Central Chicago Vacation Packages
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Top Central Chicago Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,113, price is now CA $1,436 per person
CA $1,436
per person
Aug 24 - Aug 28
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place.
Reviewed on Jul 14, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was CA $1,178, price is now CA $800 per person
CA $800
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very good! (2,006 reviews)
I wish the space was bigger. It was too tight for me and my young girls but the staff was so extra nice and welcoming.
Reviewed on Jul 14, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,920, price is now CA $1,335 per person
CA $1,335
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We booked a two bedroom unit, but the unit clearly wasn't intended for a 2 bedroom. It was obviously a sitting area or something with a bed squeezed in. There was no vent so it made it impossible to shut the door, but then it was open to the living space and a full wall of windows.
In addition, they list housekeeping as an amenity, and advertise one day or long term stays, however, for our 4 night stay, this didn't get housekeeping services. Meaning we had to get towels and coffee each day from the front desk, had piles of trash from cooking and such, and a heap of dirty towels from the week.
Staff was friendly, but not really provided agency or capacity to do anything to fix the experience. Even a request for a fan to try to cool the space was impossible for them to solve (although they certainly had one for the front desk to keep staff comfortable).
Reviewed on Jul 14, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,339, price is now CA $965 per person
CA $965
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Free beer no perfect everyone was great
Reviewed on Jul 15, 2026
Where to stay in Central Chicago
Find the best Central Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Central Chicago
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
Central Chicago Hotel Deals
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $216 per night from Jul 27 to Jul 28
CA $216
CA $257 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very good! (1,745 reviews)
"Staff wasn’t welcoming or helpful. Hot water in shower didn’t work properly."
Reviewed on Jul 15, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $330 per night from Jul 26 to Jul 27
CA $330
CA $440 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (1,913 reviews)
"Staff was fantastic and always ready to help; from the front door to the room door!"
Reviewed on Jul 15, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $266 per night from Aug 10 to Aug 11
CA $266
CA $316 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very good! (10,264 reviews)
"No parking at hotel. Had to park 5 blocks away and carry bags."
Reviewed on Jul 15, 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.
What to do in Central Chicago
Chicago: Navy Pier Centennial Wheel Ticket
CA $35
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $64
per adult
94% of travellers recommend
Frequently asked questions
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- All Inclusive Resorts and in Chicago
- Flights from O'Hare Intl.
- Flights from Toronto (YYZ) to Chicago (ORD)
- Flights from Regina (YQR) to Chicago (ORD)
- Flights from Halifax (YHZ) to Chicago (ORD)
- Flights from Seattle (SEA) to Chicago (ORD)
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- Flights from Winnipeg (YWG) to Chicago (ORD)
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- Flights from Hamilton (YHM) to Chicago (ORD)
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- Ernest Hemingway Museum and House
- Rosemont Vacations
- Art Institute of Chicago
- Downtown Chicago Vacations
- Visit Magnificent Mile
- Millennium Park
- United Center
- Unity Temple
- Visit The Loop
- Willis Tower
- International Museum of Surgical Science
- Buckingham Fountain
- Montrose Beach
- Golf Vacations
- All inclusive Vacation Packages Chicago
- Lincoln Park Zoo
- Grant Park
- Chicago Vacations
- Griffin Museum of Science and Industry
- Water Tower Place
- 875 North Michigan Avenue
- The Loop Vacations
- Ann and Robert H. Lurie Children's Hospital
- Lakeview Vacations
- Garfield Park Conservatory
- Frank Lloyd Wright Historic District
- Chicago Riverwalk
- Visit Downtown Chicago
- Wrigley Field
- Visit Chicago
- Robie House
- Navy Pier
- Northwestern University
- Chicago Theatre
- Marina City
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
