with private workspace.
Sep 2 – 7
R4,975 ZAR for 5 nights
4.85 out of 5 average rating, 39 reviews
Guest favorite
Room in Chicago
Stay with ZhengI am a realtor,
Chicago Chinatown Center A
Aug 3 – 8
R8,313 ZAR for 5 nights
5.0 out of 5 average rating, 6 reviews
Guest favorite
Room in Oak Park
Stay with RicardoRetired,
lovely suite
Sep 24 – 29
R6,655 ZAR for 5 nights
4.9 out of 5 average rating, 125 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
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 ErikHosting for 11 years,
The Red Room
Sep 7 – 12
R4,394 ZAR for 5 nights
4.85 out of 5 average rating, 396 reviews
Top guest favorite
Guesthouse in Chicago
Cozy Coach House
1 queen bed
Aug 3 – 8
R9,950 ZAR for 5 nights
4.95 out of 5 average rating, 435 reviews
Superhost
Home in Berwyn
Chicago Buddha's Abode
2 queen beds
Aug 12 – 17
R15,141 ZAR for 5 nights
New place to stay
Hotel in Chicago
Standard King Bed Hotel Room at Magnificent Mile
1 king bed
Aug 10 – 15
R14,354 ZAR for 5 nights
4.62 out of 5 average rating, 204 reviews
Guest favorite
Room in Evanston
Stay with JenniferPhotography,
Welcoming Evanston Home
Aug 22 – 27
R9,046 ZAR for 5 nights
4.94 out of 5 average rating, 201 reviews
Superhost
Room in Franklin Park
Stay with SandyReal estate,
Victorian Gorgeous room
Aug 5 – 10
R9,498 ZAR for 5 nights
4.81 out of 5 average rating, 257 reviews
Superhost
Apartment in Chicago
Cool spot in cool neighborhood
1 double bed
Aug 20 – 25
R6,461 ZAR for 5 nights
4.73 out of 5 average rating, 11 reviews
Guest favorite
Room in Chicago
Stay with GenovaLmt, cmldt, hvac,
Sweet Pea - Blue Key - Place 3
Aug 24 – 29
R4,179 ZAR for 5 nights
5.0 out of 5 average rating, 14 reviews
Guest suite in Chicago
Modern Basement Retreat
1 double bed
Oct 27 – Nov 1
R7,538 ZAR for 5 nights
New place to stay