Theatre District Holidays from £445

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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
Price was £675, price is now £445 per person
£445
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
Check in and out was seamless! Got excellent help with bags and access to amenities! Great location it was about a 9 min walk to Riverwalk, Hop on Bus; felt safe and area was clean

Reviewed on 18 Aug 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,890, price is now £1,141 per person
£1,141
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9/10 Wonderful! (654 reviews)
I always enjoy my stay

Reviewed on 18 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,385, price is now £839 per person
£839
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,050, price is now £669 per person
£669
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
Rooms are basic and bathrooms and sink area small. But all comfortable

Reviewed on 17 Aug 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,769, price is now £1,162 per person
£1,162
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,341 reviews)
No hot water in the shower for the entirety of our 3 night stay, it was barely warm. Complained multiple times, other guests were also facing the same problem. The responses ranged from "engineers are working on it" to "leave the water running for longer" to finally "that is the hottest water you're going to get". That was unbelievable given that the sink had hotter water than the shower. Upon my insistence, they offered to move us to a different room the next day after 3pm - that meant we would have had to take cold showers for 2 days. In the end we just didn't take up the moving-rooms hassle in the middle of our trip.

Reviewed on 18 Aug 2025

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

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 £169 per night from 3 Sept to 4 Sept
£169
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (1,871 reviews)
"It’s a beautiful hotel with lovely staff. The beds were very comfy but the pillows have no neck support. We loved how close it was to Millennium park and how walkable the area was for finding dining options and seeing the sights. It’s only about one city block from the Art Institute and we got to ..."

Reviewed on 18 Aug 2025

Palmer House a Hilton Hotel
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
The price is £125 per night from 24 Aug to 25 Aug
£125
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (3,601 reviews)
"Good"

Reviewed on 18 Aug 2025

citizenM Chicago Downtown
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £153 per night from 2 Sept to 3 Sept
£153
2 Sept - 3 Sept
includes taxes & fees
8.8/10 Excellent! (1,954 reviews)
"Check in and out was seamless! Got excellent help with bags and access to amenities! Great location it was about a 9 min walk to Riverwalk, Hop on Bus; felt safe and area was clean"

Reviewed on 18 Aug 2025

The Allegro Royal Sonesta Hotel Chicago Loop
See all 4,556 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 £445. 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

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 art galleries 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
88% 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
86% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

£79
per adult
86% of travellers recommend
Chicago C3® by CityPASS®
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.