Search results; 392 places

Top guest favorite
Apartment in Near West Side
KING bed FREE P-Spot EV EZZY Accessible NO stairs
4 beds
Jul 13 – 18
R23,724 ZAR for 5 nights, originally R35,826 ZAR
4.99 out of 5 average rating, 141 reviews
Guest favorite
Apartment in Near West Side
Free Parking| King Bed |Private Balcony |Sleeps 8
4 beds
Jul 10 – 15
R25,604 ZAR for 5 nights, originally R50,908 ZAR
4.98 out of 5 average rating, 120 reviews
Top guest favorite
Apartment in Magnificent Mile
Elegant Suite in Gold Coast
Free cancellation
Sep 27 – Oct 2
R31,723 ZAR for 5 nights
4.98 out of 5 average rating, 163 reviews
Top guest favorite
Apartment in Near North Side
Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D
2 queen beds
Sep 28 – Oct 3
R19,181 ZAR for 5 nights
4.97 out of 5 average rating, 246 reviews
Guest favorite
Apartment in Streeterville
Guild #2 | Gold Coast Mag Mile Best Location
4 beds
Aug 4 – 9
R40,860 ZAR for 5 nights, originally R45,759 ZAR
4.85 out of 5 average rating, 179 reviews
Apartment in The Loop
Cozy 1BR in South Loop | Convenience in the City
Free cancellation
Nov 2 – 7
R13,042 ZAR for 5 nights, originally R14,333 ZAR
4.69 out of 5 average rating, 134 reviews
Superhost
Apartment in Gold Coast
Gold Coast Getaway
Free cancellation
Aug 19 – 24
R26,676 ZAR for 5 nights, originally R30,033 ZAR
4.78 out of 5 average rating, 37 reviews
Superhost
Place to stay in Chicago
McCormick221, Chinatown, SOX, GrantPark
1 double bed
Aug 4 – 9
R10,522 ZAR for 5 nights
4.88 out of 5 average rating, 146 reviews
Guest favorite
Apartment in Bridgeport
Blue Brick Apartment in Bridgeport - Park for Free
Free cancellation
Aug 4 – 9
R20,790 ZAR for 5 nights
4.94 out of 5 average rating, 149 reviews
Superhost
Room in Woodlawn
Stay with ClaraHealthcare it,
Condo Living! 5 mins from UChicago/Obama Center
Jul 10 – 15
R9,041 ZAR for 5 nights
5.0 out of 5 average rating, 4 reviews
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Top guest favorite
Home in Gold Coast
Gold Coast Home|Rooftop |PoolTable |Parking |Views
6 beds
Aug 9 – 14
R100,986 ZAR for 5 nights, originally R125,922 ZAR
5.0 out of 5 average rating, 33 reviews
Top guest favorite
Apartment in Magnificent Mile
Pristine Gold Coast 3BD|2BA | Free Parking| Beach.
Free cancellation
Aug 18 – 23
R71,558 ZAR for 5 nights
5.0 out of 5 average rating, 10 reviews
Guest favorite
Apartment in Old Town
Old Town Tranquility (+parking)
2 beds
Aug 9 – 14
R27,417 ZAR for 5 nights
4.98 out of 5 average rating, 50 reviews
Guest favorite
Apartment in East Rogers Park
1 bedroom apt near Michigan Lake
Jul 10 – 15
R14,695 ZAR for 5 nights, originally R17,971 ZAR
4.91 out of 5 average rating, 68 reviews
Apartment in Near North Side
Stunning Gold Coast Studio
Free cancellation
Oct 26 – 31
R16,408 ZAR for 5 nights
4.91 out of 5 average rating, 11 reviews
Guest favorite
Apartment in Near West Side
Downtown 10 min FREE indoor Park sleeps 12-2 Baths
5 beds
Jul 10 – 15
R27,394 ZAR for 5 nights, originally R57,515 ZAR
4.98 out of 5 average rating, 46 reviews
Guest favorite
Apartment in Magnificent Mile
Luxury 3BR Duplex in Prime Location
4 beds
Jul 19 – 24
R88,970 ZAR for 5 nights
5.0 out of 5 average rating, 68 reviews
Guest favorite
Home in Near North Side
Private Downtown Retreat with Rooftop Oasis
Free cancellation
Sep 12 – 17
R87,860 ZAR for 5 nights, originally R102,465 ZAR
4.98 out of 5 average rating, 61 reviews