Theatre District Vacations from ￥253,699

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    Save up to ￥45,448 when you book a flight and hotel together*

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The Latest Theatre District Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥301,364, price is now ￥253,699 per person
￥253,699
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
My son and I really enjoyed our

Reviewed on Dec 20, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was ￥405,962, price is now ￥330,854 per person
￥330,854
per person
Mar 2 - Mar 6
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Room was spotless and amazing. It was so luxurious and took a bath in the tub with the TV. Appreciated the upgrade and Service. The tea and breakfast were also lovely. It was an amazing stay for Christmas festivities in Chicago. It’s the best hotel!

Reviewed on Dec 19, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Price was ￥327,024, price is now ￥280,592 per person
￥280,592
per person
Feb 19 - Feb 25
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,404 reviews)
Staff was wonderful.

Reviewed on Dec 11, 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was ￥300,905, price is now ￥259,416 per person
￥259,416
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,000 reviews)
It’s amazing historical property

Reviewed on Dec 15, 2025

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
Downtown Chicago
Price was ￥299,992, price is now ￥265,560 per person
￥265,560
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (1,761 reviews)
This is a wonderful property. It is clean and modern and has a friendly and accommodating staff.

Reviewed on Dec 19, 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

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 ￥19,777 per night from Dec 26 to Dec 27
￥19,777
￥27,106 total
Dec 26 - Dec 27
includes taxes & fees
8.4/10 Very Good! (2,145 reviews)
Easy check in & out. Nice clean room, pool, & hotel. Hotel is old but that lends to a bit of nostalgia as maintenance & upkeep have keep the feeling of freshness alive.

Reviewed on Dec 19, 2025

Palmer House a Hilton Hotel
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥12,588 per night from Dec 30 to Dec 31
￥12,588
￥19,526 total
Dec 30 - Dec 31
includes taxes & fees
9.2/10 Wonderful! (2,139 reviews)
Clean, comfortable, convenient.

Reviewed on Dec 19, 2025

Silversmith Hotel Chicago Downtown
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 ￥24,896 per night from Jan 1 to Jan 2
￥24,896
￥35,620 total
Jan 1 - Jan 2, 2026
includes taxes & fees
9.2/10 Wonderful! (1,157 reviews)
Excellent location to stay in the heart of the city.

Reviewed on Dec 17, 2025

Pendry Chicago
See all 4,720 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 ￥253,699. 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

4.5/5(1,193 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
Ceiling of the Cadillac palace ...great place to see a show.

Cadillac Palace Theatre

4/5(1 review)

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

4.5/5(7 reviews)

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 acclaimed art scene in this vibrant area.

Chicago City Hall

Things to do

River tour boat in Chicago

Architecture River Tour

￥6,839
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥6,310
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,827
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel 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.