Washington Heights Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in Washington Heights

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,737, price is now CA $1,169 per person
CA $1,169
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The good: Staff was great Location Comfortable bed The bad: Extra daily charge that you are told about as you check in. I'm sure it's in the fine print but I saw nothing special that extra cost (6 nights it added up) got the guests and I think that's a real insult when we already paying a lot of $$. Water pressure and heat of water terrible. TV didn't work very well Not much in room - small, no fridge, no microwave I'd stay again in a pinch but will avoid - especially because of the inexplicable daily fee.

Reviewed on Jul 11, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,824, price is now CA $1,274 per person
CA $1,274
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Location

Reviewed on Jul 10, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,861, price is now CA $1,332 per person
CA $1,332
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Perfect location Perfect view excellent staff fun time had by wife for her birthday great little getaway thanks

Reviewed on Jul 11, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,693, price is now CA $1,216 per person
CA $1,216
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!

Reviewed on Jul 8, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $3,029, price is now CA $2,213 per person
CA $2,213
per person
Sep 21 - Sep 28
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.

Reviewed on Jul 9, 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
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

5 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.

Find hotels in Downtown Chicago

Washington Heights Hotel Deals

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $218 per night from Jul 27 to Jul 28
CA $218
CA $259 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very good! (1,734 reviews)
"Surprise fees upfront when you book with third party sites like, Expedia. Expect to cough up a few hundred dollars before you even get to the elevator. Other than that it’s a gorgeous hotel with incredible surrounding areas. Not too far from the beach as well. The breakfast buffet was also ..."

Reviewed on Jul 11, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $316 per night from Jul 26 to Jul 27
CA $316
CA $422 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (1,906 reviews)
"Great location and a friendly staff made this a great experience. The rooms are very nice, but a little dated, which made it feel a little less clean. The staff was amazing, especially the doorman/bellman, Ham. He went out of his way help everytime we arrived or departed, he asked how our day was ..."

Reviewed on Jul 11, 2026

Omni Chicago Hotel
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $268 per night from Aug 10 to Aug 11
CA $268
CA $318 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very good! (10,226 reviews)
"We’ve stayed there twice and probably will again."

Reviewed on Jul 11, 2026

Congress Plaza Hotel
See all 4,226 properties in Washington Heights
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Frequently asked questions

How much does a Washington Heights vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Washington Heights from just CA $1,169. And the more you bundle, the more cash you save. The vacation of your dreams has never been more affordable.
How do I get a cheap travel package to Washington Heights?
Bundle your flights and hotels, throw in extras such as tours, and save with a Washington Heights vacation package. You won't just walk away with amazing discounts on your escape — you'll have plenty of choice at your fingertips too. When you book with Expedia, you can select from more than 550 airlines and 1,000,000 hotels globally. Your unforgettable vacation begins right here, right now!
Where should I stay in Washington Heights?
You'll want to stay where the action is. Many visitors like to book hotels around top attractions, such as Dr. Percy Julian Residence, Highland Community Bank and Carter G. Woodson Library.
How far in advance should I book my Washington Heights vacation?
While not all airlines advertise ticket prices early, customers are usually able to start comparing international fares on Expedia up to a year in advance. This is the time you can bag some incredible bargains. If you're booking late, you might get lucky. Sometimes the cheapest prices appear just weeks prior to departure.
What does an Expedia Washington Heights travel package include?
That depends entirely on you. You can pick from a range of Washington Heights bundles, such as a flight, hotel and rental car. You can also book a flight and a hotel, or a rental car with a flight. Once you've made your booking, you can add on the fun stuff like activities and experiences. Whatever your dream Washington Heights escape looks like, get ready to save!
What should I know before booking a Washington Heights travel package?
So many places to wander around, so many things to do. With a travel package, you can check more of them off your list. Bundle your hotels, rental cars and flights and make big savings.
Can I choose my airline with a Washington Heights Expedia vacation package?
Expedia offers access to more than 550 partner airlines globally, so you sure can! Simply select the airline you want and put together your ideal Washington Heights trip.
If I'm not able to travel, can I cancel my Washington Heights vacation package?
If your travel plans in Washington Heights have changed, it's a relief to know that you can amend or cancel your booking. If you made your booking within the last 24 hours, you may be able to receive a refund. If your booking is older than that, your airline, hotel or car rental company may charge a cancellation fee. To learn more, visit our Customer Service Portal.

Stay near popular Washington Heights attractions

Dr. Percy Julian Residence

Find out about the history of Chicago when you take a trip to Dr. Percy Julian Residence. Make some time to visit the shops while you're in the area.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $64
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.