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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,494, price is now CA $986 per person
CA $986
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Terrible attitude of the front desk clerk.
Room smelled bad, dirty carpet.
Reviewed on Jun 24, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,869, price is now CA $1,295 per person
CA $1,295
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) 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 $2,604, price is now CA $1,842 per person
CA $1,842
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) 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
Level Chicago - River North
Downtown Chicago
Price was CA $2,376, price is now CA $1,714 per person
CA $1,714
per person
Aug 3 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.
Reviewed on Jun 19, 2026
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View all trips5* Cheap holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Nobu Hotel Chicago
Downtown Chicago
Price was CA $2,007, price is now CA $1,632 per person
CA $1,632
per person
Aug 5 - Aug 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (869 reviews)
My stay was remarkable! Staff was extremely friendly, room clean, in room dining food was delicious!
Reviewed on Jun 21, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $5,404, price is now CA $3,963 per person
CA $3,963
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
It's a awesome place to stay
Reviewed on Jun 24, 2026
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See all available trips from Ann Arbor to Central Chicago
View all trips3 Night Cheap holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,494, price is now CA $986 per person
CA $986
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Terrible attitude of the front desk clerk.
Room smelled bad, dirty carpet.
Reviewed on Jun 24, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,869, price is now CA $1,295 per person
CA $1,295
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) 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
Omni Chicago Hotel
Downtown Chicago
Price was CA $1,633, price is now CA $1,136 per person
CA $1,136
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) 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
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See all available trips from Ann Arbor to Central Chicago
View all trips4 Night Cheap holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North
Downtown Chicago
Price was CA $1,688, price is now CA $1,099 per person
CA $1,099
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.
Reviewed on Jun 19, 2026
JW Marriott Chicago
Downtown Chicago
Price was CA $1,836, price is now CA $1,244 per person
CA $1,244
per person
Aug 31 - Sep 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,004 reviews)
Good customer service and the food in the lobby restaurants was so good! Also the service at that restaurant is amazing I believe her name was Stephanie, she went out of her way to find me caffeine free Diet Coke. Also, we forgot to tell them that we don’t eat bacon after the hamburger came. They happily to get back and started another hamburger to make sure there’s no bacon residue in it.
Reviewed on May 31, 2026
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See all available trips from Ann Arbor to Central Chicago
View all tripsCheap Hotels in Central Chicago
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! (2,630 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
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! (10,179 reviews)
"Great location for see the city. Staff is very friendly and helpful. The only problem we had was the a/c unit was leaking water on the floor the staff came in the room and turned off the a/c unit and left a fan to help with the summer heat. Parking was expensive but very close to the hotel. Parking ..."
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.
