New Chicago Vacation Packages
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Save up to CA $1,096 when you book a flight and hotel together*
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Top New Chicago Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Arlo Chicago
Downtown Chicago
Price was CA $1,302, price is now CA $820 per person
CA $820
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,844 reviews)
This property was clean, lively and convenient to major attractions. The staff. Cleaning crew and front desk were exceptional
Reviewed on Sep. 7, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,903, price is now CA $1,148 per person
CA $1,148
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Location, cleanliness, and friendly staff
Reviewed on Sep. 7, 2025
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was CA $1,352, price is now CA $827 per person
CA $827
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
The staff were very friendly and helpful, and the location in the city is excellent. My only complaint is that the walls are quite thin, so you can easily hear noise from the surrounding rooms.
Reviewed on Sep. 8, 2025
Level Chicago - River North
Downtown Chicago
Price was CA $1,759, price is now CA $1,142 per person
CA $1,142
per person
Oct 24 - Oct 29
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (679 reviews)
Rooms could be updated. Staff was under trained. Amenities very nice, used family room daily with our toddler. Pool deck very modern and new
Reviewed on Sep. 8, 2025
The Langham, Chicago
Downtown Chicago
Price was CA $2,051, price is now CA $1,357 per person
CA $1,357
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug. 12, 2025
New Chicago Hotel Deals
Ameristar Casino Hotel East Chicago
777 Ameristar Blvd., East Chicago, IN
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Sep 9 to Sep 10
CA $135
CA $165 total
Sep 9 - Sep 10
includes taxes & fees
Super 8 by Wyndham South Holland
17225 Halsted St, South Holland, IL
Fully refundableReserve now, pay when you stay
The price is CA $106 per night from Sep 14 to Sep 15
CA $106
CA $120 total
Sep 14 - Sep 15
includes taxes & fees
Fairfield Inn and Suites By Marriott Merrillville
8275 Georgia St, Merrillville, IN
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Sep 14 to Sep 15
CA $128
CA $144 total
Sep 14 - Sep 15
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.
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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.
