Cheap Vacations in South Side 2026

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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

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

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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4 Night Cheap holidays in South Side

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

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

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

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 ...

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

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.