Chicago Holidays from NZ$3,096

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The Latest Chicago Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
21 Jun - 26 Jun
found 2 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,320 reviews)
Spent a long weekend here and it was great. Staff was friendly and location of hotel was perfect for sightseeing and walking to most things downtown. Our room was clean and quiet. Loved the large bathroom and closest area. Highly recommend!

Reviewed on 13 Apr. 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
21 Jun - 26 Jun
found 2 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (295 reviews)
Only thing was no communication on the pool location and the arcade games so I just didn't go and how to work the stove other that it was a beautiful experience. I think you should let people smoke on the balcony. I mean it is a expensive location and marijuana is legal a recreational use think about it.

Reviewed on 13 Apr. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
21 Jun - 26 Jun
found 2 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,546 reviews)
Rooms were clean and spacious. Disappointed at the bar staff, not very engaging.

Reviewed on 6 Apr. 2025

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
per person
21 Jun - 26 Jun
found 2 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
The staff was 10/10 and the rooms were clean and tidy. 10/10

Reviewed on 15 Apr. 2025

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
per person
21 Jun - 26 Jun
found 2 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,013 reviews)
the hotel is very well run and the staff is super friendly and helpful. the breakfast could be better in terms of food. location is good

Reviewed on 14 Apr. 2025

Our guide on where to stay in Chicago

Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago
Downtown Chicago featuring a city

Downtown Chicago

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Chicago Holiday

Our pick of the best Chicago 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
The price is NZ$299 per night from 20 Apr to 21 Apr
NZ$299
includes taxes & fees
20 Apr - 21 Apr
8.2/10 Very Good! (3,893 reviews)
Loved it. Great for family’s.
"Amazing hotel, great service! Breakfast was good with lots of options! Complementary snacks and drinks in the afternoon! Haven’t had a hotel before offer so many complementary items especially in Chicago! The breakfast and snacks saved us so much money! Will stay here again for sure!"

Reviewed on 14 Apr. 2025

Embassy Suites by Hilton Chicago Downtown River North
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
The price is NZ$410 per night from 18 Apr to 19 Apr
NZ$410
includes taxes & fees
18 Apr - 19 Apr
8.8/10 Excellent! (2,043 reviews)
"The hotel is nice. The amenities are good."

Reviewed on 12 Apr. 2025

Swissotel - Chicago
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is NZ$184 per night from 20 Apr to 21 Apr
NZ$184
includes taxes & fees
20 Apr - 21 Apr
8.6/10 Excellent! (1,018 reviews)
Great place
"Upon arriving I had a few obstacles getting a early check in. However the manager Alan intervened and took care of everything. My room had a great view, it was clean and very well lit."

Reviewed on 12 Apr. 2025

Crowne Plaza Chicago West Loop by IHG
See all 4,929 properties in Chicago
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 a Chicago holiday package cost?
You’ll find cheap prices from NZ$3,096 on Expedia for your Chicago escape. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your holiday to Chicago costs.
What are the cheapest months to go to Chicago?
December, January and February are the best times to look for cheap Chicago holiday packages. Opting to travel in quieter periods means you’ll typically find lower prices on accommodation and flights.
How many days is enough for Chicago?
To fully enjoy a Chicago holiday, we recommend booking for 2 days. Divide your time between visiting Michigan Avenue, Chicago Riverwalk and other well-known attractions, on top of experiencing neighbourhoods like Central Chicago and Near North Side. If you’ve got some spare time, include a day trip or tour in your Chicago holiday itinerary.
Is it worth booking a holiday package to Chicago?
Chicago has everything you need for a fantastic trip — views, dining and culture are just the start. Whether you want to visit attractions like Navy Pier and Soldier Field, or take the road less traveled, you’ll find plenty to do on your Chicago holiday.
How to find the best Chicago package deals?
Use Expedia’s filters to find some great Chicago package deals. When you start your search, just set your maximum budget and then order the results by “Price: low to high.” If you want to save, plan your trip for midweek, or browse for Chicago package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it’s typically best to lock in your holiday package well in advance.
Is it cheaper to book a Chicago holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You’ll usually score a better deal than booking each component separately. And you’ll still have the freedom to create a customised Chicago holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Chicago?
Secure incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Chicago break.
How to plan a trip to Chicago?

  1. Choose when to travel: Check your diary and get your bags packed. Your preferred season and the activities available will also help you decide when to escape to Chicago.
  2. Set a budget: Factor in costs like flights, transportation and food when working out how much to put aside for your trip to Chicago. Then, choose a property that suits your budget, whether that’s an affordable stay or a swankier getaway.
  3. Work out your trip length: Consider how long you’d like to spend discovering Chicago. Plan your days so you can get to all the attractions and activities you’re interested in without rushing.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that’s left is to choose a Chicago holiday package that brings all your bookings together.

Discover the most popular places to visit in Chicago

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
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
Six Flags Great America featuring rides

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

What to do in Chicago

Flyover in Chicago

Flyover in Chicago

NZ$67
per adult
98% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

NZ$85
per adult
94% of travellers recommend
Architecture River Tour
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

NZ$78
per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
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.