Theatre District Packages (Flight + Hotel)

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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 ฿3,725 per night from 30 Oct to 31 Oct
฿3,725
฿4,373 total
30 Oct - 31 Oct
includes taxes & fees
9.2/10 Wonderful! (3,996 reviews)
Love

Reviewed on 24 Oct 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 ฿4,154 per night from 25 Nov to 26 Nov
฿4,154
฿5,923 total
25 Nov - 26 Nov
includes taxes & fees
8.8/10 Excellent! (2,164 reviews)
Located in a convenient area. Staff were nice. Hotel was beautiful.

Reviewed on 21 Oct 2025

The Allegro Royal Sonesta Hotel Chicago Loop
Pendry Chicago

Pendry Chicago

4.5 out of 5
230 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ฿5,887 per night from 23 Nov to 24 Nov
฿5,887
฿8,255 total
23 Nov - 24 Nov
includes taxes & fees
9.2/10 Wonderful! (1,127 reviews)
Loved it!

Reviewed on 22 Oct 2025

Pendry Chicago
See all 4,547 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.

Frequently asked questions

How much does a Theatre District holiday package cost?
We make it simple to travel the world, with Theatre District packages starting from as little as . You'll have the flexibility to bundle your favourite hotels, airlines and car rental. For the ultimate getaway, why not add some activities and tours to your itinerary?
How do I get a cheap travel package to Theatre District?
One of the simplest ways to save dollars (and time) is to bundle your bookings with Expedia. Flights, hotels, rental cars and activities — we've got it all. Select a combination that best fits you and see your savings pile up. We know a package deal is never one-size-fits-all. That's why we offer more than 550 partner airlines and 1,000,000 hotel options across the globe, which lets you customize your Theatre District getaway.
Where should I stay in Theatre District?
Urban adventurers come from all over the world to see McCormick Place and Millennium Park in Theatre District. Book yourself a room within a stone's throw of these must-see attractions to make sightseeing easy.
What are the top hotels in Theatre District?
Hotel Julian and Kimpton Hotel Monaco Chicago, an IHG Hotel are among the most well-known hotels in Theatre District. Why not have a look at the amenities and facilities at each and then make a decision?
How far in advance should I book my Theatre District holiday?
Reserving your flight early with Expedia means one less thing to worry about. Many air carriers advertise prices up to 12 months in advance. This is often the cheapest time to book. If circumstances have left you booking late, great deals to Theatre District are still known to appear in the weeks leading up to departure.
What does an Expedia Theatre District travel package include?
That depends on what you're after. If you're travelling alone, you might decide to combine hotels and flights. Taking the whole family to Theatre District? A travel package that includes flights, hotels and rental cars might suit you better. Expedia gives you the flexibility to tailor your travel package.
What should I know before booking a Theatre District travel package?
When you book your flights, hotels and car rentals together, you'll nab great discounts. Whether you're planning an island getaway in a villa or prefer to stay in a cosy apartment in the city, Expedia will help make it happen.
Can I choose my airline with a Theatre District Expedia holiday package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines throughout the world. Our holiday packages give you the freedom to pick from available flights, hotels and activities that fit your needs.
If I'm not able to travel, can I cancel my Theatre District holiday package?
Yes, you can. We understand that things don't always go to plan, so we're happy to help if you need to make changes to your Theatre District holiday package. You may be able to cancel or amend your itinerary at no cost if you've booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Head to our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.

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
Chicago Board of Trade Building

Chicago Board of Trade Building

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.

Chicago Board of Trade Building

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

฿948
per adult
84% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

฿1,438
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Chicago Hop-On Hop-Off Big Bus Tour

Big Bus Chicago Hop-On Hop-Off Big Bus Tour

฿1,177
per adult
84% of travellers recommend
Big Bus Chicago Hop-On Hop-Off Big Bus 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.