York Center Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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 York Center

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $2,559, price is now CA $1,037 per person
CA $1,037
per person
Dec 19 - Dec 23
found 4 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Save 100% on your flight
Price was CA $2,031, price is now CA $1,315 per person
CA $1,315
per person
Dec 24 - Dec 31
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,005 reviews)
Nice parking garage to park in. When booked, stated wifi free on two devices. We only used two devices and was charge $89 for use of wifi. That false advertising. Staff was friendly. Cleanliness is not top priority and maintenance is lacking.

Reviewed on Nov 1, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,908, price is now CA $1,314 per person
CA $1,314
per person
Jan 24 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (1,358 reviews)

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $2,339, price is now CA $1,641 per person
CA $1,641
per person
Jan 17 - Jan 21
found 19 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,233, price is now CA $1,616 per person
CA $1,616
per person
Jan 24 - Jan 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)

Where to stay in York Center

Find the best York Center areas and neighborhoods for the activities you enjoy most. Learn more about York Center
A busy city street with tall buildings, a bus, and cars.

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.

Find hotels in Downtown Chicago

York Center Hotel Deals

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 $162 per night from Nov 10 to Nov 11
CA $162
CA $193 total
Nov 10 - Nov 11
includes taxes & fees
8/10 Very good! (10,080 reviews)
"I stayed on Halloween and the room next to me was so incredibly loud and I know it was Halloween but it was ridiculous. Their party lasted until 1:00 in the morning and it sounded like it was in my room ."

Reviewed on Nov 1, 2026

Congress Plaza Hotel
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 $38 per night from Nov 22 to Nov 23
CA $38
CA $242 total
Nov 22 - Nov 23
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $166 per night from Nov 23 to Nov 24
CA $166
CA $198 total
Nov 23 - Nov 24
includes taxes & fees
River Hotel
See all 4,906 properties in York Center
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
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a York Center vacation package cost?
From just CA $1,037. Yes, you read that correctly. Our York Center vacation packages are an awesome way to stretch your budget. Bundle your preferred flights, hotels and rental car and get out and see this destination your way.
How do I get a cheap travel package to York Center?
One word: bundle. Hotels, rental cars and flights — combine whatever you need into a York Center vacation package and save. Score even bigger bargains when you include extras such as tours or experiences to your booking. But that's not the only impressive part. You have the freedom to put together your vacation your own way. We offer more than 550 airlines and 1,000,000 properties across the world, so that everyone has an opportunity to travel and fulfill those vacation dreams.
Where should I stay in York Center?
York Center is home to several fascinating places to discover, including Drury Lane Theater. Spend your nights in a hotel close by and make sightseeing hassle-free.
How far in advance should I book my York Center vacation?
It depends on the air carrier, but you can usually browse through international fares on Expedia up to a year in advance. While it's advisable to book ahead of time, lucky customers will occasionally score a cheaper seat just weeks prior to their intended journey.
What does an Expedia York Center travel package include?
Expedia has everything you need to organize your York Center getaway, but what your package looks like is totally up to you. Pick from any combination of flights, hotels and rental cars. Chasing some tours or activities to keep you on the go? Once you've made your booking, you can add them on too. Whatever your style or budget, there's a package to suit your needs.
What should I know before booking a York Center travel package?
A travel package can be more affordable than individually booking all you need for your getaway. For example, bundle your hotels, flights and rental cars and save big. Whatever kind of vacation you're planning, you're bound to find a package within your budget.
Can I choose my airline with a York Center Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines around the world. Our vacation packages give you the freedom to pick from available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my York Center vacation package?
It is possible to cancel your York Center booking if your plans have been upended. Whether you'll incur a penalty or not depends on your airline, hotel or car rental company. You may be able to change or cancel your booking for free if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $60
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
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.