Theatre District Holidays

Photo by Betina Winsig Hansen

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Price found within the past 48 hours. Click for updated prices.
  • Smart TV
    Jul 9 - Jul 13

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (493 reviews)
    "Fully equipmet"
    Reviewed June 2, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,502
    €1,126
    per traveller
    found 2 hours ago
    Level Chicago Fulton Market
  • Lounge
    Jul 22 - Jul 25

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,124 reviews)
    "Delightful staff and property, perfect for downtown adventures"
    Reviewed June 7, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €2,085
    €1,630
    per traveller
    found 16 hours ago
    Pendry Chicago
  • Terrace/patio
    Jul 22 - Jul 25

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,884 reviews)
    "We love the pool, cleanliness in the room .Friendly staff"
    Reviewed June 6, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €2,085
    €1,699
    per traveller
    found 16 hours ago
    Trump International Hotel & Tower Chicago
  • Terrace/patio
    Jul 22 - Jul 25

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (2,528 reviews)
    "Loved the location. Fitness room was a little disappointing because it’s small and the there are only 2 peloton bikes, but one was out of commission."
    Reviewed June 4, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,750
    €1,431
    per traveller
    found 16 hours ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Lobby
    Jul 22 - Jul 25

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.2/10 - Very good (2,768 reviews)
    "The staff was fantastic. Our plane arrived late, we were starving, didn’t know where to go or even have a plan, and the staff jumped right in and directed us to the perfect place: Portillo’s. They came up with lots of great suggestions that fit exactly what we wanted to do and where to eat. The rates were very reasonable, it’s situated in the middle of downtown, lots of restaurants on the same block, and plenty of Chicago nightlife. I would definitely stay there again."
    Reviewed June 7, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,475
    €1,217
    per traveller
    found 16 hours ago
    Hotel Felix River North/Magnificent Mile

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

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

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 €237 per night from 3 Jul to 4 Jul
€237
3 Jul - 4 Jul
includes taxes & fees
8.6/10 Excellent! (2,482 reviews)
"Parking can be charged to room"

Reviewed on 7 Jun 2026

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 €308 per night from 1 Jul to 2 Jul
€308
1 Jul - 2 Jul
includes taxes & fees
9.6/10 Exceptional! (4,148 reviews)
"The door man was very friendly and helpful"

Reviewed on 7 Jun 2026

L7 Chicago by LOTTE
Arlo Chicago

Arlo Chicago

4 out of 5
168 N Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is €194 per night from 6 Jul to 7 Jul
€194
6 Jul - 7 Jul
includes taxes & fees
9.4/10 Exceptional! (2,128 reviews)
"Staff was excellent rooms were excellent. The food is off the chain. The restaurant is phenomenal. Definitely a great place to stay in the heart of downtown Chicago."

Reviewed on 6 Jun 2026

Arlo Chicago
See all 4,586 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 . 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

Chicago Christkindl Holiday Market

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
Board of Trade

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

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€23
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

€36
per adult
94% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€37
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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.