Old Irving Park Vacation Packages

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Top Holiday Package Deals in Old Irving Park

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 $1,110, price is now CA $797 per person
CA $797
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)
First time ever in Chicago and it was fabulous. The hotel was beautiful. Staff was friendly. We paid for the view and it was phenomenal. Definitely recommend.

Reviewed on Nov 12, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,079, price is now CA $1,318 per person
CA $1,318
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,572 reviews)
Great location. Rooms are spacious and staff is amazing!! I would highly recommend!!!

Reviewed on Nov 12, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,806, price is now CA $1,260 per person
CA $1,260
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $1,944, price is now CA $1,379 per person
CA $1,379
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $3,256, price is now CA $2,339 per person
CA $2,339
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
This place was amazing and the hotel staff was extremely helpful

Reviewed on Nov 10, 2026

Where to stay in Old Irving Park

Find the best Old Irving Park areas and neighborhoods for the activities you enjoy most. Learn more about Old Irving Park
A cityscape with tall skyscrapers and a historic tower.

Downtown Chicago

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Old Irving Park 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 $165 per night from Nov 22 to Nov 23
CA $165
CA $197 total
Nov 22 - Nov 23
includes taxes & fees
8/10 Very good! (10,068 reviews)
"Clean room and nice lobby but the restaurants were all closed and it was impossible to sleep in with the loud construction noise in the hotel"

Reviewed on Nov 12, 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 $165 per night from Nov 15 to Nov 16
CA $165
CA $196 total
Nov 15 - Nov 16
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 $151 per night from Dec 10 to Dec 11
CA $151
CA $180 total
Dec 10 - Dec 11
includes taxes & fees
8.8/10 Excellent! (5,599 reviews)
"Great location and lovely staff"

Reviewed on Nov 12, 2026

River Hotel
See all 4,695 properties in Old Irving Park
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
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Frequently asked questions

How much does an Old Irving Park vacation package cost?
Discover the best of Old Irving Park from just CA $797. Choose from a great selection of flights, rental cars and hotels to suit your travel style. You can pick up even better deals when you add a couple of sightseeing tours to your vacation package.
How do I get a cheap travel package to Old Irving Park?
One of the easiest ways to save money (and time) is to bundle your bookings with Expedia. Flights, rental cars, hotels and activities — we've got them all. Pick and choose a combination that suits your style and see your savings pile up. Of course, a travel package is never a one-size-fits-all. That's why we offer more than 550 partner airlines and 1,000,000 properties across the world, which lets you customize your Old Irving Park adventure.
Where should I stay in Old Irving Park?
A getaway to Old Irving Park isn't complete without visiting Portage Park, Six Corners and Walt Disney House. Stay near these top sights and make sightseeing simple.
How far in advance should I book my Old Irving Park vacation?
Travelers can normally look up international airfares on Expedia up to 12 months prior to departure. Booking late? With a bit of luck, it's still possible to score a cheap ticket just weeks before your journey.
What does an Expedia Old Irving Park travel package include?
Much of that is up to you. You can pick from a range of Old Irving Park packages, such as a hotel, flight and rental car. You can also book a hotel with a flight, or a flight and a rental car. Once you've made your booking, you can add on the fun stuff like experiences and tours. Whatever your Old Irving Park vacation looks like, get set to save!
What should I know before booking an Old Irving Park travel package?
So many places to explore, so many things to see. With a package, you can cross more of them off your list. Combine your hotels, flights and rental cars and get ready to save.
Can I choose my airline with an Old Irving Park Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines throughout the world. Our vacation packages give you the flexibility to pick from available flights, hotels and activities that fit your needs.
If I'm not able to travel, can I cancel my Old Irving Park vacation package?
You can cancel your Old Irving Park booking if your plans have changed. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. You may be able to cancel or change your booking for free if you booked in the last 24 hours. Visit our Customer Service Portal for more information.

Stay near popular Old Irving Park attractions

Six Corners

You can browse for the perfect souvenirs at Six Corners during your stay in Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.
See properties

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 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $57
per adult
94% of travellers recommend
Wendella's 90-min Chicago 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.