Theatre District Vacation Packages
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Top Holiday Package Deals in Theatre District
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,106
per person
Sep 21 - Sep 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Expected more honestly from rave reviews but was just ok. Family “deluxe” suite- just a regular room with a sofa bed. Amenities average. Requests ignored. No late check out without hourly charge. Basically an average level property in a great location for quite a high price
Reviewed on Aug 7, 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
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.
The Loop
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.
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.
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.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Theatre District Hotel Deals
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
Fully refundableReserve now, pay when you stay
CA $226
CA $313 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (2,731 reviews)
"Outdated except for TV and bed."
Reviewed on Aug 7, 2026
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street Chicago IL
Fully refundable
CA $167
CA $199 total
Aug 9 - Aug 10
includes taxes & fees
8.8/10 Excellent! (3,619 reviews)
"Our room was very comfortable and clean. We were a little disappointed that there was no dresser or luggage rack. That made it a little difficult as there was no way to unpack and no place to put our clothing. Otherwise, the place is great! There is a guest closet with small items like toothpaste ..."
Reviewed on Aug 7, 2026
L7 Chicago by LOTTE
225 N Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
CA $249
CA $296 total
Aug 9 - Aug 10
includes taxes & fees
9.6/10 Exceptional! (4,518 reviews)
"The location ,clean and staff was perfect."
Reviewed on Aug 7, 2026
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.
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 $751. 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.
Stay near popular Theatre District attractions
Photo by © Choose Chicago
Chicago Theatre
9.0/10 (1,866 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 Cultural Center
9.2/10 (220 reviews)
Enjoy a stop at Chicago Cultural Center, an entertaining place to visit in Chicago. Discover the acclaimed art scene and notable monuments in this vibrant area.
Photo by F Cast@72
CIBC Theatre
8.4/10 (52 reviews)
You can get tickets for a performance at CIBC Theatre on your trip to Chicago. Discover the acclaimed art scene and notable monuments in this vibrant area.
Photo by Meghan hernandez
Cadillac Palace Theatre
8.0/10 (1 review)
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.
Chicago City Hall
9.0/10 (10 reviews)
Chicago City Hall is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or experience the acclaimed art scene in this vibrant area.
Daley Plaza
8.0/10 (4 reviews)
You can learn about the history of Chicago with a visit to Daley Plaza. Experience the fascinating museums and acclaimed art scene in this vibrant area.
Goodman Theater
You can enjoy a show at Goodman Theater on your trip to Chicago. Amble around this vibrant area's riverfront or experience its entertainment choices.
James M. Nederlander Theatre
9.2/10 (10 reviews)
You can make plans for a show at James M. Nederlander Theatre during your trip to Chicago. Stroll along the riverfront or visit the notable monuments in this vibrant area.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.