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Top Holiday Package Deals in Downtown Chicago
Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel
Downtown Chicago
per person
Aug. 15 - Aug. 18
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,253 reviews)
The hotel was great! Check in was smooth, staff was wonderful and the breakfast was good! Really enjoyed the hotel, definitely will stay again!
Reviewed on May 22, 2024
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug. 15 - Aug. 18
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,190 reviews)
I loved our stay. The view was unbelievable. The tub was the only concern, it was leaking the water out from the drain area so i had to use more water. That was not a tragedy but just so you guys know it could use a small fix.
Reviewed on May 22, 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 $226 per night from May 27 to May 28
CA $226
CA $265 total
includes taxes & fees
May 27 - May 28
7.6/10 Good! (6,786 reviews)
"Nice old hotel with a lot of history, in a beautiful area in sight of Lake Michigan."
Reviewed on May 22, 2024
River Hotel
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $220 per night from May 27 to May 28
CA $220
CA $258 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
Warwick Allerton - Chicago
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $171 per night from May 27 to May 28
CA $171
CA $221 total
includes taxes & fees
May 27 - May 28
7.6/10 Good! (2,602 reviews)
"I don’t really write reviews for places I stay at but this one impressed me beyond my expectations. I planned this trip for my fiancé’s 30th birthday and the location and price of this hotel is the best you will find. Not too far away from everything, conveniently located transportation and so many ..."
Reviewed on May 20, 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.