Illinois Holidays from NZ$2,691

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The Latest Illinois Holiday Deals

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$3,340, price is now NZ$2,691 per person
NZ$2,691
per person
27 Dec - 1 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel

Reviewed on 20 Oct 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was NZ$5,529, price is now NZ$4,214 per person
NZ$4,214
per person
27 Dec - 1 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Great staff, very clean rooms, overall great experience

Reviewed on 31 Oct 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was NZ$3,817, price is now NZ$2,915 per person
NZ$2,915
per person
27 Dec - 1 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
We loved the Pendry!

Reviewed on 27 Oct 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was NZ$3,858, price is now NZ$2,998 per person
NZ$2,998
per person
27 Dec - 1 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
Always a great stay! Staff are great and rooms present great value.

Reviewed on 1 Nov 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was NZ$3,499, price is now NZ$2,807 per person
NZ$2,807
per person
27 Dec - 1 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,852 reviews)
Great staff. Especially front desk and restaurant! Great location.

Reviewed on 3 Nov 2025

Our guide on where to stay in Illinois

Find the best Illinois areas and neighborhoods for the activities you enjoy most. Learn more about Illinois
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 Illinois Hotel Deals

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$242 per night from 23 Nov to 24 Nov
NZ$242
23 Nov - 24 Nov
includes taxes & fees
8.4/10 Very Good! (5,174 reviews)
Completely fell in love with the hotel!

Reviewed on 30 Oct 2025

Embassy Suites by Hilton Chicago Downtown River North
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 NZ$423 per night from 6 Nov to 7 Nov
NZ$423
6 Nov - 7 Nov
includes taxes & fees
7.8/10 Good! (9,665 reviews)
Yes

Reviewed on 3 Nov 2025

Congress Plaza 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 NZ$207 per night from 17 Nov to 18 Nov
NZ$207
17 Nov - 18 Nov
includes taxes & fees
8.8/10 Excellent! (3,220 reviews)
Great staff at the front desk!

Reviewed on 2 Nov 2025

Hilton Chicago/Magnificent Mile Suites
See all 10,245 properties in Illinois
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 Illinois holiday package cost?
We make it simple to travel somewhere new, with Illinois packages starting from as low as NZ$2,691. You'll have the flexibility to bundle your preferred airlines, hotels and car rental. For the ultimate escape, why not add a few tours and experiences to your itinerary?
How do I get a cheap travel package to Illinois?
Booking an Illinois holiday package with Expedia is a great way to save. We have access to more than 550 air carriers and 1 000 000 hotel options all over the world. With such a fabulous range to choose from, you'll have no trouble pulling together your perfect escape.
Where should I stay in Illinois?
Chicago is a wonderful destination to visit. Here, you'll find popular sights including Wrigley Field and Six Flags Great America. Joliet also draws in many travellers eager to check out some of the best attractions in Illinois. These include Rialto Square Theatre and Silver Cross Field.
What are the top hotels in Illinois?
Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton know how to make their guests feel welcome in Chicago. If you also plan to explore Galena, have a look at The Whitehall Hotel and Hyatt Regency Chicago. Both are popular with travellers.
How far in advance should I book my Illinois holiday?
Browse Expedia to compare international airfares as early as possible. In most cases, you can purchase a seat up to 12 months before departure. If you don't see your preferred air carrier, or you've left things to the last moment, don't worry. Cheap fares to Illinois sometimes occur within weeks of departure.
What does an Expedia Illinois travel package include?
Rental cars, flights and hotels — we have them covered. With Expedia, you can create your Illinois travel package however you want. All you have to do is determine what you need. Once you've made your booking, you can add on fun things like tours and activities. The more you bundle, the greater the savings!
What should I know before booking an Illinois travel package?
Locking in all the parts of your holiday together is one of the easiest ways to save. Bundle car rentals, airfares and hotels into one package. But your options don't end at hotels. Expedia features all sorts of properties, including holiday homes like mountain cabins and serviced residences. The list is almost endless!
Can I choose my airline with an Illinois Expedia holiday package?
Yes, definitely. Expedia has more than 550 airline partners to select from globally. With so much choice, finding the ideal carrier to fly you to Illinois won't be difficult.
If I'm not able to travel, can I cancel my Illinois holiday package?
Because we know life can throw you a few curveballs, the answer is yes. For further information, head to our Customer Service Portal. But generally speaking, if you've made your booking in the last 24 hours, you may be able to change or cancel it without penalty. Your airline, hotel or car rental company may charge a fee if your booking is older than that.

Discover the most popular places to visit in Illinois

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

Wrigley Field

4.5/5(21 reviews)

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
Navy Pier

Navy Pier

4.5/5(64 reviews)

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier
McCormick Place

McCormick Place

4.5/5(21 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

What to do in Illinois

River tour boat in Chicago

Architecture River Tour

NZ$85
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

NZ$76
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

NZ$184
per adult
84% of travellers recommend
Chicago C3® by CityPASS®
See all activities in Illinois
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.