Irving Park East Vacation Packages

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Top Holiday Package Deals in Irving Park East

Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was CA $913, price is now CA $671 per person
CA $671
per person
Jan 21 - Jan 24
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything.

Reviewed on Nov 3, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $1,898, price is now CA $1,336 per person
CA $1,336
per person
Jan 21 - Jan 24
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $1,106, price is now CA $794 per person
CA $794
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)

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $1,801, price is now CA $1,315 per person
CA $1,315
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,344, price is now CA $983 per person
CA $983
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.

Reviewed on Nov 8, 2026

Where to stay in Irving Park East

Find the best Irving Park East areas and neighborhoods for the activities you enjoy most. Learn more about Irving Park East
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

Irving Park East 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 $164 per night from Nov 22 to Nov 23
CA $164
CA $195 total
Nov 22 - Nov 23
includes taxes & fees
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 $164 per night from Nov 15 to Nov 16
CA $164
CA $195 total
Nov 15 - Nov 16
includes taxes & fees
8/10 Very good! (2,695 reviews)
"Love this hotel! It was really nice, staff were very friendly and helpful! Restaurant and bar were perfect and open late. Paid breakfast buffet was nice as well!"

Reviewed on Nov 10, 2026

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 $150 per night from Dec 10 to Dec 11
CA $150
CA $178 total
Dec 10 - Dec 11
includes taxes & fees
River Hotel
See all 4,768 properties in Irving Park East
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 Irving Park East vacation package cost?
The most affordable Irving Park East vacation package is CA $671, so your dream vacation can become a reality — without spending a fortune. Combine flights, hotels, car rentals and more to tailor a package suited to your travel style.
How do I get a cheap travel package to Irving Park East?
Combine your hotels and flights, throw in extras such as activities, and save with an Irving Park East vacation package. You won't just land impressive discounts on your getaway — you'll have plenty of choice too. When you book with Expedia, you can select from more than 550 air carriers and 1,000,000 hotels around the world. Your affordable vacation starts right here, right now!
Where should I stay in Irving Park East?
It makes sense to stay near the action. Many visitors book hotels in the vicinity of popular sights, like Six Corners, Walt Disney House and Kindred Chicago Central Hospital.
How far in advance should I book my Irving Park East vacation?
Reserving your seat early with Expedia means one less thing to have to worry about. Most air carriers display prices up to 12 months prior to departure dates. Usually, this is the cheapest time to book. If circumstances have left you booking late, incredible deals to Irving Park East occasionally appear just weeks before departure.
What does an Expedia Irving Park East travel package include?
Car rentals, hotels and flights — we connect you to all the best deals. All you'll have to do is pick and choose your ideal combination. After you've made your booking, you can add on the fun stuff like day tours and sightseeing activities. Our travel packages make it easy to craft an amazing Irving Park East vacation.
What should I know before booking an Irving Park East travel package?
We already have low prices. However, you'll enjoy even better deals when you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and loads of choice.
Can I choose my airline with an Irving Park East Expedia vacation package?
Expedia has access to more than 550 airline partners globally, so you definitely can. Just pick your preferred carrier and craft your ideal Irving Park East trip.
If I'm not able to travel, can I cancel my Irving Park East vacation package?
Because we understand life can throw you a few curveballs, the answer is yes. For more information, visit our Customer Service Portal. But generally speaking, if you've booked your Irving Park East vacation package in the last 24 hours, you may be able to change or cancel it for no charge. Your airline, hotel or car rental company may charge a fee if you made your booking a while ago.

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.