Plan, book, travel with confidence
Better together
Save up to CA $775 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Holiday Package Deals in Downtown Chicago
Price found within the past 48 hours. Click for updated prices.
Ambassador Chicago, part of JdV by Hyatt
Downtown Chicago
Save 100% on your flight
per person
Jul. 29 - Aug. 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
Parking around the hotel is horrible, so they are able to charge an arm and a leg for valet! If you come & go often, then the price is worth is as there is a paid parking lot just a short walk to the corner from the hotel.
Also the restaurant was FREEZING,
Reviewed on May 28, 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 $242 per night from Jun. 5 to Jun. 6
CA $242
CA $284 total
includes taxes & fees
Jun 5 - Jun 6
7.6/10 Good! (6,815 reviews)
"No hot water during whole stay. Had to shower in a fellow traveller's room."
Reviewed on May 27, 2024
River Hotel
75 East Wacker Drive, Chicago, IL
The price is CA $271 per night from Jun. 16 to Jun. 17
CA $271
CA $318 total
includes taxes & fees
Jun 16 - Jun 17
8.6/10 Excellent! (2,900 reviews)
Perfect for a get away weekend
"Hotel was clean, high end, with friendly and helpful staff. The Valet in particular was a kind Italian gentleman who was helpful and informative. Only issue from my end was the “parking” I paid for turned out to be a lot several blocks from the hotel. I chose just to use the valet service but save ..."
Reviewed on May 25, 2024
Eurostars Magnificent Mile
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $273 per night from Jun. 16 to Jun. 17
CA $273
CA $320 total
includes taxes & fees
Jun 16 - Jun 17
8.2/10 Very Good! (1,953 reviews)
Outstanding Front desk staff and Hotel
"Very Nice Hotel, In the heart of Chicago. Friendly and professional staff and the vallet guys are top notch not to mention cool. You are legit in walking distance of some if not all of what Chicago has to offer in terms of touristy type tings."
Reviewed on May 26, 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
Other vacations you might like
Hotels
Best Hotels in Fort McMurrayMagnificent Mile Cheap HotelsHard Rock Hotel Los Cabos All InclusiveHotels in The LoopHotels in Magnificent MileHotels in River NorthHotels in Wicker ParkHotels in Gold CoastLollapalooza hotelsChicago Theatre hotelsGrant Park hotelsGuelph Cheap HotelsMichigan Avenue hotelsMagnificent Mile Hotels with Free ParkingMillennium Park hotelsChicago Riverwalk hotels
Flights
Activities
General
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.