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 $1,012, 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 19 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 23 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 Illinois
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 1 day 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 Illinois
Price found within the past 48 hours. Click for updated prices.
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 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
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 Illinois
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 23 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 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
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)
Clean rooms, great reception, and beautiful views!
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.
