Illinois Adventure Vacations
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Flight and Adventure hotel deals in Illinois
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was CA $1,045, price is now CA $837 per person
CA $837
per person
Mar 13 - Mar 15
found 8 hours ago
Roundtrip flight included
Montreal (YMQ) 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 1 day 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
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,482, price is now CA $1,135 per person
CA $1,135
per person
Apr 14 - Apr 18
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Clean rooms, great reception, and beautiful views!
Reviewed on Feb 10, 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 1 day 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
5* Adventure holidays in Illinois
Price found within the past 48 hours. Click for updated prices.
3 Night Adventure holidays in Illinois
Price found within the past 48 hours. Click for updated prices.
Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Price was CA $969, price is now CA $792 per person
CA $792
per person
Mar 13 - Mar 16
found 9 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (1,034 reviews)
All good. bar staff was not that friendlly
Reviewed on Feb 3, 2026
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
Price was CA $1,200, price is now CA $979 per person
CA $979
per person
Mar 13 - Mar 16
found 9 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (2,558 reviews)
Clean room, professional staff and location
Reviewed on Feb 9, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,319, price is now CA $1,085 per person
CA $1,085
per person
Mar 13 - Mar 16
found 1 day 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
4 Night Adventure holidays in Illinois
Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,482, price is now CA $1,135 per person
CA $1,135
per person
Apr 14 - Apr 18
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Clean rooms, great reception, and beautiful views!
Reviewed on Feb 10, 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 1 day 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
Adventure Hotels in Illinois
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
The price is CA $182 per night from Feb 21 to Feb 22
CA $182
CA $248 total
Feb 21 - Feb 22
includes taxes & fees
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
The price is CA $256 per night from Feb 13 to Feb 14
CA $256
CA $333 total
Feb 13 - Feb 14
includes taxes & fees
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
The price is CA $236 per night from Feb 22 to Feb 23
CA $236
CA $317 total
Feb 22 - Feb 23
includes taxes & fees
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.
