Title: Theatre District Holidays 2026 from £741 | Expedia.co.uk [Theatre District Travel Guide](https://expedia.co.uk/Chicago-Theatre-District.dx651190586167894016)[Hotels in Theatre District](https://expedia.co.uk/Theatre-District-Chicago-Hotels.0-n651190586167894016-0.Travel-Guide-Filter-Hotels)[Flights to Chicago](https://expedia.co.uk/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.co.uk/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Theatre District Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Theatre-District.d651190586167894016.Car-Hire-Guide) ![](https://images.trvl-media.com/place/829/1a8abde0-c15d-4b25-9c4c-74d2678f7428.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Theatre District Holidays from £741 ## 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 £335 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 Packages with flights are ATOL protected ### Your Theatre District Holiday Leap into your next thrilling adventure with one of our Theatre District holiday packages. Spend your time getting to know this neighbourhood's countless charms, such as its culture. Hoping to do some sightseeing during your trip to Theatre District? Pencil in a visit to nearby attractions such as [Millennium Park](https://www.expedia.co.uk/Millennium-Park-Downtown-Chicago.d6069201.Attraction), [Willis Tower](https://www.expedia.co.uk/Willis-Tower-Downtown-Chicago.d6064069.Attraction) and [Art Institute of Chicago](https://www.expedia.co.uk/Art-Institute-Of-Chicago-Downtown-Chicago.d6064021.Attraction). Expedia can help you turn your ideal Theatre District holiday into reality, no matter your budget or travel plans. Price found within the past 48 hours. Click for updated prices. ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/28e8042f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago £741 per person 16 Apr - 19 Apr found 5 hours ago Return direct flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (1,137 reviews) Great location, clean and very nice restaurant and bar. Reviewed on 9 Mar 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago Save 100% on your flight £1,482 per person 26 May - 31 May found 21 hours ago Return direct flight included London (LGW) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Great spot and view, would stay again! Reviewed on 13 Mar 2026 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago Save 100% on your flight £1,717 per person 26 May - 31 May found 21 hours ago Return direct flight included London (LGW) to Chicago (ORD) 9.4/10 Exceptional! (1,844 reviews) Room was perfect/staff was great Reviewed on 12 Mar 2026 ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago £972 per person 1 Jun - 4 Jun found 5 hours ago Return direct flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) Staff was really nice and polite, Portuguese and Spanish speakers which was a must and breakfast buffet was amazing, highly recommended! Reviewed on 15 Mar 2026 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/e294b3a4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago Save 100% on your flight £2,176 per person 26 May - 31 May found 21 hours ago Return direct flight included London (LGW) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) We had everything we needed and more! Great location for shopping and viewing a the beautiful city of Chicago. Reviewed on 13 Mar 2026 ## 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](https://expedia.co.uk/Chicago-Theatre-District.dx651190586167894016) ![Downtown Chicago featuring a city](https://images.trvl-media.com/place/6350699/f8ae2db6-94cc-4898-aa46-e275588c3787.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### 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](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=6350699) ![Magnificent Mile - River North](https://images.trvl-media.com/place/800025/2f4bc1ac-f370-4b72-8a89-0aa7dcb93f0c.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Magnificent Mile Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes. [Find hotels in Magnificent Mile](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=800025) ![The Loop - Downtown featuring a river or creek](https://images.trvl-media.com/place/800024/9e323a45-98da-4519-b5ca-71275e70174f.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### The Loop 4.5/5(187 area reviews) Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean. [Find hotels in The Loop](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=800024) ![River North showing railway items, street scenes and a city](https://images.trvl-media.com/place/6350695/b009c703-f7ab-4e4c-95a4-4b883071adef.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### River North Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city. [Find hotels in River North](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=6350695) ![Chicago featuring a city and modern architecture](https://images.trvl-media.com/place/6059328/2fb61786-4c0f-40e8-ae4e-a0fad3f9539a.