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Top Holiday Package Deals in Downtown Chicago
Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug. 15 - Aug. 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
We celebrated a bachelorette party and stayed at this hotel. They were very accommodating to my requests and even greeted us with a welcome present! It made our stay that much better! Would definitely recommend this hotel.
Reviewed on May 22, 2024
Pendry Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul. 4 - Jul. 8
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (687 reviews)
This is probably the very best location to stay when visiting Chicago. A beautiful old Art Deco building that has been beautifully maintained. We loved staying here. Easy walk to everything.
Reviewed on May 25, 2024
Where to stay in Downtown Chicago
Find the best Downtown Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Downtown 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.
Downtown Chicago Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $203 per night from May 27 to May 28
CA $203
CA $238 total
includes taxes & fees
May 27 - May 28
7.6/10 Good! (6,802 reviews)
"No parking available"
Reviewed on May 24, 2024
River Hotel
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from May 27 to May 28
CA $193
CA $227 total
includes taxes & fees
May 27 - May 28
8.6/10 Excellent! (2,886 reviews)
"Appreciated the easy of self serve check in and checkout. Did not have to stand in line. Only complaint is that the wait time for elevators is too long. Number iof elevators do not support number of guests"
Reviewed on May 22, 2024
Eurostars Magnificent Mile
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $246 per night from May 29 to May 30
CA $246
CA $289 total
includes taxes & fees
May 29 - May 30
8.2/10 Very Good! (1,939 reviews)
"Great service. Guy at front desk was extremely friendly and got us checked in three hours early and gave us a complimentary room upgrade. The room was amazing. It was a corner room with floor to ceiling windows. Great view. The bed was comfortable and the shower is huge with great water pressure. ..."
Reviewed on May 21, 2024
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.
Explore other types of vacation packages
Frequently asked questions
Discover the most popular places to visit in Downtown Chicago
Navy Pier
4.5/5(459 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Grant Park
4.5/5(291 reviews)
Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.
Millennium Park
4.5/5(722 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Things to do
Odyssey Lake Michigan Premier Dinner Cruise
CA $311
Per adult
76% of travellers recommend
Chicago Pizza Tour
CA $102
Per adult
100% of travellers recommend
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Flights
Activities
General
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.