Theatre District Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Betina Winsig Hansen

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Breakfast and dinner served
    Jul 18 - Jul 21

    Omni Chicago Hotel + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,792 reviews)
    "Booked a room - got a suite! Enjoyed the extra space. A separate living room for watching TV or working at a desk. Staff at the hotel was very helpful. Enjoyed the breakfast too."
    Reviewed June 3, 2026
    Roundtrip • Hamilton (YHM) - Chicago (ORD)
    YHM - ORD • 1 stop ORD - YHM • 1 stop
    CA $1,723
    CA $1,307
    per traveller
    found 1 day ago
    Omni Chicago Hotel
  • Terrace/patio
    Aug 11 - Aug 15

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

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (2,526 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
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • Nonstop ORD - YUL • Nonstop
    CA $1,852
    CA $1,331
    per traveller
    found 21 hours ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Full-size fridge, microwave, oven, stovetop
    Aug 7 - Aug 10

    Level Chicago – Old Town + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.0/10 - Wonderful (488 reviews)
    "Very clean and loved the location and amenities with the store on the first floor was fantastic"
    Reviewed June 3, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,876
    CA $1,378
    per traveller
    found 1 day ago
    Level Chicago – Old Town
  • Lounge
    Jul 23 - Jul 26

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,122 reviews)
    "I absolutely loved it! I little bit noisy but close to literally everything!"
    Reviewed June 2, 2026
    Roundtrip • Montreal (YUL) - Chicago (MDW)
    YUL - MDW • 1 stop MDW - YUL • 1 stop
    CA $2,295
    CA $1,689
    per traveller
    found 1 day ago
    Pendry Chicago
  • 2 restaurants; breakfast, lunch, and dinner served
    Aug 11 - Aug 15

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (3,730 reviews)
    "Great location, really de ent too s and comfy bed"
    Reviewed June 6, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • Nonstop ORD - YUL • Nonstop
    CA $1,809
    CA $1,363
    per traveller
    found 21 hours ago
    LondonHouse Chicago, Curio Collection by Hilton

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

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 CA $312 per night from Jul 2 to Jul 3
CA $312
CA $413 total
Jul 2 - Jul 3
includes taxes & fees
8.6/10 Excellent! (2,479 reviews)
"N/A"

Reviewed on Jun 6, 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 CA $416 per night from Jul 2 to Jul 3
CA $416
CA $495 total
Jul 2 - Jul 3
includes taxes & fees
9.6/10 Exceptional! (4,144 reviews)
"Staff is super friendly and hotel is very clean. We had a king room with a river view and wished we had stayed a little longer. Hotel is convenient to everything and totally walkable. Just remember sunscreen!"

Reviewed on Jun 5, 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 CA $251 per night from Jul 2 to Jul 3
CA $251
CA $340 total
Jul 2 - Jul 3
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 Jun 6, 2026

Arlo Chicago
See all 4,525 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 . 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

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
CIBC Theatre

CIBC Theatre

You can get tickets for a performance at CIBC Theatre on your trip to Chicago. Discover the acclaimed theater scene and notable monuments in this vibrant area.

CIBC Theatre
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

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

CA $69
per adult
94% of travellers recommend
Chicago By Night 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.