Chicago Holidays from NZ$1,971

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The Latest Chicago Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Ohio House Motel

Ohio House Motel

2.5 out of 5
Downtown Chicago
per person
24 Jan - 26 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
My best friends and I was in a good location everything was great

Reviewed on 22 Nov. 2024

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
24 Jan - 26 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
8/10 Very Good! (1,129 reviews)
I loved how conveniently located it was, the staff was friendly, room was clean and I felt very safe! Would definitely return!

Reviewed on 20 Nov. 2024

citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Downtown Chicago
per person
24 Jan - 26 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (2,053 reviews)
My husband and I stayed for just one night. The room was super tiny! Much smaller than we expected. Even though it was tiny, it was very clean and super high tech. Your iPad controls everything in the room, the lights, curtains, temp, and tv. The lights can be changed to almost any color. I loved how the king bed was nestled up to the window. So we could see Michigan Avenue while sitting in bed. I would definitely come back here! Only complaint is self parking is a pain and some of the employees weren’t the friendliest.

Reviewed on 22 Nov. 2024

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
per person
24 Jan - 26 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
7.8/10 Good! (7,993 reviews)
The room was beautiful with high ceilings and a great view of the parks across the street.

Reviewed on 23 Nov. 2024

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
Downtown Chicago
per person
24 Jan - 26 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
8.2/10 Very Good! (1,429 reviews)
Great place great staff

Reviewed on 22 Nov. 2024

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

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

5 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 hotel + flight trips in Downtown Chicago

Chicago Holiday

Our pick of the best Chicago 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$259 per night from 4 Dec to 5 Dec
NZ$259
includes taxes & fees
4 Dec - 5 Dec
7.8/10 Good! (8,150 reviews)
"Perfect Place To Stay! Walkable To Everything!"

Reviewed on 22 Nov. 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$200 per night from 24 Dec to 25 Dec
NZ$200
includes taxes & fees
24 Dec - 25 Dec
8.6/10 Excellent! (3,544 reviews)
Book with confidence!
"Booked: two bedroom suite Condition: bed was very comfy and linens felt lovely. Bathroom was well appointed. Spotlessly clean. Rooms could use a remodel and a spruce up, BUT it was not offensively outdated and I have NO complaints on the quality of the space. Microwave also functions as a convection ..."

Reviewed on 20 Nov. 2024

River Hotel
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
The price is NZ$333 per night from 16 Dec to 17 Dec
NZ$333
includes taxes & fees
16 Dec - 17 Dec
8.6/10 Excellent! (1,005 reviews)
"This is in a fancy part of town, across from the Hancock bldg. There are tons of great restaurants. The shops are… also fancy, translated - mostly for window shopping. It would be awesome if they had 2 people serving coffee in the morning because the line is long."

Reviewed on 21 Nov. 2024

The Westin Michigan Avenue Chicago
See all 4,864 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?
Starting from as low as NZ$1,971, you can handcraft your own Chicago package the way you want. Simply bundle hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Chicago?
Find flights that fit in with your schedule, add a hotel to your booking and watch how much you save with a Chicago holiday package. It’s as easy as that! From flights and hotels to activities and rental cars, Expedia is where your cheap getaway begins. And with more than 550 partner airlines and 1 000 000 properties across the globe to pick from, you won’t be short of choice.
Where should I stay in Chicago?
Central Chicago is an excellent place to stay in Chicago. With interesting attractions like Millennium Park and Willis Tower within easy reach, you won’t have to worry about running out of things to do here. Magnificent Mile is another option. This place has plenty to offer travellers, including John Hancock Centre and Chicago Water Tower.
What are the top hotels in Chicago?
Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton are some favourite options in the neighbourhood of Central Chicago. If you’d rather stay in the North Side area, consider locking in a room at The Whitehall Hotel or Hyatt Regency Chicago.
How far in advance should I book my Chicago holiday?
While not all air carriers release ticket prices early, you can normally start comparing international flights on Expedia up to 12 months in advance. This is the time you can bag some fantastic deals. If you’re booking last minute, you may still be in luck. Discounted prices occasionally appear a few weeks prior to departure.
What does an Expedia Chicago travel package include?
Hotels, flights and rental cars — we have them well covered. With Expedia, you can shape your Chicago package just how you like it. All you have to do is work out exactly 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 your savings!
What should I know before booking a Chicago travel package?
We already have low prices. However, you’ll pick up even more bargains when you book your flights, hotels and car rentals together. With an Expedia travel package, you’ll always get transparent pricing and a huge range of choice.
Can I choose my airline with a Chicago Expedia holiday package?
Yes, of course. We have more than 550 partner airlines globally, so fly with the carrier that fits your budget and travel needs.
If I'm not able to travel, can I cancel my Chicago holiday package?
We totally get that life sometimes gets in the way of your plans. If you’ve booked a Chicago holiday package and have to amend or cancel it, we’re here to help. We suggest visiting our Customer Service Portal first for information. But generally speaking, if you’ve booked your package in the last 24 hours, you may be able to cancel or change your itinerary at no cost. If it’s been longer than 24 hours, your airline, hotel or car rental company may charge a fee.

Discover the most popular places to visit in Chicago

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
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

What to do in Chicago

Flyover in Chicago

Flyover in Chicago

NZ$63
Per adult
94% of travellers recommend
Flyover in Chicago
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

NZ$74
Per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
River tour boat in Chicago

Architecture River Tour

NZ$89
Per adult
94% of travellers recommend
Architecture River Tour
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.