Washington Heights Vacation Packages
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Top Holiday Package Deals in Washington Heights
Price found within the past 48 hours. Click for updated prices.
Stay One Chicago
Downtown Chicago
Price was CA $3,061, price is now CA $2,385 per person
CA $2,385
per person
Apr 28 - May 4
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
No reviews
The property was great, the room was awesome! The "Stay One Chicago" is really just a name on paper, and maybe one employee who is physically at the property. I am pretty sure that he wasn't even directly employed by the "hotel".
So in a nutshell, the organization has not worked out any kind of structure for checking in other than the guy that told us to download the Door, OR the Latch app. He said that the app is very difficult to get logged into.
Long story made short, we wasted the 1st 2 hours in the hotel trying to get the app (both my wife and I).
The app never worked, and we finally got physical key cards from the guy working for the building.
There was one small piece of paper with scan codes for restaurants, but zero property maps, rules, room cleaning, and nothing explaining how to get to, or use any of the amenities. It was the worst 1st 3 hours of a vacation that we have experienced.
I still gave it a 4-star because the local people were so nice and helpful, even though helping us wasn't part of their job. The valet guys were the best, super nice, and helpful.
Reviewed on Feb 10, 2026
Hyatt Regency Chicago
Downtown Chicago
Price was CA $926, price is now CA $723 per person
CA $723
per person
Apr 3 - Apr 6
found 3 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (3,386 reviews)
The room was amazing! Staff was friendly and itbis in a very good location.
Reviewed on Feb 13, 2026
Where to stay in Washington Heights
Find the best Washington Heights areas and neighborhoods for the activities you enjoy most. Learn more about Washington Heights
Downtown Chicago
4 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Washington Heights Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from Feb 16 to Feb 17
CA $121
CA $143 total
Feb 16 - Feb 17
includes taxes & fees
8/10 Very Good! (9,872 reviews)
Room was nice and clean. Hotel had a fantastic classic look and feel. Perfect place to stay for shows at the Auditorium theater across the street. It's a very old building so the heating and hot water situation is a little off compared to newer hotels but nothing that would deter me from staying ...
Reviewed on Feb 13, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Mar 4 to Mar 5
CA $154
CA $219 total
Mar 4 - Mar 5
includes taxes & fees
9.2/10 Wonderful! (3,323 reviews)
Friendly staff, tasteful room
Reviewed on Feb 11, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $189 per night from Feb 21 to Feb 22
CA $189
CA $261 total
Feb 21 - Feb 22
includes taxes & fees
8.4/10 Very Good! (2,618 reviews)
It was great
Reviewed on Feb 12, 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.
Frequently asked questions
Discover the most popular places to visit in Washington Heights
Michigan Avenue
4.5/5(19 reviews)
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Wrigley Field
4.5/5(158 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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
Wendella's 90-min Chicago River Architecture Tour
CA $55
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.