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 Riu Plaza Chicago
Downtown Chicago
Price was CA $1,634, price is now CA $1,131 per person
CA $1,131
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Everything was great, except for the rooftop that was not open because which was the main reason we chose this hotel
Reviewed on Mar 10, 2026
Hotel Arista
Price was CA $1,217, price is now CA $946 per person
CA $946
per person
May 24 - May 29
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Room was clean, staff was friendly and parking was really easy. Very comfortable stay.
Reviewed on Mar 5, 2026
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View all trips5* Cheap holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $1,760, price is now CA $1,406 per person
CA $1,406
per person
Apr 23 - Apr 26
found 16 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Nice bellmen, nice front staff, rooms were cozy and well kept. Everyone was very friendly and helpful. We would stay again.
Reviewed on Mar 1, 2026
The Peninsula Chicago
Downtown Chicago
Price was CA $2,230, price is now CA $1,808 per person
CA $1,808
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
This is an amazing hotel. From the facilities to the staff, the food and atmosphere and the intricacies of the room itself it’s an amazing property. In the heart of what used to be “The magnificent mile” it’s unimposing from the exterior but once you step inside the place is special. If you can afford it it’s probably the best hotel in Chicago. Do yourself a favor and splurge a little on a weekend trip. Chicago is a wonderful city for food and drinks. It’s seen better days but still a beautiful city.
Reviewed on Mar 10, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,011, price is now CA $1,644 per person
CA $1,644
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,839 reviews)
One of the best hotels I've ever stayed at
Reviewed on Mar 10, 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.
Hilton Chicago O'Hare Airport
O'Hare
Price was CA $1,091, price is now CA $853 per person
CA $853
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (2,220 reviews)
We only stayed because we had to make a connection in the morning and it is the hotel attached to the airport
Reviewed on Mar 10, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,634, price is now CA $1,131 per person
CA $1,131
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Everything was great, except for the rooftop that was not open because which was the main reason we chose this hotel
Reviewed on Mar 10, 2026
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Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,178, price is now CA $829 per person
CA $829
per person
Apr 27 - May 1
found 11 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Everything was great, except for the rooftop that was not open because which was the main reason we chose this hotel
Reviewed on Mar 10, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,750, price is now CA $1,161 per person
CA $1,161
per person
May 13 - May 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (414 reviews)
This place was amazing! We loved it so much we wanted to move in. It had everything we needed and was in the perfect area. Parker at the front desk was by far the best part of our stay, she was personable and welcoming and gave us the best costumer service we’ve ever experienced while being away! We will be back.
Reviewed on Mar 8, 2026
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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! (9,942 reviews)
I like this hotel. It’s simple, clean, no frills and gets the job done. Hallways carpets are a little worse for wear but the room serves the purpose - you get what you reserve! - and you’re close to everything. It’s a “go to” for me.
Reviewed on Mar 10, 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! (3,895 reviews)
Clean room - great staff - would stay here again!
Reviewed on Mar 11, 2026
Eurostars Magnificent Mile
660 North State Street Chicago IL
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (3,294 reviews)
I stayed in the pano room in the 25th floor. Bed was super uncomfortable, but views and room was amazing.
Reviewed on Mar 11, 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.
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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.
