South Side Cheap Holidays
Book a Cheap Hotel + Flight or Car together to unlock savings
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Better together
Save up to £335 when you book a flight and hotel together*
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With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Packages with flights are ATOL protected
Top flight + 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
Price was £1,113, price is now £1,070 per person
£1,070
per person
10 Oct - 13 Oct
found 9 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,033 reviews)
From the time we walked in the doors to leaving this morning ALL staff, front desk, housekeeping, Starbucks/Market, etc were all friendly, courteous, and helpful!
Reviewed on 6 Sep 2025
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
Price was £1,113, price is now £1,070 per person
£1,070
per person
10 Oct - 13 Oct
found 9 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,033 reviews)
From the time we walked in the doors to leaving this morning ALL staff, front desk, housekeeping, Starbucks/Market, etc were all friendly, courteous, and helpful!
Reviewed on 6 Sep 2025
4 Night Cheap holidays in South Side
Price found within the past 48 hours. Click for updated prices.
Top Cheap South Side Hotels
Chinatown Hotel Chicago
214 West 22nd Place, Chicago, IL
Stay at this hotel in Chicago. Enjoy free Wi-Fi, a 24-hour front desk and daily housekeeping. Our guests praise the property condition in their reviews. Popular ...
Jaslin Hotel
261 West Cermak Rd, Chicago, IL
Stay at this 3-star hotel in Chicago. Enjoy a 24-hour fitness centre, a 24-hour front desk and premium TV channels. Our guests praise the helpful staff and the ...
Best Western Grant Park Hotel
1100 S Michigan Ave, Chicago, IL
Stay at this hotel in Chicago. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
