Old Irving Park Holidays

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Price found within the past 48 hours. Click for updated prices.
Grand Royal Hotel O'Hare - Chicago

Grand Royal Hotel O'Hare - Chicago

3.5 out of 5
Price was S$907, price is now S$691 per person
S$691
per person
28 Mar - 4 Apr
found 24 hours ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
5.8/10 (215 reviews)
Friendly front desk, easy and convenient for my overnight layover in Chicago

Reviewed on 7 Nov, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Save 100% on your flight
Price was S$2,021, price is now S$1,404 per person
S$1,404
per person
28 Mar - 4 Apr
found 24 hours ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Great stay fir early flights

Reviewed on 8 Jan, 2026

Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 out of 5
Price was S$1,516, price is now S$1,165 per person
S$1,165
per person
28 Mar - 4 Apr
found 24 hours ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
The room and staff were extremely friendly, but I specifically requested a room with a bath so I could soak my leg after a surgery. There was absolutely no water pressure when it came to the bath and the drain wouldn't close all the way. For how much I paid I feel like I should have been able to take a bath

Reviewed on 8 Dec, 2025

DoubleTree by Hilton Chicago - Oak Brook

DoubleTree by Hilton Chicago - Oak Brook

4 out of 5
Price was S$1,245, price is now S$957 per person
S$957
per person
28 Mar - 4 Apr
found 24 hours ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
6.8/10 (1,000 reviews)
Hotel is old and showing its age. Rooms are old too. Few amenities etc.

Reviewed on 6 Jan, 2026

Motel Edgebrook Chicago North Shore by OYO

Motel Edgebrook Chicago North Shore by OYO

2 out of 5
Forest Glen
Price was S$984, price is now S$757 per person
S$757
per person
28 Mar - 4 Apr
found 24 hours ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
6.2/10 (365 reviews)
dated, lamp shade missing, overall dumpy place

Reviewed on 19 Dec, 2025

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 which includes a city

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

Top hotels in Old Irving Park

Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$247 per night from 16 Jan to 17 Jan
S$247
16 Jan - 17 Jan
includes taxes & fees
8.4/10 Very Good! (2,501 reviews)
Everything was amazing abt my stay

Reviewed on 7 Jan, 2026

Hilton Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$248 per night from 17 Jan to 18 Jan
S$248
17 Jan - 18 Jan
includes taxes & fees
8.4/10 Very Good! (2,225 reviews)
This stay was perfection from beginning to end. Totally wonderful experience in every way.

Reviewed on 9 Jan, 2026

Palmer House a Hilton Hotel
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 S$135 per night from 18 Jan to 19 Jan
S$135
18 Jan - 19 Jan
includes taxes & fees
8.8/10 Excellent! (3,678 reviews)
Room and hotel overall very clean. Noted some things that could be updated in bathroom(stopper in sink didnt go all the way down, peeling caulk and some missing grout). Minor updates. Our sink was clogged when we checked in and I called the front desk, housekeeping and the hotel hotline 4 different ...

Reviewed on 7 Jan, 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,989 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.

Frequently asked questions

How much does an Old Irving Park holiday package cost?
Discover the best of Old Irving Park from just S$691. 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 holiday 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 holiday?
Travellers 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 holiday 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 holiday package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines throughout the world. Our holiday 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 holiday 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.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Soldier Field showing a city, modern architecture and a skyscraper

Soldier Field

4/5(44 reviews)

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field

Things to do

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

S$57
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$32
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

S$51
per adult
92% of travellers recommend
Art Institute of Chicago
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.