Theatre District Holidays

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Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was €1,073, price is now €940 per person
€940
per person
29 Dec - 2 Jan
found 14 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
18/10 Exceptional! (2,204 reviews)
The room was clean, staff was very friendly. Coffee available. Overall very happy with our stay

Reviewed on 9 Nov 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €1,274, price is now €1,045 per person
€1,045
per person
29 Dec - 2 Jan
found 14 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
18.8/10 Exceptional! (1,128 reviews)
Staff was our favorite part! Very very professional and friendly

Reviewed on 14 Nov 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was €1,225, price is now €1,055 per person
€1,055
per person
29 Dec - 2 Jan
found 14 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
18.8/10 Exceptional! (3,388 reviews)
Clean room, GREAT location, nice rooftop space. Nice bath products.

Reviewed on 13 Nov 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was €1,192, price is now €1,030 per person
€1,030
per person
29 Dec - 2 Jan
found 14 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
18/10 Exceptional! (1,000 reviews)
Everything was perfect

Reviewed on 12 Nov 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was €1,137, price is now €1,010 per person
€1,010
per person
29 Dec - 2 Jan
found 14 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Great stay as always- beautiful property, rooms, Game Room is a gem, and excellent staff; just a couple notes: Bring back The Milk Room! The lobby seating was less inviting with so much turned over to assigned-seating dining. Can the hotel offer at least complimentary coffee/tea for guests? I prepaid for breakfast but still had to pay $5 per cup of coffee.

Reviewed on 9 Nov 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 which includes a city

Downtown Chicago

4 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

Top hotels in Theatre District

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 €128 per night from 24 Nov to 25 Nov
€128
24 Nov - 25 Nov
includes taxes & fees
8.4/10 Very Good! (2,054 reviews)
The main lobby and bar area was beautifully decorated and a lovey area to relax and meet people

Reviewed on 11 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 €115 per night from 19 Nov to 20 Nov
€115
19 Nov - 20 Nov
includes taxes & fees
9.2/10 Wonderful! (4,024 reviews)
great hotel

Reviewed on 13 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 €126 per night from 14 Dec to 15 Dec
€126
14 Dec - 15 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 4,649 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 €940. 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.

Popular places to visit

Daley Plaza

Daley Plaza

You can learn about the history of Chicago when you stop by Daley Plaza. Experience the fascinating museums and entertainment choices in this vibrant area.

Daley Plaza
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

Things to do

Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

€38
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
River tour boat in Chicago

Architecture River Tour

€42
per adult
96% of travellers recommend
Architecture River Tour
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

€21
per adult
84% 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.