Illinois Holidays from NZ$4,270

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Top destinations in Illinois

Chicago which includes a high-rise building and a city as well as a family
FlightsFlightsHotelsHotels

Chicago

Chicago

The Latest Illinois Holiday Deals

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$6,206, price is now NZ$4,270 per person
NZ$4,270
per person
30 May - 4 June
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
It was a wonderful visit with not one complaint about the amenities, cleanliness or staff!

Reviewed on 19 Mar 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was NZ$5,697, price is now NZ$4,568 per person
NZ$4,568
per person
30 May - 4 June
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
The staff was super helpful and very welcoming. The room had an amazing view for us, beings it was our first time being in Chicago. It’s was so close to everything we wanted to visit and super convenient. I will most definitely stay at this hotel again for future stays in the city.!! Thank you so much for taking pride in your establishment, and your employees, as both we’re definitely deserving of a 5 star rating and review.!

Reviewed on 17 Mar 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

4.5 out of 5
Downtown Chicago
Price was NZ$5,628, price is now NZ$4,551 per person
NZ$4,551
per person
30 May - 4 June
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,414 reviews)
Check in was quick and easy, room was clean and spacious

Reviewed on 9 Mar 2026

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Price was NZ$5,406, price is now NZ$4,541 per person
NZ$4,541
per person
30 May - 4 June
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,021 reviews)
I would have rated all 5 star but the restaurant Atwood was closed and we weren’t notified in time to change plans! The staff and (Mr.Brown ) were extremely accommodating! It was my bday and they decorated our room with all sorts of goodies including a hand made stuffed wash cloth doggie! Our housekeeper was amazing too! The room decor is such fun and extremely clean! The only drawback is the rooms are very small and some not configured well! All and all it’s a wonderful place to experience!!!!🍍

Reviewed on 18 Mar 2026

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Price was NZ$5,177, price is now NZ$4,393 per person
NZ$4,393
per person
30 May - 4 June
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.8/10 Excellent! (1,894 reviews)
I’ve asked for a room with bathtub but they gave me room with shower instead. It’s my way of taking bathe and relaxing in the bathtub but I was disappointed.

Reviewed on 18 Mar 2026

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

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$252 per night from 20 Mar to 21 Mar
NZ$252
20 Mar - 21 Mar
includes taxes & fees
8/10 Very Good! (9,975 reviews)
I spent 2 nights and everything was great. I'll be back!

Reviewed on 18 Mar 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$313 per night from 24 Mar to 25 Mar
NZ$313
24 Mar - 25 Mar
includes taxes & fees
9.4/10 Exceptional! (3,565 reviews)
It was a wonderful visit with not one complaint about the amenities, cleanliness or staff!

Reviewed on 19 Mar 2026

Hotel Riu Plaza Chicago
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$264 per night from 29 Mar to 30 Mar
NZ$264
29 Mar - 30 Mar
includes taxes & fees
8.6/10 Excellent! (5,743 reviews)
Good room lower floor was a little close to the street and a little loud but it’s Chicago so to be expected. Breakfast was good and the room was clean.

Reviewed on 18 Mar 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 10,451 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$4,270. 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.