Theatre District Holidays from NZ$11,381

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Top Holiday Package Deals in Theatre District

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
per person
30 Oct - 2 Nov
found 9 hours ago
Return flight included
Dunedin (DUD) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
Terrible mattresses, old and crunchy or something; bad lumpy pillows. No coffee or water in the room. If you want free coffee, you gotta track to the lobby during coffee hours and pay a "resort" fee for the experience.

Reviewed on 17 Aug. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
30 Oct - 2 Nov
found 9 hours ago
Return flight included
Dunedin (DUD) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
One of the best hotels. I will definitely stay here again.

Reviewed on 16 Aug. 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
30 Oct - 2 Nov
found 9 hours ago
Return flight included
Dunedin (DUD) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug. 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
30 Oct - 2 Nov
found 9 hours ago
Return flight included
Dunedin (DUD) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
This was property was centrally located next to everything that a first time visitor would like to experience. The access to the parks, museums, the Riverwalk and dining options makes for an enjoyable trip. The only downside was having to wait a considerable time for the elevators. Having 5 elevators and not all running at the same time, led to long wait times for a popular hotel with many guests.

Reviewed on 17 Aug. 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
30 Oct - 2 Nov
found 9 hours ago
Return flight included
Dunedin (DUD) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
The most beautiful hotel !

Reviewed on 17 Aug. 2025

Our guide on 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

Our pick of the best 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 NZ$386 per night from 2 Sept to 3 Sept
NZ$386
2 Sept - 3 Sept
includes taxes & fees
8.4/10 Very Good! (1,862 reviews)
"Beautiful hotel within walking distance to great restaurants, shopping and sites. We had a wonderful weekend"

Reviewed on 17 Aug. 2025

Palmer House a Hilton Hotel
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 NZ$285 per night from 24 Aug to 25 Aug
NZ$285
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (3,571 reviews)
"The hotel is on the 4th floor with limited signage in front. Parking is two blocks away at $50 a day. I arrived in the middle of a heavy rain storm. They handed me an umbrella for the walk back. Facility is immaculate and perfect if you are not driving."

Reviewed on 15 Aug. 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 NZ$406 per night from 24 Aug to 25 Aug
NZ$406
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (1,938 reviews)
Great Bar
"Great hotel and next to the theater we were going to, which was convenient. It was also easy to walk to other attractions. It felt very safe . And the bar was Great!! Honestly i would stay here again just for the bar! My bartender answered questions, gave delicious suggestions, and made a great drink! ..."

Reviewed on 13 Aug. 2025

The Allegro Royal Sonesta Hotel Chicago Loop
See all 4,591 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 NZ$11,381. 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.

Discover the most popular places to visit in Theatre District

Richard J. Daley Center

Richard J. Daley Center

Richard J. Daley Center 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 visit the notable monuments in this vibrant area.

Richard J. Daley Center
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 entertainment choices and acclaimed theatre scene in this vibrant area.

Chicago Board of Trade Building

Activities

Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

NZ$70
per adult
88% of travellers recommend
Chicago: Architecture Boat Tour with Drinks
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

NZ$41
per adult
86% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

NZ$177
per adult
86% of travellers recommend
Chicago C3® by CityPASS®
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.