Old Irving Park 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 Old Irving Park

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,296, price is now CA $921 per person
CA $921
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
We stayed at this hotel for a small wedding venue. I booked the larger room and was glad I did. The hotel was close for walking to restaurants and some bars. The front desk was very friendly and helpful.

Reviewed on Jun 19, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,999, price is now CA $1,337 per person
CA $1,337
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.

Reviewed on Jun 11, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,887, price is now CA $1,262 per person
CA $1,262
per person
Aug 27 - Aug 31
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,019 reviews)
I loved how simple and easy it was to access everything.

Reviewed on Jun 16, 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 $2,315, price is now CA $1,667 per person
CA $1,667
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
Great location and food court in area. Great for family fun

Reviewed on Jun 17, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,541, price is now CA $1,138 per person
CA $1,138
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,127 reviews)
We were celebrating an anniversary. We had a greay stay. It was close to all the shopping and restaurants, staff were great and helpful. We will be back again!

Reviewed on Jun 18, 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
Downtown Chicago

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

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 $193 per night from Jun 29 to Jun 30
CA $193
CA $229 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,130 reviews)
"The facilities are very old, and there is a musty smell in the room."

Reviewed on Jun 18, 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is CA $193 per night from Jun 28 to Jun 29
CA $193
CA $229 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,595 reviews)
"seems like we are visiting every other month to meet up with friends. We have already recommended this hotel many times and will definitely be staying again."

Reviewed on Jun 19, 2026

The Chicago Hotel Collection - Magnificent Mile
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $221 per night from Jul 5 to Jul 6
CA $221
CA $263 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (4,443 reviews)
"Perfect for weekend stay"

Reviewed on Jun 19, 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,852 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
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does an Old Irving Park vacation package cost?
Discover the best of Old Irving Park from just CA $921. 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.

Discover the most popular places to visit in Old Irving Park

Wrigley Field

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
A coastal cityscape with high-rise buildings, a marina, and a park area.

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

CA $69
per adult
94% of travellers recommend
Chicago By Night River and Lake Cruise
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.