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Lincoln Park 5/5(5 area reviews) Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining. [Find hotels in Lincoln Park](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=6059328) ## Top hotels in Theatre District ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Palmer House a Hilton Hotel 17 E Monroe St Chicago IL Fully refundableReserve now, pay when you stay £138 5 Apr - 6 Apr includes taxes & fees 8.6/10 Excellent! (2,326 reviews) We had a great stay and the staff are very friendly and accommodating. Reviewed on 15 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=8079&PinnedHotelID=8079&HadPinnedHotel=true®ionId=651190586167894016) ![L7 Chicago by LOTTE](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/bb12c333_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### L7 Chicago by LOTTE 225 N Wabash Ave Chicago IL Fully refundableReserve now, pay when you stay £136 31 Mar - 1 Apr includes taxes & fees 9.6/10 Exceptional! (3,772 reviews) The room was clean and the staff was friendly Reviewed on 15 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=31%2F03%2F2026&endDate=01%2F04%2F2026&selected=4200&PinnedHotelID=4200&HadPinnedHotel=true®ionId=651190586167894016) ![Hyatt Centric The Loop Chicago](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/0ec157ec_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Centric The Loop Chicago 100 W. Monroe St Chicago IL Fully refundableReserve now, pay when you stay £141 20 Mar - 21 Mar includes taxes & fees 9/10 Wonderful! (2,404 reviews) Close to all the spots I wanted to see. Close to transit . Enjoyed my stay Reviewed on 12 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=20%2F03%2F2026&endDate=21%2F03%2F2026&selected=9069667&PinnedHotelID=9069667&HadPinnedHotel=true®ionId=651190586167894016) [See all 4,662 properties in Theatre District](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=16%2F03%2F2026&endDate=17%2F03%2F2026®ionId=651190586167894016) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holidays](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![Holiday in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ## Frequently asked questions ### How much does a Theatre District travel package cost? ### If I'm not able to travel, can I cancel my Theatre District travel package? ### How do I get a cheap travel package to Theatre District? ### Does Expedia offer Book Now, Pay Later Theatre District holidays? > - Pay monthly holidays: Klarna offers easy monthly payment plans that work for all types of budgets, so you can take that well-deserved holiday now. > - Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay off your holiday across multiple transactions. > - Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to hit that "book now" button, go for a low deposit holiday payment plan from Klarna. ### Where should I stay in Theatre District? ### What are the top hotels in Theatre District? ### How far in advance should I book my Theatre District holiday? ### What does an Expedia Theatre District travel package include? ### What should I know before booking a Theatre District travel package? ### Can I choose my airline with a Theatre District Expedia travel package? ### Popular places to visit ![Chicago Theatre showing signage](https://images.trvl-media.com/place/6064049/185f7905-1d94-4fcb-94f4-f8203317be58.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago Theatre 4/5(10 reviews) 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. [](https://expedia.co.uk/Chicago-Theatre-Downtown-Chicago.d6064049.Attraction) ![Chicago](https://images.trvl-media.com/place/829/9c89ff56-3bcc-456f-9697-f88bb9dbb92e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### CIBC Theatre You can enjoy a show at CIBC Theatre on your trip to Chicago. Discover the acclaimed art galleries and notable monuments in this vibrant area. [](https://expedia.co.uk/CIBC-Theatre-Downtown-Chicago.d553248621563220853.Attraction) ### Things to do ![360 CHICAGO Observation Deck ](https://mediaim.expedia.com/localexpert/170348/1cbf6a0b-f355-4f8a-a858-37fdc0668a64.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 360 CHICAGO Observation Deck £19 per adult **86%** of travellers recommend [](https://expedia.co.uk/things-to-do/360-chicago-observation-deck.a170348.activity-details) ![Skydeck - Willis Tower Admission ](https://mediaim.expedia.com/localexpert/1342523/52299998-0f25-4483-b147-6aa89e72ca8e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Skydeck - Willis Tower Admission £33 per adult **98%** of travellers recommend [](https://expedia.co.uk/things-to-do/skydeck-willis-tower-admission.a1342523.activity-details) ![Flyover in Chicago](https://mediaim.expedia.com/localexpert/50023979/095bdacd-a8be-4515-aac0-469239aa8c0a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Flyover in Chicago £28 per adult **98%** of travellers recommend [](https://expedia.co.uk/things-to-do/flyover-in-chicago.a50023979.activity-details) [See all activities in Chicago](https://expedia.co.uk/things-to-do/search?rid=651190586167894016) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.