Theatre District Holidays from £1,024

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,393, price is now £1,024 per person
£1,024
per person
27 Aug - 31 Aug
found 12 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
Modern interior design of the lobby and cleanliness of the room.

Reviewed on 14 Jun 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was £1,880, price is now £1,326 per person
£1,326
per person
28 Aug - 4 Sept
found 12 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9/10 Wonderful! (484 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.

Reviewed on 11 Jun 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was £1,650, price is now £1,211 per person
£1,211
per person
31 Jul - 4 Aug
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,325 reviews)
Rooftop Movie theater looked fun during the daytime, but wasn’t committed enough to buy a ticket after sunset. Rooms were fine. Coffee shop was short-staffed the day I was there - to the point I gave up and moved on. The staff I ran into in the hotel from housekeeping to front desk to bell staff were all universally pleasant and helpful. Location was great - convenient to the show I was attending at the Cobra Lounge and to a pretty decent variety of decent looking food options. Don’t miss the Hubbard St viaducts on your morning walk.

Reviewed on 8 Jun 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £1,771, price is now £1,327 per person
£1,327
per person
31 Jul - 4 Aug
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
The hotel was wonderful. Everything was extremely clean, the entire staff was very friendly, and the service was exceptional. We had the best experience

Reviewed on 14 Jun 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was £1,736, price is now £1,304 per person
£1,304
per person
31 Jul - 4 Aug
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,735 reviews)
Perfect location. Very clean.

Reviewed on 14 Jun 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

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

Arlo Chicago

Arlo Chicago

4 out of 5
168 N Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is £198 per night from 5 Jul to 6 Jul
£198
5 Jul - 6 Jul
includes taxes & fees
9.4/10 Exceptional! (2,153 reviews)
"Great location to take in the sites of Chicago! Bar staff were great! Confusion around getting my room cleaned and when the “do not disturb” sign was or wasn’t on the door preventing cleaning. But if they ever get that sorted out, they’ll be great!"

Reviewed on 13 Jun 2026

Arlo Chicago
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 £265 per night from 2 Jul to 3 Jul
£265
2 Jul - 3 Jul
includes taxes & fees
9.6/10 Exceptional! (4,179 reviews)
"Clean, well-maintained room with some extra perks such as facial mask, yoga mat, etc. The staff are all friendly and welcoming! Great location!"

Reviewed on 15 Jun 2026

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 £185 per night from 30 Jun to 1 Jul
£185
30 Jun - 1 Jul
includes taxes & fees
8.6/10 Excellent! (2,508 reviews)
"The staff were all very professional and nice from the valet parking, registration, etc. We got a King Size bedroom. We were offered a better option for additional amount but declined. It was one of the older non renovated rooms and I am with, in preserving the character but the closet door handle ..."

Reviewed on 14 Jun 2026

Palmer House a Hilton Hotel
See all 4,541 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.
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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 £1,024. 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
Open Photo by © Choose Chicago

Chicago Theatre

4.5/5 (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.
See properties

* 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.