Theatre District Vacations from NT$39,077

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The Latest Theatre District Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was NT$50,065, price is now NT$39,077 per person
NT$39,077
per person
Apr 1 - Apr 8
found 1 day ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
I liked the hotel. The staff was very courteous and friendly. The room was cute. The location is fantastic.

Reviewed on 2026/1/20

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was NT$70,964, price is now NT$46,073 per person
NT$46,073
per person
Apr 1 - Apr 8
found 1 day ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Our stay at the RIU exceeded our expectations within the hotel! Only downside was that it didn’t have a parking garage. Although the parking across the street wasn’t bad at all.

Reviewed on 2026/1/20

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was NT$66,439, price is now NT$48,724 per person
NT$48,724
per person
Apr 1 - Apr 8
found 1 day ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Clean room and amenities

Reviewed on 2026/1/8

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was NT$64,196, price is now NT$47,727 per person
NT$47,727
per person
Apr 1 - Apr 8
found 1 day ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Room was extremely clean, and staff was very accommodating

Reviewed on 2026/1/17

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was NT$66,124, price is now NT$51,354 per person
NT$51,354
per person
Apr 1 - Apr 8
found 1 day ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Hotel was very clean. Concierge was great with advice. Sports bar pepperoni pizza was great and the french fries were just as freshly cooked. Room was clean. Bed was great. Shower pressure great. Toilet correct height for a man of my age. Pillows…..pillows with a firmness of that of a 48 year old mother who breast fed all her 7 children until 9 months old. Glad the kids are good but those pillows need work Hilton. God Bless and safe travels to all. See you next time.

Reviewed on 2026/1/20

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

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 NT$5,366 per night from Feb 5 to Feb 6
NT$5,366
NT$7,597 total
Feb 5 - Feb 6
includes taxes & fees
9.2/10 Wonderful! (1,142 reviews)
N/A

Reviewed on 2026/1/12

Pendry Chicago
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 NT$4,245 per night from Jan 27 to Jan 28
NT$4,245
NT$5,773 total
Jan 27 - Jan 28
includes taxes & fees
8.4/10 Very Good! (2,246 reviews)
Clean, attractive classic looking room and bathroom.

Reviewed on 2026/1/13

Palmer House a Hilton 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 NT$4,449 per night from Feb 3 to Feb 4
NT$4,449
NT$5,223 total
Feb 3 - Feb 4
includes taxes & fees
9.6/10 Exceptional! (3,567 reviews)
The room was very nice, mostly clean and an excellent location. The room design is great for people watching and enjoying the hustle and bustle of downtown.

Reviewed on 2026/1/19

L7 Chicago by LOTTE
See all 4,738 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 NT$39,077. 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 entertainment choices 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 acclaimed theater scene in this vibrant area.

Chicago City Hall
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.