Theatre District Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    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.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 15 - Aug. 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
We celebrated a bachelorette party and stayed at this hotel. They were very accommodating to my requests and even greeted us with a welcome present! It made our stay that much better! Would definitely recommend this hotel.

Reviewed on May 22, 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 4 - Jul. 8
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (97 reviews)
Outstanding service and facility.

Reviewed on Jan. 10, 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 4 - Jul. 8
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (687 reviews)
This is probably the very best location to stay when visiting Chicago. A beautiful old Art Deco building that has been beautifully maintained. We loved staying here. Easy walk to everything.

Reviewed on May 25, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 15 - Aug. 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,190 reviews)
Great view and environment

Reviewed on May 23, 2024

Ambassador Chicago, part of JdV by Hyatt

Ambassador Chicago, part of JdV by Hyatt

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 31 - Aug. 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
In the area I wanted to be near

Reviewed on May 23, 2024

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
Downtown Chicago showing a city

Downtown Chicago

4 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 Navy Pier and Millennium Park are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips in Downtown Chicago

Theatre District Hotel Deals

Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from May 27 to May 28
CA $193
CA $227 total
includes taxes & fees
May 27 - May 28
8.4/10 Very Good! (3,062 reviews)
"Small room"

Reviewed on May 25, 2024

Club Quarters Hotel, Central Loop, Chicago
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from May 27 to May 28
CA $144
CA $169 total
includes taxes & fees
May 27 - May 28
9.2/10 Wonderful! (1,378 reviews)
"Luv the cool designs in the building"

Reviewed on May 23, 2024

citizenM Chicago Downtown
Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago Downtown
4 out of 5
10 S Wabash Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $245 per night from May 27 to May 28
CA $245
CA $319 total
includes taxes & fees
May 27 - May 28
9.2/10 Wonderful! (1,607 reviews)
"Great hotel"

Reviewed on May 25, 2024

Silversmith Hotel Chicago Downtown
See all 4,077 properties in Theatre 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Theatre District vacation package cost?
We make it simple to travel the world, with Theatre District packages starting from as little as CA $851. You’ll have the flexibility to bundle your favorite hotels, airlines and car rental. For the ultimate getaway, why not add some activities and tours to your itinerary?
How do I get a cheap travel package to Theatre District?
One of the simplest ways to save dollars (and time) is to bundle your bookings with Expedia. Flights, hotels, rental cars and activities — we’ve got it all. Select a combination that best fits you and see your savings pile up. We know a package deal is never one-size-fits-all. That’s why we offer more than 550 partner airlines and 1,000,000 hotel options across the globe, which lets you customize your Theatre District getaway.
Where should I stay in Theatre District?
Urban adventurers come from all over the world to see McCormick Place and Millennium Park in Theatre District. Book yourself a room within a stone’s throw of these must-see attractions to make sightseeing easy.
What are the top hotels in Theatre District?
Hotel Julian and Kimpton Hotel Monaco Chicago, an IHG Hotel are among the most well-known hotels in Theatre District. Why not have a look at the amenities and facilities at each and then make a decision?
How far in advance should I book my Theatre District vacation?
Reserving your flight early with Expedia means one less thing to worry about. Many air carriers advertise prices up to 12 months in advance. This is often the cheapest time to book. If circumstances have left you booking late, great deals to Theatre District are still known to appear in the weeks leading up to departure.
What does an Expedia Theatre District travel package include?
That depends on what you’re after. If you’re traveling alone, you might decide to combine hotels and flights. Taking the whole family to Theatre District? A travel package that includes flights, hotels and rental cars might suit you better. Expedia gives you the flexibility to tailor your travel package.
What should I know before booking a Theatre District travel package?
When you book your flights, hotels and car rentals together, you’ll nab great discounts. Whether you’re planning an island getaway in a villa or prefer to stay in a cozy apartment in the city, Expedia will help make it happen.
Can I choose my airline with a Theatre District Expedia vacation package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines throughout the world. Our vacation packages give you the freedom to pick from available flights, hotels and activities that fit your needs.
If I'm not able to travel, can I cancel my Theatre District vacation package?
Yes, you can. We understand that things don’t always go to plan, so we’re happy to help if you need to make changes to your Theatre District vacation package. You may be able to cancel or amend your itinerary at no cost if you’ve booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Head to our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Theatre District

Image for Chicago Theatre

Chicago Theatre

4.5/5(73 reviews)

See a stage show at this iconic cultural beacon, which still captures all the splendor of a trip to the movie theater in the early 20th century.

Chicago Theatre
Image for Cadillac Palace Theatre

Cadillac Palace Theatre

You can get tickets for a performance at Cadillac Palace Theatre during your stay in Chicago. Discover the acclaimed theater scene and notable monuments in this vibrant area.

Cadillac Palace Theatre
Image for CIBC Theatre

CIBC Theatre

You can get tickets for a performance at CIBC Theatre on your trip to Chicago. Discover the acclaimed theater scene and notable monuments in this vibrant area.

CIBC Theatre

Things to do

Image for Chicago Pizza Tour

Chicago Pizza Tour

CA $121
Per adult
100% of travellers recommend
Chicago Pizza Tour
Image for Chicago: City Minibus Tour with Optional Architecture Cruise

Chicago: City Minibus Tour with Optional Architecture Cruise

CA $64
Per adult
98% of travellers recommend
Chicago: City Minibus Tour with Optional Architecture Cruise
Image for Chicago C3® by CityPASS®

Chicago C3® by CityPASS®

CA $138
Per adult
78% of travellers recommend
Chicago C3® by CityPASS®
See all activities in Chicago

Other vacations you might like

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