Irving Park Vacation Packages
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Top Holiday Package Deals in Irving Park
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,271
per person
Nov 13 - Nov 16
found 2 days ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
My Labor Day weekend stay at Trump International Hotel & Tower Chicago was exceptional in every regard, marked by refined service, remarkable amenities, and a level of hospitality that felt both genuine and elevated. From the moment I arrived, the staff set a distinguished tone, greeting me with champagne and ensuring every detail of my visit was handled with care. The concierge team was attentive and polished, and throughout my stay I felt consistently supported by a standard of service that exceeded expectations.
Room 2791 offered a breathtaking view of the city, with floor‑to‑ceiling windows framing Chicago’s skyline in a way that felt both serene and spectacular. The terrace added an unforgettable dimension, providing a private space to enjoy the city’s energy from above while still feeling completely at ease. Room service was prompt, beautifully prepared, and consistently excellent, enhancing the comfort of the stay.
The spa and wellness facilities were equally impressive. Ashanti, Christian, and Byron delivered warm, professional service that made each visit feel personal, and my massage therapist provided a treatment that was both restorative and skillfully executed. The sauna, steam room, and gym were immaculate, calming, and thoughtfully maintained, offering a perfect balance of relaxation and rejuvenation. Pablo also stood out for his gracious and attentive service.
This stay left a lasting impression, and I will be making Trump Hotels a part of future travels.✨
Reviewed on Sep 18, 2026
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
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.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Irving Park Hotel Deals
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
CA $255
CA $303 total
Sep 27 - Sep 28
includes taxes & fees
8.8/10 Excellent! (5,447 reviews)
"Well located and affordable hotel, but lots of dust in surprising places."
Reviewed on Sep 19, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $250
CA $297 total
Oct 7 - Oct 8
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $224
CA $267 total
Sep 29 - Sep 30
includes taxes & fees
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.
Frequently asked questions
How much does an Irving Park vacation package cost?
Perhaps less than you imagined — from a tempting CA $784, 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.
Stay near popular Irving Park attractions
Irish American Heritage Center
You can spend an afternoon browsing the exhibits at Irish American Heritage Center in Chicago. Take in the live music while you're in the area.
Avondale Music Hall
You can enjoy a show at Avondale Music Hall on your trip to Chicago. Take in the live music while you're in the area.
Live Wire Lounge
After visiting Live Wire Lounge, make a plan to see the other sights and activities in Chicago. Take in the live music while you're in the area.
Montrose Saloon
Montrose Saloon is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Take in the live music while you're in the area.
COLOR CLUB
COLOR CLUB is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Take in the live music while you're in the area.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.