South Side Cheap Holidays
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- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages 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 £1,346, price is now £1,219 per person
£1,219
per person
10 Sept - 15 Sept
found 1 day ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.2/10 Wonderful! (1,151 reviews)
Very clean for a large hotel. The staff was very helpful when we interacted with them.
It's in a nice neighborhood, It's surprisingly quiet for being in the city.
We will be staying here again.
Reviewed on 29 Jun 2026
4 Night Cheap holidays in South Side
Price found within the past 48 hours. Click for updated prices.
Best Western Grant Park Hotel
Downtown Chicago
Price was £1,494, price is now £1,399 per person
£1,399
per person
8 Aug - 12 Aug
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
8.2/10 Very good! (2,736 reviews)
Not one to complain but the room had a concrete hole in the wall by the windows, went to get a blanket and stopped by the vending machine and had a cockroach crawl on my leg. Don’t know where it came from but it was there. The 2 restaurants were amazing both taste and staff! The hotel staff was super friendly but the building needs updating and cleaning!
Reviewed on 30 Jun 2026
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. Popular attractions Soldier Field and Grant Park are located ...
5.6/10 (1,006 reviews)
"Clean room 1 Shops nearby China"
Reviewed on 29 Jun 2026
Jaslin Hotel
261 West Cermak Rd Chicago IL
Stay at this hotel in Chicago. Enjoy free Wi-Fi, a 24-hour fitness centre and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,237 reviews)
"breakfast is nessary water pot is nessary"
Reviewed on 30 Jun 2026
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 ...
8.2/10 Very good! (2,731 reviews)
"Not one to complain but the room had a concrete hole in the wall by the windows, went to get a blanket and stopped by the vending machine and had a cockroach crawl on my leg. Don’t know where it came from but it was there. The 2 restaurants were amazing both taste and staff! The hotel staff was super ..."
Reviewed on 30 Jun 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.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
£18
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
£30
per adult
94% of travellers recommend
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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.
