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.
4 Night Cheap holidays in South Side
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Chinatown Hotel Chicago
Chinatown
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
5.4/10 (1,000 reviews)
No frills hotel room with a reasonable price for Chicago and a great location to walk downtown. Also has parking very near for Chinatown at 18.99 for 24 hrs.
Reviewed on Jul. 31, 2025
Jaslin Hotel
Chinatown
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.8/10 Excellent! (1,104 reviews)
Great stay that met our needs. No bells and whistles but clean and friendly staff. We were in town for a basketball tournament and it was an easy 15-20min walk away from hotel. Chinatown across the street made eating options easy, walgreens also across the street for other needs. Overall a good choice if you don't need a poil, hot tub, breakfast options, gym. Starbucks is next door too.
Reviewed on Aug. 7, 2025
Cheap Hotels in South Side
Jaslin Hotel
261 West Cermak Rd, Chicago, IL
Stay at this 3-star hotel in Chicago. Enjoy a 24-hour fitness center, a 24-hour front desk, and premium TV channels. Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,105 reviews)
"Room was comfortable and clean. But wish there was on site parking"
Reviewed on Aug. 7, 2025
Chicago Lake Shore Hotel
4900 S Lake Shore Dr, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the ...
"hotel was about what we expected. Nice breakfast and staff was kind"
Reviewed on Nov. 8, 2023
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.
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