Illinois Cheap Vacations
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Flight and Cheap hotel deals in Illinois
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $600, price is now CA $502 per person
CA $502
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
There were no glasses in the room to drink out of. There was no lotion. There was no coffee maker. The shower curtain does not stretch the whole way so water gets all over the bathroom. We had a free VIP "hot" breakfast. When went down, there was no hot food. Just coffee and some bakery items. And no employee to serve us. Very, very misleading. We won't be staying here again.
Reviewed on Feb 2, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was CA $844, price is now CA $725 per person
CA $725
per person
Mar 15 - Mar 19
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (1,769 reviews)
Loved the location. And the staff was very accommodating.
Reviewed on Feb 4, 2026
Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
Price was CA $581, price is now CA $517 per person
CA $517
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.8/10 Excellent! (3,289 reviews)
The staff was very helpful with the check in and the room was great.
Reviewed on Jan 29, 2026
River Hotel
Downtown Chicago
Price was CA $617, price is now CA $571 per person
CA $571
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.8/10 Excellent! (4,800 reviews)
family room includes 2 rooms without doors, living room and only 1 window, and that comes back. Well, in general, the room is clean, there is an electric stove, oven, sink, overall everything for comfort is in room except Windows.
Reviewed on Feb 2, 2026
3 Night Cheap holidays in Illinois
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $768, price is now CA $642 per person
CA $642
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
There were no glasses in the room to drink out of. There was no lotion. There was no coffee maker. The shower curtain does not stretch the whole way so water gets all over the bathroom. We had a free VIP "hot" breakfast. When went down, there was no hot food. Just coffee and some bakery items. And no employee to serve us. Very, very misleading. We won't be staying here again.
Reviewed on Feb 2, 2026
Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
Price was CA $778, price is now CA $688 per person
CA $688
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Chicago (ORD)
8.8/10 Excellent! (3,289 reviews)
The staff was very helpful with the check in and the room was great.
Reviewed on Jan 29, 2026
4 Night Cheap holidays in Illinois
Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was CA $844, price is now CA $725 per person
CA $725
per person
Mar 15 - Mar 19
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (1,769 reviews)
Loved the location. And the staff was very accommodating.
Reviewed on Feb 4, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,382, price is now CA $1,138 per person
CA $1,138
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
There were no glasses in the room to drink out of. There was no lotion. There was no coffee maker. The shower curtain does not stretch the whole way so water gets all over the bathroom. We had a free VIP "hot" breakfast. When went down, there was no hot food. Just coffee and some bakery items. And no employee to serve us. Very, very misleading. We won't be staying here again.
Reviewed on Feb 2, 2026
Cheap Hotels in Illinois
River Hotel
75 East Wacker Drive Chicago IL
The price is CA $96 per night from Feb 15 to Feb 16
CA $96
CA $113 total
Feb 15 - Feb 16
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (4,987 reviews)
family room includes 2 rooms without doors, living room and only 1 window, and that comes back. Well, in general, the room is clean, there is an electric stove, oven, sink, overall everything for comfort is in room except Windows.
Reviewed on Feb 2, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
The price is CA $122 per night from Feb 9 to Feb 10
CA $122
CA $143 total
Feb 9 - Feb 10
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (9,863 reviews)
Good location for many activities. Room was good but less than great.
Reviewed on Feb 7, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
The price is CA $133 per night from Feb 15 to Feb 16
CA $133
CA $157 total
Feb 15 - Feb 16
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (3,783 reviews)
Such great service, room was clean, and hotel staff were amazing! 10/10 recommend and will be staying here again when we come back!
Reviewed on Feb 4, 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.
