South Side
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Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
Fully refundable
The price is CA $216 per night from Sep 22 to Sep 23
CA $216
CA $254 total
Sep 22 - Sep 23
includes taxes & fees
Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the overall value in our reviews. ...
7/10 Good! (1,002 reviews)
"Good"
Reviewed on Sep 12, 2026
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
The price is CA $211 per night from Sep 27 to Sep 28
CA $211
CA $261 total
Sep 27 - Sep 28
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
Jaslin Hotel
261 West Cermak Rd Chicago IL
The price is CA $223 per night from Sep 23 to Sep 24
CA $223
CA $265 total
Sep 23 - Sep 24
includes taxes & fees
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,359 reviews)
"Love the place, the employees, the restaurants, and the parking!"
Reviewed on Sep 12, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Bright Vintage U of C Center Condo with WiFi, AC in enjoyable Chicago
Chicago IL
Stay at this condo in Chicago. Enjoy free WiFi, laundry facilities, and balconies. Popular attractions Soldier Field and Griffin Museum of Science and Industry ...
8/10 Very good! (5 reviews)
"The queen beds were comfortable and the parking was easy. It was nice that there were so many bathrooms, so no one ever had to wait. There was no bedding for the futons/couch, we found a thin blanket to use as a sheet and we happened to bring a blanket with us, so we made do. In the common areas ..."
Reviewed on Aug 10, 2026
Townhome 3 bedroom 2 bath with Parking - near McCormick Place , Chinatown Sox
Chicago IL
Stay at this vacation home in Chicago. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Soldier Field and Grant Park are located ...
10/10 Exceptional! (6 reviews)
"There was no issues during our stay and the rules are very reasonable. One thing to note is the location of the home which steps away from Chinatown, and a couple of minutes away from downtown. The home is very secure and spacious. The bathrooms, kitchen, and bedrooms were very clean. There was hot ..."
Reviewed on Aug 21, 2026
Bronzeville Manor walking distance to hospitals
Chicago IL
Stay at this condo in Chicago. Enjoy free WiFi. Popular attractions Soldier Field and Grant Park are located nearby.
9.6/10 Exceptional! (26 reviews)
"It was a lovely place to stay for my first time using VRBO. Will definitely stay here again next time I'm in Chicago."
Reviewed on Aug 9, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular South Side attractions
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $56
per adult
94% of travellers recommend
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