Theatre District Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to ฿27,000 when you book a flight and hotel together*

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

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Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Jul 2 - Jul 5

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.2/10 - Very good (2,733 reviews)
    "Peaceful!!!"
    Reviewed May 26, 2026
    Return • Los Angeles (LAX) - Chicago (ORD)
    LAX - ORD • Direct ORD - LAX • Direct
    ฿30,557
    ฿23,776
    per traveller
    found 22 hours ago
    Hotel Felix River North/Magnificent Mile
  • Front of property
    Jul 2 - Jul 5

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (4,260 reviews)
    "Breakfast included & location were really the selling points for me. The staff were super helpful and polite."
    Reviewed May 27, 2026
    Return • Los Angeles (LAX) - Chicago (ORD)
    LAX - ORD • Direct ORD - LAX • Direct
    ฿39,884
    ฿28,807
    per traveller
    found 22 hours ago
    Hotel Riu Plaza Chicago
  • Indoor wedding
    Jul 2 - Jul 5

    Swissotel - Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.0/10 - Wonderful (3,349 reviews)
    "It was a nice room. Only complaint would be air conditioning. I don’t do hot. Hate sweating. Had turned to 65 and still not really cold. Otherwise overall nice."
    Reviewed May 26, 2026
    Return • Los Angeles (LAX) - Chicago (ORD)
    LAX - ORD • Direct ORD - LAX • Direct
    ฿32,834
    ฿25,119
    per traveller
    found 22 hours ago
    Swissotel - Chicago
  • Breakfast, lunch, dinner and brunch served
    Jul 2 - Jul 5

    The Royal Sonesta Chicago River North + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (2,607 reviews)
    "The hotel was very nice. The room and room service were very good with a nice normal shower that did not spray water everywhere! We had breakfast one day at the hotel restaurant and it was delicious! Coffee in the lobby every morning was perfect and ice waters the rest of the day. The issue was the hotel restaurant closed after lunch and was closed for the night on both Sunday and Monday of Memorial Day Weekend when the hotel was packed with guests. There was no bar on the property open at..."
    Reviewed May 26, 2026
    Return • Los Angeles (LAX) - Chicago (ORD)
    LAX - ORD • Direct ORD - LAX • Direct
    ฿32,450
    ฿25,565
    per traveller
    found 22 hours ago
    The Royal Sonesta Chicago River North
  • Executive lounge
    Jul 2 - Jul 5

    Fairmont Chicago at Millennium Park + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    8.8/10 - Excellent (2,156 reviews)
    "Amazing view and clean room"
    Reviewed May 25, 2026
    Return • Los Angeles (LAX) - Chicago (ORD)
    LAX - ORD • Direct ORD - LAX • Direct
    ฿31,985
    ฿25,320
    per traveller
    found 22 hours ago
    Fairmont Chicago at Millennium Park

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

Central Loop Hotel

Central Loop Hotel

4 out of 5
111 West Adams Street Chicago IL
The price is ฿7,811 per night from 14 Jun to 15 Jun
฿7,811
฿9,287 total
14 Jun - 15 Jun
includes taxes & fees
8.6/10 Excellent! (2,168 reviews)
"Nice place and walking distance to the train station"

Reviewed on 26 May 2026

Central Loop Hotel
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 ฿6,929 per night from 14 Jun to 15 Jun
฿6,929
฿9,284 total
14 Jun - 15 Jun
includes taxes & fees
9/10 Wonderful! (2,554 reviews)
"I was very late arriving because my train was 8 hours late, and the staff couldn't have been more helpful! The room was very clean and comfortable and all of that was really appreciated. I would definitely recommend this hotel to anyone staying in Chicago."

Reviewed on 26 May 2026

The Allegro Royal Sonesta Hotel Chicago Loop
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
The price is ฿5,964 per night from 14 Jun to 15 Jun
฿5,964
฿7,090 total
14 Jun - 15 Jun
includes taxes & fees
8.8/10 Excellent! (3,521 reviews)
"Excellent option to stay. Very good location close to bus stations and tourist places. Thanks to Ms. Adriane who made everything more enjoyable during my stay."

Reviewed on 26 May 2026

Club Quarters Hotel, Central Loop, Chicago
See all 4,621 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 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
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

฿874
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

฿1,424
per adult
94% of travellers recommend
Skydeck - Willis Tower Admission
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

฿3,569
per adult
90% of travellers recommend
Chicago C3® by CityPASS®
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.