Greater Grand Crossing Holidays from NZ$2,216

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Top Holiday Package Deals in Greater Grand Crossing

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$2,620, price is now NZ$2,216 per person
NZ$2,216
per person
22 Dec - 27 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
My room was very clean. The stay was very friendly and helpful. Check-in was a breeze. Since my room was ready they even let me check in early! There are 2 restaurants in this hotel. We had drinks at the one near the lobby and we ate at the ROOF. The food was delish! The environment was fun. We were worried that it was going to be more for the 20 something crowd, but there were adults of every age there. This hotel is also just steps from The Chicago Theatre which makes it super convenient when seeing an event there.

Reviewed on 10 Nov 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was NZ$4,972, price is now NZ$3,955 per person
NZ$3,955
per person
22 Dec - 27 Dec
found 3 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.8/10 Exceptional! (1,009 reviews)
Staff is always there for your every need. Excellent clean room. Quiet and luxurious

Reviewed on 7 Nov 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was NZ$2,690, price is now NZ$2,263 per person
NZ$2,263
per person
22 Dec - 27 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,852 reviews)
Great location, friendly staff, lovely rooms!

Reviewed on 10 Nov 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was NZ$3,882, price is now NZ$3,296 per person
NZ$3,296
per person
21 Dec - 26 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
8.2/10 Very Good! (2,141 reviews)
It's an old airport hotel. What does one should expect, 5 stars?? Served the purpose. Didn't eat food only slept for one night due to the flight cancelation.

Reviewed on 10 Nov 2025

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Downtown Chicago
Price was NZ$2,774, price is now NZ$2,360 per person
NZ$2,360
per person
22 Dec - 27 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (3,013 reviews)
Clean room, super nice, walkable distance to everything

Reviewed on 10 Nov 2025

Our guide on where to stay in Greater Grand Crossing

Find the best Greater Grand Crossing areas and neighborhoods for the activities you enjoy most. Learn more about Greater Grand Crossing
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 Greater Grand Crossing 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$212 per night from 8 Dec to 9 Dec
NZ$212
8 Dec - 9 Dec
includes taxes & fees
8.4/10 Very Good! (5,199 reviews)
It was fine

Reviewed on 5 Nov 2025

Embassy Suites by Hilton Chicago Downtown River North
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$211 per night from 7 Dec to 8 Dec
NZ$211
7 Dec - 8 Dec
includes taxes & fees
8.8/10 Excellent! (3,243 reviews)
Large, clean spacious rooms. Convenient to shopping and restaurants. A very good bargain for the price.

Reviewed on 8 Nov 2025

Hilton Chicago/Magnificent Mile Suites
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
8/10 Very Good! (9,538 reviews)
a

Reviewed on 8 Nov 2025

Get rates
Congress Plaza Hotel
See all 4,563 properties in Greater Grand Crossing
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 Greater Grand Crossing holiday package cost?
Live it up in Greater Grand Crossing from just NZ$2,216. Choose from a wonderful selection of hotels, flights and rental cars to suit every budget and style. Pick up even better deals when you add some activities or tours to your package.
How do I get a cheap travel package to Greater Grand Crossing?
Just imagine all the fabulous things you could do in Greater Grand Crossing with extra cash in your wallet. Watch your savings stack up when you bundle your travel bookings into a Greater Grand Crossing holiday package. You have plenty of choice when you book with Expedia too. In fact, you can select from over 550 airlines and 1 000 000 properties around the world. Whether you're taking off with the entire family or going it alone, organising a getaway to Greater Grand Crossing is better with a package.
Where should I stay in Greater Grand Crossing?
A visit to Greater Grand Crossing isn't complete without seeing University of Chicago and Chicago Museum of Science and Industry. Reserve a room close by for quick access to these famous sights.
How far in advance should I book my Greater Grand Crossing holiday?
While not all airlines advertise ticket prices early, customers are usually able to look up international flights on Expedia up to 12 months in advance. This is the time when you can nab some incredible bargains. If you're purchasing tickets last minute, you might still be in luck. Low prices occasionally become available just weeks prior to departure.
What does an Expedia Greater Grand Crossing travel package include?
That depends on you. You can select from a variety of Greater Grand Crossing packages, such as a hotel, rental car and flight. You can also book a hotel with a flight, or a rental car with a flight. Once you've made your booking, you can add the fun stuff like tours and activities. Whatever your ideal Greater Grand Crossing break looks like, get set to save!
What should I know before booking a Greater Grand Crossing travel package?
You'll pick up great savings when you bundle your hotels, flights and rental cars into a package. Not only that, booking everything in one place just makes things easier. So why waste your time or money? Whether you're organising a luxury city stay with your love or a budget solo adventure, take a look at our holiday packages today.
Can I choose my airline with a Greater Grand Crossing Expedia holiday package?
Yes, and with more than 550 airlines to choose from worldwide, you have loads of choice. Take a look at the available options and see which airline best suits your needs and budget.
If I'm not able to travel, can I cancel my Greater Grand Crossing holiday package?
Plans can change unexpectedly, so yes, you can. You may be able to cancel and rebook your Greater Grand Crossing holiday package at no cost if you've booked in the last 24 hours. For older bookings, you can still make the necessary changes, but your car rental company, hotel or airline may charge a fee. Want more information? Take a look at our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.

Activities

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
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

NZ$78
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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.