Theatre District Holidays from £1,450
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Your Theatre District Holiday
Leap into your next thrilling adventure with one of our Theatre District holiday packages. Spend your time getting to know this neighbourhood's countless charms, such as its culture. Hoping to do some sightseeing during your trip to Theatre District? Pencil in a visit to nearby attractions such as Millennium Park, Willis Tower and Art Institute of Chicago. Expedia can help you turn your ideal Theatre District holiday into reality, no matter your budget or travel plans.
Price found within the past 48 hours. Click for updated prices.
The Drake
Downtown Chicago
£1,450
per person
8 Nov - 12 Nov
found 16 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (1,583 reviews)
Non-operable refrigerator that had to be replaced. Poorly functioning shower. Limited amount of conditioner that was not sufficient for two girls with long hair. No body wash. Definitely disappointing.
Reviewed on 23 Sept 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.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in Theatre District
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
172 W Adams St Chicago IL
Fully refundableReserve now, pay when you stay
£120
27 Sept - 28 Sept
includes taxes & fees
L7 Chicago by LOTTE
225 N Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
£256
27 Sept - 28 Sept
includes taxes & fees
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
Fully refundableReserve now, pay when you stay
£216
23 Oct - 24 Oct
includes taxes & fees
9/10 Wonderful! (2,915 reviews)
"I absolutely loved this hotel. It felt so luxurious and was in the perfect location. I absolutely loved staying here and will recommend it to all friends and family who would like to take a journey to Chicago."
Reviewed on 23 Sept 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 travel package cost?
Choose from any combination of car rentals, flights and hotels, and you can be holidaying in Theatre District from just £1,450. And the more you bundle, the more you save. Your dream holiday has never been more affordable.
If I'm not able to travel, can I cancel my Theatre District travel package?
Plans can change without warning, so yes. You may be able to cancel or amend your Theatre District travel 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 impose a fee. Want more information? Check out our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.
How do I get a cheap travel package to Theatre District?
It's easy. Just bundle. Hotels, rental cars and flights — combine whatever you need into a Theatre District travel package to save a ton of cash. Score even better deals when you include extras such as sightseeing tours to your booking. But that's not the only good part. You have the flexibility to customize your holiday your own way. We offer more than 550 airlines and 1,000,000 hotel options throughout the world, so that everyone has an opportunity to travel and fulfil those holiday fantasies.
Does Expedia offer Book Now, Pay Later Theatre District holidays?
We do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply choose the payment plan best suited to your needs during the checkout process and take the stress out of budgeting for your next trip. Remember to bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your travel buck. Browse our flexible payment options below:
- Pay monthly holidays: Klarna offers easy monthly payment plans that work for all types of budgets, so you can take that well-deserved holiday now.
- Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay off your holiday across multiple transactions.
- Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to hit that "book now" button, go for a low deposit holiday payment plan from Klarna.
Where should I stay in Theatre District?
A journey to Theatre District isn't complete without stopping by Millennium Park and Wrigley Field. Reserve a room nearby and easily access these fantastic sights.
What are the top hotels in Theatre District?
Get your holiday off to a fantastic start by staying at Hyatt Regency Chicago. It's one of most sought-after properties in Theatre District. Another welcoming option is The Godfrey Hotel Chicago.
How far in advance should I book my Theatre District holiday?
While prices fluctuate, we generally recommend reserving your seat as early as possible. Many international airfares are found on Expedia up to a year in advance. If you're booking last minute, you might still be in luck. Discount prices to Theatre District sometimes occur just weeks before departure.
What does an Expedia Theatre District travel package include?
Flights, rental cars and hotels — we've got them all. With Expedia, you can create your Theatre District package however you want. All you have to do is decide what you need. Once you've made your booking, you can add on fun things like experiences and activities. The more you bundle, the bigger the savings!
What should I know before booking a Theatre District travel package?
You'll enjoy amazing savings when you combine your flights, hotels and rental cars into a travel package. Plus, booking everything together simply makes planning easier. So why waste your time or money? Whether you're putting together a fancy romantic getaway or a low-cost family break, check out our travel packages today.
Can I choose my airline with a Theatre District Expedia travel package?
Expedia has access to more than 550 partner airlines worldwide, so you certainly can. Simply choose your favourite carrier and put together your ideal Theatre District escape.
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.
Photo by TM
Chicago Cultural Center
9.2/10 (220 reviews)
Enjoy a stop at Chicago Cultural Center, an entertaining place to visit in Chicago. Discover the fascinating museums and notable monuments in this vibrant area.
Photo by F Cast@72
CIBC Theatre
8.4/10 (52 reviews)
You can enjoy a show at CIBC Theatre on your trip to Chicago. Discover the fascinating museums 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 entertainment choices in this vibrant area.
Daley Plaza
8.0/10 (4 reviews)
You can learn about the history of Chicago when you stop by Daley Plaza. Experience the fascinating museums and entertainment choices 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 on your trip to Chicago. Discover the acclaimed art galleries and notable monuments in this vibrant area.
Photo by LJ Alan
Chicago Board of Trade Building
10.0/10 (2 reviews)
You can learn about the history of Chicago when you stop by Chicago Board of Trade Building. Experience the acclaimed theatre scene and fascinating museums in this vibrant area.
Goodman Theater
You can enjoy a show at Goodman Theater during your stay in Chicago. Amble around this vibrant area's riverfront or experience its acclaimed theatre scene.
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
£35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
£18
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.