Title: Prairie District Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $876 Expedia.ca

[Prairie District Travel Guide](https://expedia.ca/Chicago-Prairie-District.dx553248635976473159)[Hotels in Prairie District](https://expedia.ca/Prairie-District-Chicago-Hotels.0-n553248635976473159-0.Travel-Guide-Filter-Hotels)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Prairie District Car Rentals](https://expedia.ca/Car-Rentals-In-Prairie-District.d553248635976473159.Car-Rental-Guide)

![](https://images.trvl-media.com/place/829/b48ccadb-3fe2-4b6d-9b7d-05a404bfb432.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Prairie District Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

Photo by Susie Morgan

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 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.

![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/bc751856_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

CA $876

per person

May 8 - May 11

found 4 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (356 reviews)

I loved they had breakfast, lunch and dinner. They also had an option if you wanted to get drinks, and snacks before heading up. The air conditioning keep the room cool.

Reviewed on Mar 27, 2026

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Chicago

Downtown Chicago

CA $999

per person

Jun 1 - Jun 4

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (3,495 reviews)

Everything was very nice. The room was very clean, amenities great, and staff friendly. Also, a great location less than a block off of Michigan Ave. Perfect for shopping! I would definitely stay here again.

Reviewed on Mar 28, 2026

![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,031

per person

Jun 1 - Jun 4

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,401 reviews)

Rooms are really nice and comfortable. View was awesome. Location is great, especially if you plan on spending a lot of time near navy pier. The noise level when you’re in your room is wonderful. No loud noises during the entire stay, which we greatly appreciated. The staff we experienced were not super helpful or friendly, and the phone in our room didn’t work. We were unable to contact guest services from our room, which was an annoyance. The restaurant was also not worth the hype. The food was expensive and the quality didn’t add up. While I have complaints, I’m still pleased with my stay overall, because of the cleanliness, convenience, and the room itself.

Reviewed on Mar 28, 2026

![The Chicago Hotel Collection - Wrigleyville](https://images.trvl-media.com/lodging/24000000/23610000/23604900/23604891/441ad9d1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Chicago Hotel Collection - Wrigleyville

Lakeview

CA $1,635

per person

May 2 - May 9

found 16 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

7/10 Good! (974 reviews)

Excellent location. Clean rooms

Reviewed on Mar 24, 2026

![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8c061e2a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago – Old Town

Downtown Chicago

CA $1,719

per person

Jun 18 - Jun 22

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

9/10 Wonderful! (441 reviews)

The rooms are extremely clean and have everything you need. The staff is so accommodating and friendly. The view is amazing

Reviewed on Mar 27, 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](https://expedia.ca/Chicago-Prairie-District.dx553248635976473159)

![Downtown Chicago](https://images.trvl-media.com/place/6350699/f8ae2db6-94cc-4898-aa46-e275588c3787.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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 hotel + flight trips in Downtown Chicago](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Chicago&DestID=6350699&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Magnificent Mile](https://images.trvl-media.com/place/800025/2f4bc1ac-f370-4b72-8a89-0aa7dcb93f0c.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Magnificent Mile

 Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service. 

[Find hotel + flight trips in Magnificent Mile](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Magnificent%20Mile&DestID=800025&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![The Loop](https://images.trvl-media.com/place/800024/9e323a45-98da-4519-b5ca-71275e70174f.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### The Loop

4.5/5(733 area reviews)

 Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago. 

[Find hotel + flight trips in The Loop](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=The%20Loop&DestID=800024&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Underground passage in the Chicago O'Hare airport](https://images.trvl-media.com/place/553248635074842747/1dda5453-2f05-4485-9f3c-404a7075d270.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### O'Hare

3.5/5(39 area reviews)

 Home to O'Hare International Airport, this transportation hub offers easy access to downtown via the Blue Line. The area also hosts various corporate headquarters and international consulates. 

[Find hotel + flight trips in O'Hare](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=O%27Hare&DestID=553248635074842747&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![River North](https://images.trvl-media.com/place/6350695/b009c703-f7ab-4e4c-95a4-4b883071adef.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### River North

 Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building. 

[Find hotel + flight trips in River North](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=River%20North&DestID=6350695&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Prairie District Hotel Deals

![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

CA $159

CA $187 total

Apr 5 - Apr 6

includes taxes & fees

8/10 Very Good! (10,004 reviews)

The website says the hotel offers Valet, it does not, apparently hasn’t since Covid… we just waited for someone to help with bags and to take the car, we had to go inside to find someone. The hallways walking to the room smelled, the room was updates in the main room, bathroom needs some updates ...

Reviewed on Mar 29, 2026

[](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true&regionId=553248635976473159)

![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/a215cd17_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Fully refundableReserve now, pay when you stay

CA $170

CA $199 total

Apr 6 - Apr 7

includes taxes & fees

9/10 Wonderful! (4,006 reviews)

Nice location and awesome room

Reviewed on Mar 29, 2026

[](https://expedia.ca/Hotel-Search?startDate=06%2F04%2F2026&endDate=07%2F04%2F2026&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true&regionId=553248635976473159)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/24d28405_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

Fully refundableReserve now, pay when you stay

CA $180

CA $211 total

Apr 12 - Apr 13

includes taxes & fees

8.6/10 Excellent! (5,792 reviews)

Great spot in the shopping district. Good breakfast and nice to have the snacks and drinks for the happy hour time.

Reviewed on Mar 28, 2026

[](https://expedia.ca/Hotel-Search?startDate=12%2F04%2F2026&endDate=13%2F04%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true&regionId=553248635976473159)

[See all 4,580 properties in Prairie District](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=30%2F03%2F2026&endDate=31%2F03%2F2026&regionId=553248635976473159)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## Frequently asked questions

### How much does a Prairie District vacation package cost?

### How do I get a cheap travel package to Prairie District?

### Where should I stay in Prairie District?

### How far in advance should I book my Prairie District vacation?

### What does an Expedia Prairie District travel package include?

### What should I know before booking a Prairie District travel package?

### Can I choose my airline with a Prairie District Expedia vacation package?

### If I'm not able to travel, can I cancel my Prairie District vacation package?

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.