A street lamp with a theater district sign, surrounded by tall buildings.

Theatre District Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • 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

The Latest Theatre District Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 19 - Dec 25

    The Emily Hotel + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    9.2/10 - Wonderful (1,360 reviews)
    "Great location in the West Loop. The rooms are big and the beds are comfy. We’ve stayed there three times. The outdoor theatre shows great films and has an outdoor bar. Coffee shop is in the lobby. There’s not really a fun bar, but lots of places to have cocktails in the neighborhood. A lobby fireplace would be a nice addition in the lobby for cold Chicago nights."
    Reviewed November 13, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,734
    CA $1,159
    per traveller
    found 1 day ago
    The Emily Hotel
  • Jan 22 - Jan 25

    The Peninsula Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,000 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $4,165
    CA $2,806
    per traveller
    found 0 hours ago
    The Peninsula Chicago
  • Dec 28 - Jan 2

    Park Hyatt Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (1,000 reviews)
    "This place was amazing and the hotel staff was extremely helpful"
    Reviewed November 10, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $3,057
    CA $2,112
    per traveller
    found 21 hours ago
    Park Hyatt Chicago
  • Jan 22 - Jan 25

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

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (2,763 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,821
    CA $1,272
    per traveller
    found 0 hours ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Dec 28 - Jan 2

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (2,076 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $3,161
    CA $2,208
    per traveller
    found 21 hours ago
    Trump International Hotel & Tower Chicago

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
Learn more about Theatre District

Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

Discover the most popular places to visit in Theatre District

What to do near Theatre District

Theatre District Hotel Deals

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 vacation package cost?

We make it simple to travel the world, with Theatre District packages starting from as little as CA $1,159. 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.