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.
Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Price was CA $1,599, price is now CA $1,158 per person
CA $1,158
per person
Apr 14 - Apr 19
found 24 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9/10 Wonderful! (1,034 reviews)
Connecting to Northwestern Hospital was the greatest thing ever
Reviewed on Feb 11, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,799, price is now CA $1,377 per person
CA $1,377
per person
Apr 14 - Apr 19
found 24 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
I loved my stay at LondonHouse. I’ll definitely be staying at Curio Collection from now on.
Reviewed on Feb 12, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,431, price is now CA $1,104 per person
CA $1,104
per person
Mar 14 - Mar 18
found 24 hours ago
Roundtrip non-stop 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 Regency Chicago
Downtown Chicago
Price was CA $1,931, price is now CA $1,502 per person
CA $1,502
per person
Apr 14 - Apr 19
found 24 hours ago
Roundtrip flight included
Detroit (DTW) 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
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 $1,744, price is now CA $1,569 per person
CA $1,569
per person
Mar 14 - Mar 18
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) 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.
Pendry Chicago
Downtown Chicago
Price was CA $883, price is now CA $663 per person
CA $663
per person
Mar 15 - Mar 18
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 Regency Chicago
Downtown Chicago
Price was CA $1,349, price is now CA $1,106 per person
CA $1,106
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) 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
4 Night Adventure holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was CA $1,431, price is now CA $1,104 per person
CA $1,104
per person
Mar 14 - Mar 18
found 24 hours ago
Roundtrip non-stop 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 $1,490, price is now CA $1,172 per person
CA $1,172
per person
Mar 14 - Mar 18
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
I loved my stay at LondonHouse. I’ll definitely be staying at Curio Collection from now on.
Reviewed on Feb 12, 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! (3,468 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 ...
Reviewed on Feb 10, 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.
