South Side Adventure Holidays
Book a Adventure Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- 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 + Adventure hotel deals in South Side
Price found within the past 48 hours. Click for updated prices.
3 Night Adventure holidays in South Side
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4 Night Adventure holidays in South Side
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Best Western Grant Park Hotel
Downtown Chicago
£976
per person
25 Sept - 29 Sept
found 17 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.2/10 Very good! (2,760 reviews)
The air conditioner was leaking water and made half of the carpet wet and thus the room smelt bad as well.
Reviewed on 6 Aug 2026
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View all tripsTop Adventure South Side Hotels
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
- 11 min drive from University of Chicago
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, 3 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
Best Western Grant Park Hotel
1100 S Michigan Ave Chicago IL
- 14 min drive from University of Chicago
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! (2,760 reviews)
"The air conditioner was leaking water and made half of the carpet wet and thus the room smelt bad as well."
Reviewed on 6 Aug 2026
Jaslin Hotel
261 West Cermak Rd Chicago IL
- 11 min drive from University of Chicago
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! (1,284 reviews)
"Fantastic stay for lollapalooza- only a few train stations away from grant park! super clean and comfortable- definitely will stay again."
Reviewed on 7 Aug 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: Willis Tower Skydeck and The Ledge Ticket
£35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
£18
per adult
90% of travellers recommend
* 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.
