Central Chicago Cheap Vacations
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Flight and Cheap hotel deals in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,305, price is now CA $975 per person
CA $975
per person
Jan 21 - Jan 24
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)
Great
Reviewed on Nov 9, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,344, price is now CA $983 per person
CA $983
per person
Jan 21 - Jan 24
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.
Reviewed on Nov 8, 2026
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View all trips5* Cheap holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,393, price is now CA $1,098 per person
CA $1,098
per person
Jan 21 - Jan 24
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Very good service
Reviewed on Nov 9, 2026
The Langham, Chicago
Downtown Chicago
Price was CA $3,076, price is now CA $2,615 per person
CA $2,615
per person
Dec 16 - Dec 21
found 13 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Valerie at check in was fabulous
Reviewed on Nov 9, 2026
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See all available trips from Columbus to Central Chicago
View all trips3 Night Cheap holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was CA $1,344, price is now CA $983 per person
CA $983
per person
Jan 21 - Jan 24
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.
Reviewed on Nov 8, 2026
Don't see what you're looking for?
See all available trips from Columbus to Central Chicago
View all trips4 Night Cheap holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection
Downtown Chicago
Price was CA $1,880, price is now CA $1,336 per person
CA $1,336
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)
I’ve stayed at Talbott before and enjoyed it, but this time was pretty disappointing! Towel and amenity services were awful and the shower was very poor pressure.
Reviewed on Nov 8, 2026
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View all tripsCheap Hotels in Central Chicago
River Hotel
75 East Wacker Drive Chicago IL
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 ...
8.8/10 Excellent! (5,605 reviews)
"Na"
Reviewed on Nov 9, 2026
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
8.8/10 Excellent! (3,662 reviews)
"My room was clean and everything was exactly as expected. Couldn't check in early, but it happens."
Reviewed on Nov 9, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
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! (10,146 reviews)
"We stayed at the buckinham wing of the hotel. It’s an old hotel. The water runs brown for the first few seconds . The curtains were bright silver. Not what I expected. The best part is the location ."
Reviewed on Nov 9, 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.
Things to do
Skydeck Chicago at Willis Tower
CA $60
per adult
84% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $57
per adult
94% of travellers recommend
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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.
