
Chicago Adventure Vacations
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Flight and Adventure hotel deals in Chicago
Price found within the past 48 hours. Click for updated prices.

Pendry Chicago
Downtown Chicago
Price was CA $1,012, price is now CA $816 per person
CA $816
per person
Apr 13 - Apr 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on Jan 31, 2026

Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Price was CA $1,478, price is now CA $1,085 per person
CA $1,085
per person
Apr 16 - Apr 21
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,034 reviews)
All good. bar staff was not that friendlly
Reviewed on Feb 3, 2026

Hyatt Regency Chicago
Downtown Chicago
Price was CA $1,655, price is now CA $1,312 per person
CA $1,312
per person
Apr 14 - Apr 18
found 20 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (3,386 reviews)
Spacious and clean room but improvement points on amenities (missing tissue in tissue casing, need to call for amenities, nondairy milk available but not dairy milk, dirty coffee maker cannot make tea), dark, and separate towers inconvenient with friends & availability of lifts during conference season low. Road works and access by car/cab not warned
Reviewed on Feb 10, 2026


Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $1,056, price is now CA $857 per person
CA $857
per person
Apr 13 - Apr 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
Joyce and Jean really made my stay at the Chicago Athletic Association one of the most stellar experiences I’ve ever had. They both went above and beyond to make sure I had whatever I needed and the attentiveness for the staff at large was impeccable. Check-in was a breeze and from there the accommodations were top-tier. The room was wonderfully appointed, and the hotel amenities could not be beaten. I will always come back to this hotel.
Reviewed on Jan 5, 2026
5* Adventure holidays in Chicago
Price found within the past 48 hours. Click for updated prices.


The Ritz-Carlton, Chicago
Downtown Chicago
Price was CA $2,940, price is now CA $2,749 per person
CA $2,749
per person
Apr 12 - Apr 18
found 24 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
Great location, service, and gym
Reviewed on Jan 24, 2026
3 Night Adventure holidays in Chicago
Price found within the past 48 hours. Click for updated prices.

The Royal Sonesta Chicago Downtown
Downtown Chicago
Price was CA $734, price is now CA $595 per person
CA $595
per person
Apr 12 - Apr 15
found 16 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.4/10 Exceptional! (3,062 reviews)
Fantastic stay! Will be a return customer when in chicago
Reviewed on Feb 10, 2026

Pendry Chicago
Downtown Chicago
Price was CA $1,466, price is now CA $1,106 per person
CA $1,106
per person
Mar 12 - Mar 15
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on Jan 31, 2026

Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $1,056, price is now CA $857 per person
CA $857
per person
Apr 13 - Apr 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
Joyce and Jean really made my stay at the Chicago Athletic Association one of the most stellar experiences I’ve ever had. They both went above and beyond to make sure I had whatever I needed and the attentiveness for the staff at large was impeccable. Check-in was a breeze and from there the accommodations were top-tier. The room was wonderfully appointed, and the hotel amenities could not be beaten. I will always come back to this hotel.
Reviewed on Jan 5, 2026
4 Night Adventure holidays in Chicago
Price found within the past 48 hours. Click for updated prices.

Hyatt Regency Chicago
Downtown Chicago
Price was CA $1,655, price is now CA $1,312 per person
CA $1,312
per person
Apr 14 - Apr 18
found 20 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (3,386 reviews)
Spacious and clean room but improvement points on amenities (missing tissue in tissue casing, need to call for amenities, nondairy milk available but not dairy milk, dirty coffee maker cannot make tea), dark, and separate towers inconvenient with friends & availability of lifts during conference season low. Road works and access by car/cab not warned
Reviewed on Feb 10, 2026

Pendry Chicago
Downtown Chicago
Price was CA $1,919, price is now CA $1,437 per person
CA $1,437
per person
Mar 12 - Mar 16
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on Jan 31, 2026

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,040, price is now CA $1,575 per person
CA $1,575
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
The room was in pretty good condition. Not as grand as it seems. The carpet was a bit muggy and kind of a weird smell. Bathroom supplies i thought was a bit messy since shampoo was pepermint, conditioner cilantro, and body wash rum... Sounds like ingredients for a drink. The front desk staff not as welcoming. The housekeeper on our floor (9) on the other hand was extremly friendly and helpful and we loved her. Always asking if we needed anything and made us feel great.
Reviewed on Feb 10, 2026
Adventure Hotels in Chicago

Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.4/10 Very Good! (2,280 reviews)
Clean room, checking in was super easy. Hotel is beautiful and so classy.
Reviewed on Feb 7, 2026

Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,067 reviews)
I love the remodel of the rooms Very clean. Friendly staff.
Reviewed on Feb 9, 2026

Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (3,459 reviews)
Clean room, professional staff, and great location
Reviewed on Feb 3, 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.
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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.







