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 $2,030, price is now CA $1,293 per person
CA $1,293
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
I loved it. The location was perfect and I specifically pick this hotel based on the view and it did not disappoint. If you don’t wanna go far, there are plenty of restaurants and things to do right around the hotel so that was also convenient. I will definitely be going back.
Reviewed on May 1, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,461, price is now CA $954 per person
CA $954
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great and helpful staff very clean, a place where you don’t feel out of place
Reviewed on Apr 25, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,467, price is now CA $1,649 per person
CA $1,649
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,851 reviews)
Absolutely fantastic will be back
Reviewed on Apr 27, 2026
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See all available trips from Columbus to Central Chicago
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 $2,467, price is now CA $1,649 per person
CA $1,649
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,851 reviews)
Absolutely fantastic will be back
Reviewed on Apr 27, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,783, price is now CA $1,938 per person
CA $1,938
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Wonderful Hotel will definitely be looking forward to going back.
Reviewed on Apr 25, 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.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,131, price is now CA $742 per person
CA $742
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
Great location, nice property, extremely slow breakfast at in house restaurant Toro. Didn’t appreciate paying an “urban experience fee” with associated taxes.
Reviewed on Apr 24, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,836, price is now CA $1,194 per person
CA $1,194
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
I loved it. The location was perfect and I specifically pick this hotel based on the view and it did not disappoint. If you don’t wanna go far, there are plenty of restaurants and things to do right around the hotel so that was also convenient. I will definitely be going back.
Reviewed on May 1, 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.
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,461, price is now CA $954 per person
CA $954
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great and helpful staff very clean, a place where you don’t feel out of place
Reviewed on Apr 25, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,030, price is now CA $1,293 per person
CA $1,293
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
I loved it. The location was perfect and I specifically pick this hotel based on the view and it did not disappoint. If you don’t wanna go far, there are plenty of restaurants and things to do right around the hotel so that was also convenient. I will definitely be going back.
Reviewed on May 1, 2026
Don't see what you're looking for?
See all available trips from Columbus to Central Chicago
View all tripsCheap Hotels in Central Chicago
Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (2,659 reviews)
I recently stayed at Hotel Felix and overall had a decent experience. The location is great and very convenient, and the staff were friendly and welcoming throughout my stay. The room itself was clean and comfortable. The only issue I experienced was mold on the bathroom wall and ceiling. I contacted ...
Reviewed on May 2, 2026
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! (5,150 reviews)
EXCELLENT LOCATION
Reviewed on May 2, 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! (4,246 reviews)
I don’t understand the excellent reviews at this hotel. The hotel was in a great location. However the room was very dated and smelled of mildew and mold. Shower was filthy. Furniture was falling apart. Would not stay here again.
Reviewed on May 2, 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.
