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.
The Talbott, Autograph Collection
Downtown Chicago
Price was CA $1,313, price is now CA $936 per person
CA $936
per person
Aug 30 - Sep 3
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (120 reviews)
Always a pleasure and a great location
Reviewed on Jun 24, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $3,614, price is now CA $2,421 per person
CA $2,421
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (493 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,822, price is now CA $2,007 per person
CA $2,007
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
The hotel and location are beautiful but there needs to be much clearer signage as to where the entrance of the hotel is and the main lobby. Extremely confusing to travellers.
Reviewed on Jun 23, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,628, price is now CA $1,936 per person
CA $1,936
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,744 reviews)
Excelente, ubicación perfecta cerca de todo
Reviewed on Jun 23, 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 $2,150, price is now CA $1,647 per person
CA $1,647
per person
Sep 9 - Sep 12
found 6 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
It was everything I expected! The staff was amazing. Everything ran smoothly. I would say the pool could use a little updating. Everything was delightful. Definitely will be back.
Reviewed on Jun 24, 2026
Park Hyatt Chicago
Downtown Chicago
Price was CA $3,311, price is now CA $2,827 per person
CA $2,827
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.6/10 Exceptional! (1,004 reviews)
Excellent hotel and location. 1 min away from Michigan avenue
Reviewed on Jun 23, 2026
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View all trips3 Night Cheap holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel
Downtown Chicago
Price was CA $1,221, price is now CA $904 per person
CA $904
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,813 reviews)
Located in a walkable area near many Chicago attractions. We had a delicious breakfast in the hotel restaurant and the bar is nice. Room was large and comfortable
Reviewed on Jun 23, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,622, price is now CA $1,232 per person
CA $1,232
per person
Sep 9 - Sep 12
found 6 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,134 reviews)
The staff was very welcoming! The bellman greeted us by name the entire trip. Great location for shopping and the riverwalk. Highly recommend!
Reviewed on Jun 23, 2026
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View all trips4 Night Cheap holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,345, price is now CA $1,638 per person
CA $1,638
per person
Aug 14 - Aug 18
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (493 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
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See all available trips from Columbus to Central Chicago
View all tripsCheap Hotels in Central Chicago
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! (10,185 reviews)
"Great price for the hotel itself and location. Parking was affordable and just a block away. Definitely recommend if you are there for an event at Soldier Field or nearby."
Reviewed on Jun 25, 2026
Travelodge by Wyndham Downtown Chicago
65 E Harrison St Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
7.6/10 Good! (2,632 reviews)
"It needs a remodelation , it needs upgrade ,It's a bit neglected. The good thing is the location and downstairs you it has a breakfast restaurant"
Reviewed on Jun 24, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
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 ...
9/10 Wonderful! (4,455 reviews)
"Good location, bar and brunch were great. View from the pool and fitness centers was u real. Room was clean but sink faucet was loose and leaking and the bathroom door locks didn’t work well or would stick. Other than that it was nice."
Reviewed on Jun 24, 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
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Chicago By Night River and Lake Cruise
CA $69
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.
