Prairie District Holidays from NZ$5,549

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Top Holiday Package Deals in Prairie District

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
per person
15 Aug - 18 Aug
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
8.2/10 Very Good! (2,069 reviews)
Item was left in room. I tried for days to get contact with front desk and security will little to no luck. They say nothing reported so I consider that as theft by staff. Very disappointing.

Reviewed on 2 Jul. 2025

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,840 reviews)
Absolutely loved the staff! The hotel was clean & quiet. I will definitely recommend it and I’ll be returning.

Reviewed on 4 Jul. 2025

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (1,917 reviews)
Even after renovation rooms are still looking dated

Reviewed on 4 Jul. 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (3,353 reviews)
Everything is close that's make my day perfect.

Reviewed on 5 Jul. 2025

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Downtown Chicago
per person
15 Aug - 18 Aug
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
8.4/10 Very Good! (4,263 reviews)
The room was very spacious and clean. We arrived late and the staff was not very helpful; just did the basics and left us to figure out the rest. The breakfast was good, but stressful because of the set up and amount of people. I think there may have been some sort of dinner option, but we were explained that at check-in, so I'm not too sure, but we saw people eating. The website says $79 valet available, but it's basically required because there is no option for street parking. The hotel is very close to everything and because of it, it's a very busy area. We stayed with children and would have preferred to stay in a more family friendly area.

Reviewed on 4 Jul. 2025

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 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 hotels in Downtown Chicago

Our pick of the best Prairie District Hotel Deals

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$308 per night from 7 July to 8 July
NZ$308
7 July - 8 July
includes taxes & fees
8.8/10 Excellent! (2,377 reviews)
"Friendly staff, beautiful views, excellent location"

Reviewed on 5 Jul. 2025

Hilton Chicago/Magnificent Mile Suites
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is NZ$494 per night from 7 July to 8 July
NZ$494
7 July - 8 July
includes taxes & fees
9/10 Wonderful! (1,967 reviews)
"It was our first time in staying in Chicago and we couldnt have picked a better resort!!"

Reviewed on 3 Jul. 2025

InterContinental Chicago Magnificent Mile by IHG
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$277 per night from 4 Aug to 5 Aug
NZ$277
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (8,863 reviews)
"Decent stay for a few nights"

Reviewed on 3 Jul. 2025

Congress Plaza Hotel
See all 4,395 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$5,549. 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

River tour boat in Chicago

Architecture River Tour

NZ$81
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

NZ$75
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

NZ$75
per adult
92% of travellers recommend
Chicago By Night River & 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.