South Side Cheap Vacations

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Flight and Cheap hotel deals in South Side

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

Near South Side
CA $1,900
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (1,276 reviews)
Great staff

Reviewed on Aug 29, 2026

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3 Night Cheap holidays in South Side

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

Near South Side
CA $1,900
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (1,276 reviews)
Great staff

Reviewed on Aug 29, 2026

Don't see what you're looking for?
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4 Night Cheap holidays in South Side

Price found within the past 48 hours. Click for updated prices.
Chinatown Hotel Chicago

Chinatown Hotel Chicago

Chinatown
CA $881
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
5.6/10 (1,004 reviews)
Good location close to the downtown, but requires some improvement in room conditions overall.

Reviewed on Aug 27, 2026

Jaslin Hotel

Jaslin Hotel

Chinatown
CA $1,016
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (1,307 reviews)
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Cheap Hotels in South Side

Jaslin Hotel

Jaslin Hotel

261 West Cermak Rd Chicago IL
  • 11 min drive from University of Chicago
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 ...
Jaslin Hotel
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

4900 S Lake Shore Dr Chicago IL
  • 25 min walk from University of Chicago
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)
"Rooms very clean, beds are good, staff is attentive. Terrible wifi reception and since cell reception is bad this is a double whammy. Also no grab and go in the lobby and no cable TV in the rooms. That's a standard everywhere else. We couldn't add our own apps to the TV to stream our preferred networks ..."

Reviewed on Aug 28, 2026

Chicago Lake Shore Hotel
See all 465 properties in South Side
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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $38
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $63
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in South Side

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.