Title: Theatre District Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $460 Expedia.ca

[Theatre District Travel Guide](https://expedia.ca/Chicago-Theatre-District.dx651190586167894016)[Hotels in Theatre District](https://expedia.ca/Theatre-District-Chicago-Hotels.0-n651190586167894016-0.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)[Theatre District Car Rentals](https://expedia.ca/Car-Rentals-In-Theatre-District.d651190586167894016.Car-Rental-Guide)

![](https://images.trvl-media.com/place/829/1a8abde0-c15d-4b25-9c4c-74d2678f7428.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Theatre District Vacation Packages

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

Photo by Betina Winsig Hansen

- ##  
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Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
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Rest easy  
Plan, book, and manage your trip all in one place

## Top Holiday Package Deals in Theatre District

Price found within the past 48 hours. Click for updated prices.

![Red Roof Inn PLUS+ Chicago - Willowbrook](https://images.trvl-media.com/lodging/1000000/10000/4100/4013/dd62fe20_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Red Roof Inn PLUS+ Chicago - Willowbrook

CA $460

per person

Apr 11 - Apr 16

found 21 hours ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

6.4/10 (1,004 reviews)

Check in was quick and simple. The room was clean and that's all i needed for a few hours until i went to the airport. The extra lock on the,door was broken. There also was a coffee pot, but no coffee in the room

Reviewed on Feb 8, 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 $712

per person

Apr 30 - May 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Best location, breakfast is excellent

Reviewed on Feb 13, 2026

![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago Fulton Market

Downtown Chicago

CA $799

per person

Apr 23 - Apr 26

found 10 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (347 reviews)

Hot tub wasn’t working(freezing cold) and no robes in my room. Need bigger roller carts and cheaper or free parking. Other than that the room, view, amenities were excellent.

Reviewed on Feb 9, 2026

![JW Marriott Chicago](https://images.trvl-media.com/lodging/4000000/3540000/3538400/3538327/232aa080_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### JW Marriott Chicago

Downtown Chicago

CA $723

per person

Apr 30 - May 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,000 reviews)

Bottle of waters were not stocked in the refrigerator.

Reviewed on Jan 6, 2026

![Stay One Chicago](https://images.trvl-media.com/lodging/113000000/112870000/112868000/112867973/0bd05cf3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Stay One Chicago

Downtown Chicago

CA $2,385

per person

Apr 28 - May 4

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

No reviews

The property was great, the room was awesome! The "Stay One Chicago" is really just a name on paper, and maybe one employee who is physically at the property. I am pretty sure that he wasn't even directly employed by the "hotel". So in a nutshell, the organization has not worked out any kind of structure for checking in other than the guy that told us to download the Door, OR the Latch app. He said that the app is very difficult to get logged into. Long story made short, we wasted the 1st 2 hours in the hotel trying to get the app (both my wife and I). The app never worked, and we finally got physical key cards from the guy working for the building. There was one small piece of paper with scan codes for restaurants, but zero property maps, rules, room cleaning, and nothing explaining how to get to, or use any of the amenities. It was the worst 1st 3 hours of a vacation that we have experienced. I still gave it a 4-star because the local people were so nice and helpful, even though helping us wasn't part of their job. The valet guys were the best, super nice, and helpful.

Reviewed on Feb 10, 2026

## Where to stay in Theatre District

Find the best Theatre District areas and neighborhoods for the activities you enjoy most. [Learn more about Theatre District](https://expedia.ca/Chicago-Theatre-District.dx651190586167894016)

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

### Downtown Chicago

4 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 - River North](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 - Downtown featuring a river or creek](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(725 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)

![River North showing railway items, street scenes and a city](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)

![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(38 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)

## Theatre District Hotel Deals

![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL

Fully refundableReserve now, pay when you stay

CA $183

CA $249 total

Feb 21 - Feb 22

includes taxes & fees

8.4/10 Very Good! (2,283 reviews)

Housekeeping staff was great

Reviewed on Feb 13, 2026

[](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=8079&PinnedHotelID=8079&HadPinnedHotel=true&regionId=651190586167894016)

![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

theWit Chicago, a Hilton Hotel

201 N State Street Chicago IL

Fully refundableReserve now, pay when you stay

CA $189

CA $262 total

Feb 22 - Feb 23

includes taxes & fees

8.8/10 Excellent! (1,003 reviews)

Stayed at the Wit one night to see a show nearby. The hotel was busy but the staff was accommodating and wonderful, the rooftop bar was hopping and the food, drinks and sevice was great! The rooms were very clean. The State and Lake restaurant in the hotel we visited for breakfast and it has a very ...

Reviewed on Feb 7, 2026

[](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=2463437&PinnedHotelID=2463437&HadPinnedHotel=true&regionId=651190586167894016)

![L7 Chicago by LOTTE](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/6dfbfa42_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

L7 Chicago by LOTTE

225 N Wabash Ave Chicago IL

CA $186

CA $219 total

Feb 15 - Feb 16

includes taxes & fees

9.6/10 Exceptional! (3,643 reviews)

Staff was welcoming and extremely helpful. The room was clean and beautiful. Had a great view of the river

Reviewed on Feb 11, 2026

[](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=4200&PinnedHotelID=4200&HadPinnedHotel=true&regionId=651190586167894016)

[See all 4,697 properties in Theatre District](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&regionId=651190586167894016)

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 Theatre District vacation package cost?

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

### Where should I stay in Theatre District?

### What are the top hotels in Theatre District?

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

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

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

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

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

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