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
CA $1,374
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
A wonderful hotel. The hotel is in a great location and very convenient. The breakfast is plentiful and delicious
Reviewed on Sep 23, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $932
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,681 reviews)
A beautiful hotel, with amazing views, right on the water! The staff was very friendly and there's plenty to do within walking distance. I would highly recommend.
Reviewed on Sep 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.
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View all trips3 Night Cheap holidays in Central Chicago
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Level Chicago – Old Town
Downtown Chicago
CA $1,047
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
Amazing stay. Love the balcony view. Parking was easy and accessible. Will be back!
Reviewed on Sep 19, 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.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,229
per person
Oct 25 - Oct 29
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
A wonderful hotel. The hotel is in a great location and very convenient. The breakfast is plentiful and delicious
Reviewed on Sep 23, 2026
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View all tripsCheap Hotels in Central Chicago
River Hotel
75 East Wacker Drive Chicago IL
- 6 min drive from McCormick Place
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 ...
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
- 4 min drive from McCormick Place
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! (10,192 reviews)
"I’ve stayed here for years. Every riot"
Reviewed on Sep 22, 2026
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
- 6 min drive from McCormick Place
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
9/10 Wonderful! (2,911 reviews)
"Great hotel in a super location. We had a room with a living area which was lovely. Wish they had coffee all day and not just until 10/11’ish We will stay there again"
Reviewed on Sep 22, 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
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% 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.
