Search results; 268 places

Hotel in Streeterville
Easy walk to the lakefront & Navy Pier
10 min drive
Jun 15 – 20
R21,404 ZAR for 5 nights
for 5 nights
4.8 out of 5 average rating, 5 reviews
Hotel in South Loop
modern design with VU Skyward rooftop bar
20 min drive
Jun 15 – 20
R18,814 ZAR for 5 nights
for 5 nights
4.65 out of 5 average rating, 37 reviews
Guest favorite
Hotel in West Loop
Light-flooded rooms and city views
20 min drive
Jun 28 – Jul 3
R23,079 ZAR for 5 nights
for 5 nights
4.92 out of 5 average rating, 79 reviews
Guest favorite
Apartment in River North
50th Floor Mag Mile Studio
10 min drive
Jun 25 – 30
R26,096 ZAR for 5 nights, originally R31,284 ZAR
for 5 nights
4.9 out of 5 average rating, 99 reviews
Guest favorite
Apartment in Chicago Loop
Panoramic 2BR Penthouse in the Sky | Roof Deck
20 min drive
Jul 26 – 31
R52,851 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 11 reviews
Superhost
Apartment in Chicago Loop
The Professional's Playground
20 min drive
Jun 22 – 27
R16,757 ZAR for 5 nights
for 5 nights
4.71 out of 5 average rating, 63 reviews
Guest favorite
Apartment in Chicago Loop
The Parkside Pavilion
20 min drive
Aug 16 – 21
R26,585 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 14 reviews
Guest favorite
Apartment in River North
50th Floor Mag Mile VIEWS, Balcony, Pool, Gym
10 min drive
Jun 23 – 28
R26,819 ZAR for 5 nights, originally R30,977 ZAR
for 5 nights
4.87 out of 5 average rating, 47 reviews
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More stays available for your dates

Superhost
Apartment in South Loop
The South Loop Suite
20 min drive
Jun 23 – 28
R33,018 ZAR for 5 nights, originally R38,270 ZAR
for 5 nights
5.0 out of 5 average rating, 4 reviews
Superhost
Apartment in South Loop
South Loop | Rooftop With In & Out Parking | 2
20 min drive
Jun 22 – 27
R28,169 ZAR for 5 nights, originally R38,127 ZAR
for 5 nights
4.55 out of 5 average rating, 11 reviews
Hotel room in River North
Haven of Serenity! Pets Allowed, Onsite Pool
10 min drive
Jun 16 – 21
R27,135 ZAR for 5 nights
for 5 nights
4.53 out of 5 average rating, 80 reviews
Superhost
Apartment in South Loop
Sentral Premium 2BR Apt South Loop Chicago
20 min drive
Jun 16 – 21
R44,516 ZAR for 5 nights, originally R50,524 ZAR
for 5 nights
4.67 out of 5 average rating, 311 reviews
Superhost
Apartment in River North
52nd Floor MagMile Penthouse VIEWS Fireplace Pool
10 min drive
Jun 26 – Jul 1
R35,894 ZAR for 5 nights, originally R45,492 ZAR
for 5 nights
4.9 out of 5 average rating, 52 reviews
Guest favorite
Apartment in Near North Side
Exclusive Gold Coast 2BR: Balcony, Walkable
20 min drive
Aug 21 – 26
R57,218 ZAR for 5 nights
for 5 nights
4.89 out of 5 average rating, 81 reviews
Superhost
Apartment in South Loop
The Professional's Playground (2BD / 2BA)
20 min drive
Jul 13 – 18
R32,870 ZAR for 5 nights
for 5 nights
4.92 out of 5 average rating, 84 reviews
Superhost
Apartment in South Loop
14th Floor 3Bd 3Bth Unit w/ Gym, Pool, &Amenities
20 min drive
Jul 14 – 19
R59,817 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 3 reviews
Hotel in River North
Cozy lobby fireplace & onsite brasserie
10 min drive
Jun 15 – 20
R20,680 ZAR for 5 nights
for 5 nights
New place to stay
Guest favorite
Apartment in Magnificent Mile
Luxury Designer Penthouse NW | Pool | Gold Coast
20 min drive
Jul 24 – 29
R103,104 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 8 reviews