Theatre District Holidays from £719

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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.
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was £898, price is now £719 per person
£719
per person
20 Jan - 24 Jan
found 7 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
Not worth it for the money. Good location but nothing special.

Reviewed on 8 Nov 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £1,797, price is now £1,324 per person
£1,324
per person
25 Dec - 30 Dec
found 6 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
The hotel is well located, walkable to magnificent mile, shops, restaurants and the River. The spacious room was on a high floor with high ceilings and an incredible view. The amenities were very nice and the room was impeccable.

Reviewed on 8 Nov 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £1,091, price is now £818 per person
£818
per person
20 Jan - 24 Jan
found 7 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.

Reviewed on 8 Nov 2026

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was £1,079, price is now £841 per person
£841
per person
11 Jan - 16 Jan
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was £1,202, price is now £955 per person
£955
per person
20 Jan - 24 Jan
found 7 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,309 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
A busy city street with tall buildings, a bus, and cars.

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.

Find hotels in Downtown Chicago

Top hotels in Theatre District

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
172 W Adams St Chicago IL
Fully refundableReserve now, pay when you stay
The price is £106 per night from 3 Dec to 4 Dec
£106
3 Dec - 4 Dec
includes taxes & fees
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
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 £116 per night from 25 Nov to 26 Nov
£116
25 Nov - 26 Nov
includes taxes & fees
9.6/10 Exceptional! (5,201 reviews)
"a great hotel. second time we have stayed location is excellent . staff is great. rooms are nice size"

Reviewed on 8 Nov 2026

L7 Chicago by LOTTE
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
203 N Wabash Ave Chicago IL
The price is £130 per night from 23 Nov to 24 Nov
£130
23 Nov - 24 Nov
includes taxes & fees
9/10 Wonderful! (1,557 reviews)
"We arrived and pulled up to valet parking. The attendant noted that he would keep our car in front because the hotel was having issues with some reservation. We went to check in and there was a long line. Some people seemed to ba waiting for help while others were being checked in. When it was our ..."

Reviewed on 8 Nov 2026

Sports Illustrated Resorts Chicago
See all 4,434 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 £719. 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

A large illuminated sign with the letters "CHICA" and a circular design.
Photo by © Choose Chicago
Open 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.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture 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.