Theatre District Holidays from £994

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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 Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
8.8/10 Excellent! (1,796 reviews)
The staff hospitality was incredible 💖

Reviewed on 2 Jul 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Amazing hotel with large rooms right off Michigan avenue. Staff is amazing, they are always friendly and helpful.

Reviewed on 27 Jun 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Staff was very friendly and helpful. We had a great stay in every way possible!

Reviewed on 30 Jun 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
Comfortable, stylish, friendly hotel in a fabulous location near Millennium Park, Art Institute, and Riverwalk. Friendly staff throughout but the cherry on top was Antoine who checked our bags and arranged out transportation to the airport when we checked out

Reviewed on 29 Jun 2025

Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
No reviews

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 featuring a city

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 hotels in Downtown Chicago

Top hotels in Theatre District

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 £116 per night from 7 Jul to 8 Jul
£116
7 Jul - 8 Jul
includes taxes & fees
9.2/10 Wonderful! (3,277 reviews)
"Such a"

Reviewed on 3 Jul 2025

citizenM Chicago Downtown
L7 Chicago by LOTTE
L7 Chicago by LOTTE
4.5 out of 5
225 N Wabash Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £154 per night from 10 Jul to 11 Jul
£154
10 Jul - 11 Jul
includes taxes & fees
9.6/10 Exceptional! (2,582 reviews)
"The staff was so kind. The room was amazing. Our new go-to for Chicago."

Reviewed on 2 Jul 2025

L7 Chicago by LOTTE
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £175 per night from 4 Aug to 5 Aug
£175
4 Aug - 5 Aug
includes taxes & fees
8.2/10 Very Good! (1,772 reviews)
"beautiful hotel, friendly and helpful staff."

Reviewed on 2 Jul 2025

Palmer House a Hilton Hotel
See all 4,425 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

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 £994. 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.

Popular places to visit

Chicago Theatre

Chicago Theatre

4/5(10 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
CIBC Theatre

CIBC Theatre

You can enjoy a show at CIBC Theatre on your trip to Chicago. Discover the acclaimed theatre scene and notable monuments in this vibrant area.

CIBC Theatre

Things to do

Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

£31
per adult
96% of travellers recommend
Chicago: Architecture Boat Tour with Drinks
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago River: 1.5-Hour Guided Architecture Riverboat Tour

Chicago River: 1.5-Hour Guided Architecture Riverboat Tour

£41
per adult
74% of travellers recommend
Chicago River: 1.5-Hour Guided Architecture Riverboat Tour
See all activities in Chicago

* 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.