Uptown Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Uptown
Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
Save 100% on your flight
Price was CA $1,343, price is now CA $820 per person
CA $820
per person
Jan 2 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)
The staff is very friendly and professional.
Reviewed on Oct 27, 2026
Sheraton Grand Chicago Riverwalk
Downtown Chicago
Save 100% on your flight
Price was CA $1,702, price is now CA $823 per person
CA $823
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)
Thank you so much for a wonderful experience.
Reviewed on Oct 27, 2026
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was CA $1,523, price is now CA $1,004 per person
CA $1,004
per person
Jan 2 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,572 reviews)
Hotel smells amazing
Reviewed on Oct 28, 2026
Uptown Hotel Deals
La Quinta Inn & Suites by Wyndham Chicago Gurnee
5688 Northridge Rd Gurnee IL
Fully refundableReserve now, pay when you stay
The price is CA $92 per night from Nov 2 to Nov 3
CA $92
CA $103 total
Nov 2 - Nov 3
includes taxes & fees
The Inn on Sheridan
2723 Sheridan Rd Zion IL
Fully refundableReserve now, pay when you stay
The price is CA $103 per night from Nov 16 to Nov 17
CA $103
CA $114 total
Nov 16 - Nov 17
includes taxes & fees
Great Wolf Lodge Illinois
1700 Nations Dr Gurnee IL
The price is CA $218 per night from Oct 29 to Oct 30
CA $218
CA $248 total
Oct 29 - Oct 30
includes taxes & fees
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.