Search results; 282 places

Guest favorite
Hotel in Chicago
Light-flooded rooms and city views
10 min drive
Jun 18 – 23
R34,066 ZAR for 5 nights
for 5 nights
4.92 out of 5 average rating, 79 reviews
Hotel in Chicago
modern design with VU Skyward rooftop bar
20 min drive
Jun 13 – 18
R18,151 ZAR for 5 nights
for 5 nights
4.65 out of 5 average rating, 37 reviews
Home in Chicago
LUXURY - Movie Theater + Spa House
20 min drive
Oct 1 – 6
R15,527 ZAR for 5 nights
for 5 nights
New place to stay
Guest favorite
Hotel in Rosemont
Relaxing Standard Room l Free Airport Shuttle
50 min drive
Jun 13 – 18
R18,498 ZAR for 5 nights
for 5 nights
4.93 out of 5 average rating, 268 reviews
Superhost
Hotel in Itasca
Guest room with 2 Double Beds + PET Friendly
60 min drive
Jun 29 – Jul 4
R9,686 ZAR for 5 nights
for 5 nights
4.86 out of 5 average rating, 170 reviews
Superhost
Apartment in Chicago
Design + Views in Fulton Market | The Frame
10 min drive
Jul 13 – 18
R68,996 ZAR for 5 nights
for 5 nights
4.94 out of 5 average rating, 31 reviews
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More stays available for your dates

Hotel in Chicago
Spot-on location near Mag Mile shops
20 min drive
Jun 22 – 27
R16,806 ZAR for 5 nights
for 5 nights
4.75 out of 5 average rating, 4 reviews
Superhost
Apartment in Chicago
Most Stylish Apartments You’ll Ever Stay In|TheNeo
10 min drive
Jun 13 – 18
R44,130 ZAR for 5 nights, originally R68,354 ZAR
for 5 nights
4.83 out of 5 average rating, 12 reviews
Superhost
Apartment in Chicago
The South Loop Suite
20 min drive
Jun 23 – 28
R33,420 ZAR for 5 nights, originally R38,130 ZAR
for 5 nights
5.0 out of 5 average rating, 4 reviews
Superhost
Hotel in Itasca
King Bed at Chicago Northwest + PET Friendly
60 min drive
Jun 15 – 20
R12,992 ZAR for 5 nights
for 5 nights
4.8 out of 5 average rating, 362 reviews
Guest favorite
Apartment in Chicago
Lincoln Park Haven: Balcony, Walk to Whole Foods
20 min drive
Jun 29 – Jul 4
R37,112 ZAR for 5 nights
for 5 nights
4.92 out of 5 average rating, 37 reviews
Guesthouse in Chicago
Andersonville Luxury Pool Escape
30 min drive
Jun 29 – Jul 4
R40,137 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 3 reviews
Superhost
Apartment in Chicago
Luxe Suite + Spa House! Key West Vibes 4-Seasons
20 min drive
Aug 17 – 22
R17,421 ZAR for 5 nights, originally R18,901 ZAR
for 5 nights
4.88 out of 5 average rating, 103 reviews
Top guest favorite
Apartment in Chicago
Fun & cozy getaway w/POOL/game room/FREE parking
20 min drive
Aug 17 – 22
R20,660 ZAR for 5 nights, originally R22,517 ZAR
for 5 nights
4.97 out of 5 average rating, 110 reviews
Guest favorite
Apartment in Chicago
Luxe Ranch & Spa, Euro Opulence, a 4-Season Oasis
20 min drive
Sep 28 – Oct 3
R22,123 ZAR for 5 nights, originally R23,895 ZAR
for 5 nights
4.98 out of 5 average rating, 103 reviews
Guest favorite
Apartment in Chicago
50th Floor Mag Mile VIEWS, Balcony, Pool, Gym
20 min drive
Jun 14 – 19
R25,076 ZAR for 5 nights
for 5 nights
4.87 out of 5 average rating, 47 reviews
Superhost
Apartment in Chicago
Sentral Premium 2BR Apt South Loop Chicago
20 min drive
Jun 29 – Jul 4
R35,059 ZAR for 5 nights, originally R39,791 ZAR
for 5 nights
4.67 out of 5 average rating, 311 reviews
Hotel in Oakbrook Terrace
Your Oak Brook Escape| Free Parking & Pet-friendly
50 min drive
Jun 13 – 18
R10,148 ZAR for 5 nights
for 5 nights
4.38 out of 5 average rating, 61 reviews