South Side Adventure Holidays
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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
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Packages with flights are ATOL protected
Top flight + Adventure hotel deals in South Side
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3 Night Adventure holidays in South Side
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4 Night Adventure holidays in South Side
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View all tripsTop Adventure South Side Hotels
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr, Chicago, IL
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free Wi-Fi, 3 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,006 reviews)
Overall enjoyable stay, with event at Soldier Fie
"Good place to stay for a Concert at Soldier Field. By in large not bad, comfortable bed. Bathroom could have used a spot more cleaning,. Parking was not the best. Their parking lot was full, and no Valet parking. Had to park in Convention Center parking garage, with about a 15 min walk back to the ..."
Reviewed on 10 Jul 2025
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 ...
8/10 Very Good! (2,561 reviews)
"Staff was friendly and helpful but the room was a bit dated and it had some wear and tear. Location was excellent though"
Reviewed on 13 Jul 2025
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 ...
8.8/10 Excellent! (1,083 reviews)
"This property is conveniently located to all of the places I was there for. It does not have parking. It does not have valet. There’s a parking structure a couple of blocks away. Now for the room… The toilet does not flush properly. The toilet had low pressure. The water would go down but not remove ..."
Reviewed on 13 Jul 2025
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.