Theatre District Vacations from ￥308,218

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The Latest Theatre District Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Oct 17 - Oct 24
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
The hotel is beautiful inside and out and the staff are super nice and helpful. Hotel is in a very crowded area. It can take time to get in and out with your car. A lot of noise from the outside even when staying on top floors. Hotel could be managed better. Elevator was broken for a whole day. Room had some minor repairs that were not done when we checked in.

Reviewed on Jul 28, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Oct 10 - Oct 17
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
I liked the hotel room's kitchen and it is very nice, however VERY small. The pool/amenities are also very nice. One major challenge was there was a last minute change to the location of our reservation from old town to fulton market. They did communicate the change and provided a discount, however, this occurred the day before our trip. The check-in process was also very disorganized and confusing. Information easily accessible in the reservation was not used, requiring extra check-in time. They told us a crib was available, and later found only a pack and play. I requested bedding for the pull out 4 times before someone brought them. Overall, management needs to improve their operations.

Reviewed on Jul 21, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 10 - Oct 17
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on Jul 26, 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
per person
Oct 17 - Oct 24
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Very nice location super friendly staff very modern and clear hotel

Reviewed on Jul 27, 2025

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
per person
Oct 10 - Oct 17
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,042 reviews)
Beautiful Hotel! Rooftop pool is wonderful!

Reviewed on Jul 27, 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 showing 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

Theatre District Hotel Deals

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 ￥23,097 per night from Aug 26 to Aug 27
￥23,097
￥27,112 total
Aug 26 - Aug 27
includes taxes & fees
9.2/10 Wonderful! (3,470 reviews)
"Great room and hotel. Loved the lobby and the terrace. The iPad in the room was pretty cool and the bed was comfortable. No complaints with the bathroom. I wish there was an ice machine, I had to get ice from the bar in the lobby. It would be nice to have some discounted parking, but I was able to ..."

Reviewed on Jul 28, 2025

citizenM Chicago Downtown
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 ￥25,609 per night from Aug 21 to Aug 22
￥25,609
￥33,755 total
Aug 21 - Aug 22
includes taxes & fees
8.2/10 Very Good! (1,810 reviews)
"Beautiful old hotel. Tremendous nostalgia"

Reviewed on Jul 27, 2025

Palmer House a Hilton Hotel
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 ￥23,150 per night from Aug 17 to Aug 18
￥23,150
￥31,902 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (1,905 reviews)
"Had a great stay."

Reviewed on Jul 27, 2025

The Allegro Royal Sonesta Hotel Chicago Loop
See all 4,581 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 vacation package cost?
We make it simple to travel the world, with Theatre District packages starting from as little as ￥308,218. You'll have the flexibility to bundle your favorite 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 vacation?
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 traveling 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 cozy apartment in the city, Expedia will help make it happen.
Can I choose my airline with a Theatre District Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines throughout the world. Our vacation 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 vacation 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 vacation 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.

Discover the most popular places to visit in Theatre District

Chicago Theatre showing signage

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
Ceiling of the Cadillac palace ...great place to see a show.

Cadillac Palace Theatre

You can get tickets for a performance at Cadillac Palace Theatre during your stay in Chicago. Discover the acclaimed theater scene and notable monuments in this vibrant area.

Cadillac Palace Theatre
Chicago City Hall

Chicago City Hall

Chicago City Hall is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or experience the entertainment choices in this vibrant area.

Chicago City Hall

Things to do

Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

￥6,157
per adult
86% of travellers recommend
Chicago: Architecture Boat Tour with Drinks
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,600
per adult
86% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago: Griffin Museum of Science and Industry Ticket

Chicago: Griffin Museum of Science and Industry Ticket

￥3,804
per adult
Chicago: Griffin Museum of Science and Industry Ticket
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.