Prairie District Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,584, price is now CA $1,066 per person
CA $1,066
per person
Jul 3 - Jul 6
found 22 hours ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9/10 Wonderful! (472 reviews)
Beautiful clean place. Great safe location within proximity to restaurants and transportation around the city with fantastic views. Would recommend and stay here again.

Reviewed on May 14, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,016, price is now CA $1,256 per person
CA $1,256
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
This property has a great location. The hotel was really clean! We enjoyed the bar atmosphere, and we had a delicious appetizer! I will highly recommend this location for a great getaway for couples! Page at the front desk and Prudencia in housekeeping were amazing!

Reviewed on May 13, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $2,297, price is now CA $1,507 per person
CA $1,507
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.

Reviewed on May 8, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,764, price is now CA $1,183 per person
CA $1,183
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (471 reviews)
The rooms were very clean!

Reviewed on May 4, 2026

The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was CA $2,205, price is now CA $1,494 per person
CA $1,494
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
8.4/10 Very Good! (1,825 reviews)
Lovely hotel, very modern and clean. Had fantastic views from the top floor. We were on floor 28 and the skyline was great. Bed very comfortable and it was expected from a 4* hotel. Chicago is a business city, reminded me of a bar man set as its high rised buildings and slightly darker from the shadows of these buildings. Locally there was a few cafes and coffee shops for easy reach for breakfast

Reviewed on May 11, 2026

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

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 $183 per night from May 26 to May 27
CA $183
CA $218 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,118 reviews)
The room had an odor and eventhoufh it’s a landmark building with some renovations, there were not enough outlets, no coffee pot just sat on table nowhere near an outlet to plug up and make coffee. Complimentary water should be available not just $5 bottle in room. The hallways need air freshener. ...

Reviewed on May 14, 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from May 25 to May 26
CA $197
CA $234 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (5,173 reviews)
Hotel is a beautiful, smaller boutique property.

Reviewed on May 14, 2026

River 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 CA $194 per night from May 27 to May 28
CA $194
CA $270 total
May 27 - May 28
includes taxes & fees
9.4/10 Exceptional! (4,144 reviews)
This was my first time staying in a Riu Hotel and I was incredibly impressed. It was super clean, the staff was really helpful, and the breakfast was awesome. Five stars!!

Reviewed on May 14, 2026

Hotel Riu Plaza Chicago
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.
All Inclusive Vacations
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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 $1,066. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.