Irving Park Holidays

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    Save up to S$134 when you book a flight and hotel together*

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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 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 Irving Park

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 5 Jan to 6 Jan
S$135
5 Jan - 6 Jan, 2026
includes taxes & fees
8.8/10 Excellent! (3,572 reviews)
excellent

Reviewed on 26 Dec, 2025

Hilton Chicago/Magnificent Mile Suites
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$230 per night from 4 Jan to 5 Jan
S$230
4 Jan - 5 Jan, 2026
includes taxes & fees
8.4/10 Very Good! (2,168 reviews)
Decent room and the staff at the front desk and restaurant were friendly and helpful. The front desk area is cramped and confusing (i.e.) once you get your key card from check-in, it is so tight in that area that that it’s unclear how you get out of the area without pushing past the people in line ...

Reviewed on 22 Dec, 2025

Palmer House a Hilton Hotel
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$222 per night from 4 Jan to 5 Jan
S$222
4 Jan - 5 Jan, 2026
includes taxes & fees
8.4/10 Very Good! (2,414 reviews)
Rooms were nice, staff friendly, enjoyed the indoor pool and hot tubs.

Reviewed on 26 Dec, 2025

Hilton Chicago
See all 4,968 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.

Frequently asked questions

How much does an Irving Park holiday package cost?
Perhaps less than you imagined — from a tempting , actually! By bundling hotels, flights and car rentals into a custom-built holiday 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 holiday 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 holiday with the family or going it alone, exploring Irving Park is better with a package.
Where should I stay in Irving Park?
A holiday 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 holiday?
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 travelling 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 holiday package lets you plan your escape your way. Plus, you'll score great discounts when you combine your accommodation 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 holiday package?
We understand — the universe can throw the odd curveball. If you've locked in an Irving Park holiday 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.

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

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$52
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Art Institute of Chicago

Art Institute of Chicago

S$52
per adult
92% of travellers recommend
Art Institute of Chicago
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

S$263
per adult
80% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner 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. 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.