South Side Waterpark Vacations
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Flight and Waterpark hotel deals in South Side
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago Schaumburg
Price was CA $878, price is now CA $589 per person
CA $589
per person
Nov 9 - Nov 15
just found
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
7.4/10 Good! (1,004 reviews)
Quick stay in between traveling. The bed and bedding comfortable. Room is spacious. Staff friendly.
Reviewed on Aug. 30, 2025
The Langham, Chicago
Downtown Chicago
Price was CA $1,694, price is now CA $1,091 per person
CA $1,091
per person
Nov 11 - Nov 14
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug. 12, 2025
Hilton Chicago O'Hare Airport
O'Hare
Price was CA $891, price is now CA $604 per person
CA $604
per person
Nov 21 - Nov 24
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,103 reviews)
Easy to get to airport but hotel is very tired and outdated
Reviewed on Aug. 29, 2025
Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Price was CA $1,547, price is now CA $1,081 per person
CA $1,081
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,028 reviews)
Overall is good but 1 concern we encountered is there is a clicking sound in our room or near our room, that distracts my husband while sleeping.
Reviewed on Aug. 24, 2025
5* Waterpark holidays in South Side
Price found within the past 48 hours. Click for updated prices.
The Langham, Chicago
Downtown Chicago
Price was CA $1,694, price is now CA $1,091 per person
CA $1,091
per person
Nov 11 - Nov 14
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug. 12, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,564, price is now CA $1,124 per person
CA $1,124
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump
Reviewed on Aug. 29, 2025
Park Hyatt Chicago
Downtown Chicago
Price was CA $1,578, price is now CA $1,199 per person
CA $1,199
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!
Reviewed on Aug. 31, 2025
3 Night Waterpark holidays in South Side
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago O'Hare Airport
O'Hare
Price was CA $891, price is now CA $604 per person
CA $604
per person
Nov 21 - Nov 24
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,103 reviews)
Easy to get to airport but hotel is very tired and outdated
Reviewed on Aug. 29, 2025
The Emily Hotel
Downtown Chicago
Price was CA $1,494, price is now CA $946 per person
CA $946
per person
Nov 11 - Nov 14
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend.
Also the coffee bags ? PERFECTION. Just had to add that
Reviewed on Aug. 22, 2025
The Langham, Chicago
Downtown Chicago
Price was CA $1,694, price is now CA $1,091 per person
CA $1,091
per person
Nov 11 - Nov 14
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug. 12, 2025
4 Night Waterpark holidays in South Side
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was CA $935, price is now CA $531 per person
CA $531
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (1,975 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.
Reviewed on Aug. 25, 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $2,075, price is now CA $1,284 per person
CA $1,284
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.
Reviewed on Aug. 21, 2025
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,541, price is now CA $962 per person
CA $962
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.
Reviewed on Aug. 27, 2025
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