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
Price found within the past 48 hours. Click for updated prices.
  • Couples treatment rooms, sauna, body treatments, aromatherapy
    Aug 28 - Aug 31

    Wind Creek Southland Casino and Hotel + Flight

    East Hazel Crest
    3 nights
    4.0 star property
    9.4/10 - Exceptional (409 reviews)
    "Clean rooms"
    Reviewed June 4, 2026
    Roundtrip • Toronto (YTZ) - Chicago (MDW)
    YTZ - MDW • Nonstop MDW - YTZ • Nonstop
    CA $1,029
    CA $808
    per traveller
    found 12 hours ago
    Wind Creek Southland Casino and Hotel
  • Premium bedding, pillowtop beds, in-room safe, individually furnished
    Aug 27 - Aug 30

    Level Chicago - River North + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.2/10 - Wonderful (1,012 reviews)
    "I recommend 1000/10, this hotel has everything you need and the location is everything. LOVE LOVE LOVE."
    Reviewed June 3, 2026
    Roundtrip • Toronto (YTZ) - Chicago (MDW)
    YTZ - MDW • Nonstop MDW - YTZ • Nonstop
    CA $1,743
    CA $1,186
    per traveller
    found 6 hours ago
    Level Chicago - River North
  • Lounge
    Jul 8 - Jul 17

    Pendry Chicago + Flight

    Downtown Chicago
    9 nights
    4.5 star property
    9.2/10 - Wonderful (1,121 reviews)
    "I absolutely loved it! I little bit noisy but close to literally everything!"
    Reviewed June 2, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • Nonstop ORD - YUL • Nonstop
    CA $4,036
    CA $2,947
    per traveller
    found 15 hours ago
    Pendry Chicago
  • Meeting facility
    Jul 31 - Aug 3

    Thompson Chicago, by Hyatt + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,377 reviews)
    "The hotel was very clean and a great location within Chicago close to restaurants and shopping."
    Reviewed June 2, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $2,024
    CA $1,581
    per traveller
    found 1 day ago
    Thompson Chicago, by Hyatt
  • Terrace/patio
    Aug 21 - Aug 24

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,881 reviews)
    "⭐⭐⭐⭐⭐ Amazing stay! Beautiful hotel, incredible views, excellent service, and a perfect location in downtown Chicago. Everything exceeded our expectations. We loved every minute of our stay and would definitely return. Highly recommended!"
    Reviewed June 4, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • Nonstop ORD - YUL • Nonstop
    CA $2,066
    CA $1,635
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago

Where to stay in Irving Park

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

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 $194 per night from Jun 29 to Jun 30
CA $194
CA $230 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,171 reviews)
"Good spot. Nice staff. Great location."

Reviewed on Jun 5, 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 $211 per night from Jun 28 to Jun 29
CA $211
CA $251 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,518 reviews)
"Clean room"

Reviewed on Jun 3, 2026

The Chicago Hotel Collection - Magnificent Mile
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $263 per night from Jun 30 to Jul 1
CA $263
CA $352 total
Jun 30 - Jul 1
includes taxes & fees
9.4/10 Exceptional! (4,341 reviews)
"Great location and roof top bar!! The hotel is new and the decoration is beautiful!! Room was good and clean. The only thing I didn’t like was the bed … it was too soft. I hope they sdd boiled eggs as an option for breakfast"

Reviewed on Jun 5, 2026

Hotel Riu Plaza Chicago
See all 4,884 properties in 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
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Frequently asked questions

How much does an Irving Park vacation package cost?
Perhaps less than you imagined — from a tempting , actually! By bundling hotels, flights and car rentals into a custom-built vacation package, your getaway to Irving Park is just a few clicks away.
How do I get a cheap travel package to Irving Park?
Think of all the fabulous things you could do in Irving Park with a wad of extra cash in your wallet. Watch your savings stack up when you combine your hotel and airfare bookings into an Irving Park vacation package. You have loads of choice when you book your trip with Expedia too. In fact, you can select from more than 550 air carriers and 1,000,000 properties throughout the world. Whether you're taking a vacation with the family or going it alone, exploring Irving Park is better with a package.
Where should I stay in Irving Park?
A vacation in Irving Park isn't complete without checking out Portage Park, Six Corners and Walt Disney House. Spend your evenings near these popular sights and make sightseeing simple.
How far in advance should I book my Irving Park vacation?
It can be tricky to know exactly when is the ideal time to book your Irving Park trip. But generally the earlier you book, the better the prices. Sometimes, you can secure your flights and hotels nearly a year before your departure date. If you're considering a last-minute getaway, no need to panic! There are plenty of fantastic bargains posted on Expedia every day.
What does an Expedia Irving Park travel package include?
Rental cars, hotels and flights, or any combination of them — the choice is yours. Whether you're exploring Irving Park on a family road trip or traveling solo, there's a package to fit every budget and style. Once you've made your booking, why not add on one or two activities?
What should I know before booking an Irving Park travel package?
Whether it's relaxation or adventure you're craving, an Irving Park vacation package lets you plan your escape your way. Plus, you'll score great discounts when you combine your accommodations with your rental car and flights. The more you bundle, the more you'll save!
If I'm not able to travel, can I cancel my Irving Park vacation package?
We understand — the universe can throw the odd curveball. If you've locked in an Irving Park vacation package and need to cancel or amend it, we're here to help. We recommend browsing our Customer Service Portal first for information. But generally, if you've taken out your package in the last 24 hours, you may be able to cancel and rebook for free. If it's been longer than 24 hours, your hotel, airline or car rental company may impose a charge.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
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 $68
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.