Theatre District Holidays from NZ$3,146

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Top Holiday Package Deals in Theatre District

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

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was NZ$4,303, price is now NZ$3,146 per person
NZ$3,146
per person
26 Dec - 2 Jan
found 18 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
The room had no soundproofing. Every night a car was revving loudly across Michigan Ave around midnight, making it impossible to sleep without noise-cancelling AirPods.

Reviewed on 18 Nov 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was NZ$6,133, price is now NZ$4,038 per person
NZ$4,038
per person
26 Dec - 2 Jan
found 17 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18/10 Exceptional! (380 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.

Reviewed on 9 Nov 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was NZ$5,140, price is now NZ$3,607 per person
NZ$3,607
per person
26 Dec - 2 Jan
found 18 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18.4/10 Exceptional! (1,264 reviews)
Perfect stay and location. Room was clean and just what we needed. It’s nothing special

Reviewed on 11 Nov 2025

Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
Downtown Chicago
Price was NZ$4,753, price is now NZ$3,402 per person
NZ$3,402
per person
26 Dec - 2 Jan
found 17 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18.4/10 Exceptional! (983 reviews)
Everything was good

Reviewed on 17 Nov 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was NZ$6,630, price is now NZ$4,802 per person
NZ$4,802
per person
26 Dec - 2 Jan
found 17 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
Political stigma aside, I must say, this property is stunning across the board. From the moment you enter the building you're met with this amazingly inviting fragrance. The Room was spotless. All the staff was sincere, kind, hospitable, and surprisingly diverse. Also, The front desk was exceptionally accommodating while I (minimally) "stress tested" the room service. 10/10 would and Will return. Mr. & Mrs.S

Reviewed on 17 Nov 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$264 per night from 24 Nov to 25 Nov
NZ$264
24 Nov - 25 Nov
includes taxes & fees
8.4/10 Very Good! (2,057 reviews)
Excellent!

Reviewed on 13 Nov 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$243 per night from 25 Nov to 26 Nov
NZ$243
25 Nov - 26 Nov
includes taxes & fees
9.2/10 Wonderful! (4,039 reviews)
Clean hotel, good location close to everything, friendly and helpful staff.

Reviewed on 17 Nov 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$258 per night from 18 Dec to 19 Dec
NZ$258
18 Dec - 19 Dec
includes taxes & fees
8.8/10 Excellent! (2,205 reviews)
Great hotel

Reviewed on 10 Nov 2025

The Allegro Royal Sonesta Hotel Chicago Loop
See all 4,650 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$3,146. 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 acclaimed theatre scene and fascinating museums in this vibrant area.

Chicago Board of Trade Building

Activities

Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

NZ$76
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

NZ$43
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Relax and enjoy the view

Chicago Architecture Center River Cruise aboard First Lady

NZ$97
per adult
96% of travellers recommend
Chicago Architecture Center River Cruise aboard First Lady
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.