Prairie District Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $959, price is now CA $616 per person
CA $616
per person
Oct 18 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
Pool area was great

Reviewed on Sep. 4, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $2,197, price is now CA $1,334 per person
CA $1,334
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!

Reviewed on Aug. 31, 2025

Art Villa

Art Villa

5 out of 5
West Town
Price was CA $3,005, price is now CA $1,922 per person
CA $1,922
per person
Oct 25 - Oct 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
10/10 Exceptional! (2 reviews)
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $2,153, price is now CA $1,389 per person
CA $1,389
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,028 reviews)
It was great for a short stay with my family. We enjoyed the location and proximity to public transportation.

Reviewed on Sep. 4, 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was CA $2,322, price is now CA $1,512 per person
CA $1,512
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on Aug. 12, 2025

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 showing 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

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 CA $204 per night from Sep 22 to Sep 23
CA $204
CA $240 total
Sep 22 - Sep 23
includes taxes & fees
Congress Plaza Hotel
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
Fully refundableReserve now, pay when you stay
The price is CA $246 per night from Sep 14 to Sep 15
CA $246
CA $288 total
Sep 14 - Sep 15
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $224 per night from Sep 14 to Sep 15
CA $224
CA $263 total
Sep 14 - Sep 15
includes taxes & fees
Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,492 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Prairie District vacation package cost?
We make it simple for everyone to travel, with Prairie District vacation packages starting from as low as CA $616. 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 vacation.
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 vacation?
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 vacation 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 vacation rentals such as beach villas and serviced residences. You've got choices galore!
Can I choose my airline with a Prairie District Expedia vacation 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 vacation package?
Your situation can change in a flash, so yes, you can. You may be able to cancel and rebook your Prairie District vacation 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.

Things to do

River tour boat in Chicago

Architecture River Tour

CA $67
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $62
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

CA $62
per adult
96% 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.