Prairie District Holidays

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
Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Aug 13 - Aug 18

    The Westin Chicago Lombard + Flight

    Lombard
    5 nights
    4.0 star property
    9.0/10 - Wonderful (1,254 reviews)
    "Requested a room with a walk in shower as I have a broken foot and am wearing a walking boot. Was told none were available but online through the hotels own website it showed they were and were bookable for my entire stay. Rude front desk staff. Probably will never stay there again. This hotel has gone down hill for sure"
    Reviewed May 25, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$3,314
    NZ$2,826
    per traveller
    found 18 hours ago
    The Westin Chicago Lombard
  • 55-inch TV with cable channels, video game console, pay films
    Aug 12 - Aug 17

    Hilton Chicago O'Hare Airport + Flight

    O'Hare
    5 nights
    4.0 star property
    8.4/10 - Very good (2,303 reviews)
    "No complaints"
    Reviewed May 28, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$4,056
    NZ$3,237
    per traveller
    found 18 hours ago
    Hilton Chicago O'Hare Airport
  • Coffee shop
    Aug 12 - Aug 17

    Hilton Rosemont Chicago O'Hare + Flight

    Rosemont
    5 nights
    3.5 star property
    8.4/10 - Very good (1,000 reviews)
    "Great"
    Reviewed May 25, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$4,302
    NZ$3,509
    per traveller
    found 18 hours ago
    Hilton Rosemont Chicago O'Hare
  • Bar (on property)
    Aug 12 - Aug 17

    Embassy Suites by Hilton Chicago O'Hare Rosemont + Flight

    Rosemont
    5 nights
    4.0 star property
    8.8/10 - Excellent (1,392 reviews)
    "Good!"
    Reviewed May 26, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$3,674
    NZ$3,097
    per traveller
    found 18 hours ago
    Embassy Suites by Hilton Chicago O'Hare Rosemont
  • Exterior
    Aug 12 - Aug 17

    Holiday Inn Express & Suites Chicago O'Hare Airport by IHG + Flight

    Des Plaines
    5 nights
    3.0 star property
    8.8/10 - Excellent (1,853 reviews)
    "Very friendly staff, room was super clean and lots of nearby restaurants and 5 minutes from airport. Great location!"
    Reviewed May 29, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$3,349
    NZ$2,834
    per traveller
    found 18 hours ago
    Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

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
Downtown Chicago

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

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$261 per night from 29 June to 30 June
NZ$261
29 June - 30 June
includes taxes & fees
8/10 Very Good! (10,124 reviews)
"Great location and clean"

Reviewed on 29 May 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$479 per night from 29 June to 30 June
NZ$479
29 June - 30 June
includes taxes & fees
9.4/10 Exceptional! (4,287 reviews)
"Nice place"

Reviewed on 29 May 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is NZ$304 per night from 28 June to 29 June
NZ$304
28 June - 29 June
includes taxes & fees
7.8/10 Good! (1,486 reviews)
"The hotel was amazing looked exactly like the photos. The staff was awesome 10/10 I would for sure stay here again!"

Reviewed on 29 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,592 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 . 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.

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$45
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

NZ$74
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

NZ$77
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.