Prairie District Holidays from NZ$3,234

Book a Hotel + Flight or Car together to unlock savings

Photo by Susie Morgan

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Prairie District

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Price was NZ$4,009, price is now NZ$3,234 per person
NZ$3,234
per person
5 Sept - 11 Sept
found 16 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.4/10 Very good! (3,939 reviews)
It needs to be refreshed it’s drab and dreary and doesn’t look clean my bathroom was dangerous I don’t need a handicap accessible but there are no bars to hang on to getting in and out of shower just depressing and breakfast a joke 1 morning no protein at all

Reviewed on 13 July 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$4,324, price is now NZ$3,433 per person
NZ$3,433
per person
5 Sept - 11 Sept
found 16 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
While amenities and being up to date are important, my main focus for a hotel is it’s cleanliness and how comfortable is the bed since I’ve stayed many places that while nice, if the bed is uncomfortable can ruin your stay. Our room at Omni was clean and comfortable. There were a few things that looked a little tired and could use updating but overall we had a good sleep and were refreshed for the next day.

Reviewed on 13 July 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was NZ$4,833, price is now NZ$3,853 per person
NZ$3,853
per person
5 Sept - 11 Sept
found 16 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (3,764 reviews)
Well I thought I had a suite taco g the river but I only saw old fan boxes on top of buildings… I asked to switch rooms… they said there was an up charge which would’ve been fine but the more expensive room was mush smaller than the one facing the buildings…. Highly disappointed!! In addition.. there are no microwaves on the premises but there is a refrigerator … don’t make plans to bring back leftovers because there is NO WHERE to reheat them… for the money paid to stay here they lacked basic necessities..

Reviewed on 13 July 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was NZ$4,532, price is now NZ$3,677 per person
NZ$3,677
per person
5 Sept - 11 Sept
found 16 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.8/10 Excellent! (2,239 reviews)
Staff are wonderful. Room was nice. The “sofa” in the room was a piece of wood with cushions on it, not what I expected. The room was great size. Location is ideal for my girls trip.

Reviewed on 13 July 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was NZ$4,526, price is now NZ$3,710 per person
NZ$3,710
per person
5 Sept - 11 Sept
found 16 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (3,435 reviews)
The bat was awesome!

Reviewed on 13 July 2026

Our guide on where to stay in Prairie District

Find the best Prairie District areas and neighborhoods for the activities you enjoy most. Learn more about Prairie District
A busy city street with tall buildings, a bus, and cars.

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 Prairie District Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is NZ$334 per night from 5 Aug to 6 Aug
NZ$334
5 Aug - 6 Aug
includes taxes & fees
8.8/10 Excellent! (2,838 reviews)
"I booked a room for my mother and I and we loved it!! The staff there were all very helpful and the hotel was well kept and clean! One complaint I have is that there were no luggage carts anywhere to be found, made checkout a bit difficult. Overall a 4.5/5"

Reviewed on 13 July 2026

Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$339 per night from 27 July to 28 July
NZ$339
27 July - 28 July
includes taxes & fees
8.2/10 Very good! (1,745 reviews)
"The property is located near the beach and restaurants. It’s ideal for accessibility. Unfortunately our hotel room shower was broken. The bathroom was in poor condition and had not been maintained."

Reviewed on 13 July 2026

The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$543 per night from 26 July to 27 July
NZ$543
26 July - 27 July
includes taxes & fees
9.2/10 Wonderful! (1,917 reviews)
"While amenities and being up to date are important, my main focus for a hotel is it’s cleanliness and how comfortable is the bed since I’ve stayed many places that while nice, if the bed is uncomfortable can ruin your stay. Our room at Omni was clean and comfortable. There were a few things that ..."

Reviewed on 13 July 2026

Omni Chicago Hotel
See all 4,370 properties in Prairie District
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 Prairie District holiday package cost?
We make it simple for everyone to travel, with Prairie District holiday packages starting from as low as NZ$3,234. You'll have the flexibility to bundle your preferred hotels, airlines and car rental. For the ultimate getaway, why not add some activities and tours to your travel itinerary?
How do I get a cheap travel package to Prairie District?
One of the simplest ways to save cash (and time) is to combine your bookings with Expedia. Hotels, rental cars, flights and activities — we've got them all covered. Pick and choose the combination that best suits you and watch your savings stack up. We know a travel package is never one-size-fits-all. That's why we offer over 550 partner airlines and 1 000 000 properties globally, which lets you customize your Prairie District holiday.
Where should I stay in Prairie District?
Most visitors to Prairie District put both McCormick Place and Millennium Park on their bucket lists. Why not choose a hotel that's close to these great attractions?
How far in advance should I book my Prairie District holiday?
Your safest bet is to book early. Airlines typically advertise flight tickets nearly 12 months prior to departure, and this is a perfect opportunity to score some of the cheapest prices. Just been told you need to take your holiday time next month? No sweat. Expedia are never short on fantastic deals to whisk you away on the getaway of your dreams, at an affordable price.
What does an Expedia Prairie District travel package include?
Expedia has all you need to lock in Prairie District escape, but how you structure your package depends on you. Pick from a combination of flights, rental cars and hotels. Chasing some tours or experiences to keep you on the go? Once you've made your booking, you can add them too. Whatever your budget, there's a deal to meet your needs.
What should I know before booking a Prairie District travel package?
Locking in all the parts of your getaway together is an excellent way to save. Bundle your 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 such as beach villas and serviced residences. You've got choices galore!
Can I choose my airline with a Prairie District Expedia holiday package?
Yes, you're in charge. We have access to over 550 partner airlines across the globe, so you can tailor your Prairie District escape according to your needs and budget.
If I'm not able to travel, can I cancel my Prairie District holiday package?
Your situation can change in a flash, so yes, you can. You may be able to cancel and rebook your Prairie District holiday package for free within 24 hours of booking. For older bookings, you can still make changes, but your car rental company, airline or hotel may charge a fee. Want more information? Check out our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.

Stay near popular Prairie District attractions

Glessner House Museum

You can spend time exploring the galleries in Glessner House Museum during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.
See properties

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$48
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

NZ$70
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

NZ$43
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel 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.