Irving Park Holidays from NZ$3,594

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Top Holiday Package Deals in Irving Park

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was NZ$4,995, price is now NZ$3,594 per person
NZ$3,594
per person
2 Apr - 9 Apr
found 17 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Cleanliness, exceptional customer service, and a complimentary upgrade made our stay outstanding! The way the buffet staff efficiently managed the line, guided guests to tables, and consistently kept the food fresh—all while wearing genuine smiles—was truly impressive. Our room was spotless, modern, and well-stocked, exceeding our expectations. We will definitely be back!

Reviewed on 11 Jan 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was NZ$5,057, price is now NZ$3,805 per person
NZ$3,805
per person
2 Apr - 9 Apr
found 17 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Clean room and amenities

Reviewed on 8 Jan 2026

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$4,942, price is now NZ$3,756 per person
NZ$3,756
per person
2 Apr - 9 Apr
found 17 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Great location, clean hotel

Reviewed on 11 Jan 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was NZ$5,065, price is now NZ$3,854 per person
NZ$3,854
per person
2 Apr - 9 Apr
found 17 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in

Reviewed on 25 Dec 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was NZ$7,111, price is now NZ$5,493 per person
NZ$5,493
per person
2 Apr - 9 Apr
found 17 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room.

Reviewed on 11 Jan 2026

Our guide on 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 featuring 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

Our pick of the best Irving Park Hotel Deals

Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$335 per night from 19 Jan to 20 Jan
NZ$335
19 Jan - 20 Jan
includes taxes & fees
8.4/10 Very Good! (2,494 reviews)
I paid for a king room and had that for the first half of my stay, but something went wrong with the water heater for the floor(?). It wasn't explained well to us, but we were moved into another room on a higher level which I assumed would have been similar but it was much smaller and had a queen ...

Reviewed on 5 Jan 2026

Hilton Chicago
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 NZ$183 per night from 18 Jan to 19 Jan
NZ$183
18 Jan - 19 Jan
includes taxes & fees
8.8/10 Excellent! (3,691 reviews)
Yes

Reviewed on 11 Jan 2026

Hilton Chicago/Magnificent Mile Suites
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$167 per night from 25 Jan to 26 Jan
NZ$167
25 Jan - 26 Jan
includes taxes & fees
8.6/10 Excellent! (2,055 reviews)
Super fast and easy check in / out experience, amazing location and very affordable

Reviewed on 11 Jan 2026

Club Quarters Hotel Wacker at Michigan, Chicago
See all 5,019 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 NZ$3,594, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.