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Top Holiday Package Deals in Downtown Chicago
Prices and availability subject to change. Additional terms may apply.
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul. 10 - Jul. 15
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (965 reviews)
Friendly and helpful staff, super comfy rooms and bed! Walked everywhere- easy walk to museum/aquarium, shopping, dining etc. will definitely be back!
Reviewed on Apr. 15, 2024
JW Marriott Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul. 11 - Jul. 14
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The staff were welcoming, courteous, and friendly. The location was perfect and room was beautiful and clean!
Reviewed on Apr. 14, 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 $167 per night from Apr. 28 to Apr. 29
CA $167
CA $196 total
includes taxes & fees
Apr 28 - Apr 29
7.6/10 Good! (6,584 reviews)
"Good location"
Reviewed on Apr. 21, 2024
River Hotel
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $181 per night from Apr. 28 to Apr. 29
CA $181
CA $212 total
includes taxes & fees
Apr 28 - Apr 29
8.6/10 Excellent! (2,808 reviews)
"The room wasn't done during my stay"
Reviewed on Apr. 22, 2024
Eurostars Magnificent Mile
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $219 per night from Apr. 28 to Apr. 29
CA $219
CA $257 total
includes taxes & fees
Apr 28 - Apr 29
8.2/10 Very Good! (1,853 reviews)
"When we booked with Hotels it said our room would have a balcony and it didnt. It also said it had roof top outdoor sitting and it was closed also. If it had said it wasn't opened to sit up there or the balconies we couldnt use i would not of booked with that hotel."
Reviewed on Apr. 22, 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
Chicago Architecture Center River Cruise aboard Chicago's First Lady
CA $73
Per adult
92% of travellers recommend
Chicago Pizza Tour
CA $102
Per adult
100% of travellers recommend
Chicago Museum of Contemporary Art: General Admission Ticket
CA $30
Per adult
90% of travellers recommend
Other vacations you might like
Hotels
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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.