Title: Book the Best Theatre District LUXURY Hotels - Upscale Hotels in Theatre District, Chicago | Expedia.ca [Theatre District Travel Guide](https://expedia.ca/Chicago-Theatre-District.dx651190586167894016)[Vacation Rentals in Chicago](https://expedia.ca/Chicago-Vacation-Rentals.d178248.Travel-Guide-VacationRentals)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Theatre District Car Rentals](https://expedia.ca/Car-Rentals-In-Theatre-District.d651190586167894016.Car-Rental-Guide)[Theatre District Vacations](https://expedia.ca/Theatre-District.d651190586167894016.Destination-Travel-Guides) ![Iconic signage in Chicago. It's best to go when it's all lit up for the best shots. It was quite a rainy night in Chicago when I tried to take this shot.](https://images.trvl-media.com/place/829/c8d056d1-097c-4c48-9109-18fb83db02d4.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Mattyboy876 # Find Luxury Hotels in Theatre District, Chicago - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Theatre District Luxury Hotels Tonight [Dec 29 - Dec 30](https://www.expedia.ca/Hotel-Search?regionId=651190586167894016&startDate=2025-12-29&endDate=2025-12-30&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Dec 30 - Dec 31](https://www.expedia.ca/Hotel-Search?regionId=651190586167894016&startDate=2025-12-30&endDate=2025-12-31&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=651190586167894016&startDate=2026-01-02&endDate=2026-01-04&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=651190586167894016&startDate=2026-01-09&endDate=2026-01-11&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top Theatre District Hotel Reviews ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Spotless room, very nice staff" [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 10/10 Excellent " Check in staff were great and room was clean. Worst part was house cleaner knocking at door at 1030am, after being up till 2am night before have a good time at football game. Hot tub amazing and our view!" [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg) ### Pendry Chicago 10/10 Excellent "A very clean room, everything smells good and fresh, very nice staff, the staff helps all the time, my family and I feels very secure in the hotel." [](https://expedia.ca/Chicago-Hotels-Pendry-Chicago.h982552.Hotel-Information) ![Central Loop Hotel](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/43ee742c_y.jpg) ### Central Loop Hotel 10/10 Excellent "Yeah " [](https://expedia.ca/Chicago-Hotels-Central-Loop-Hotel.h2151878.Hotel-Information) ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg) ### Palmer House a Hilton Hotel 10/10 Excellent "Great place " [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Hyatt Centric The Loop Chicago](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/af0ef9e5_y.jpg) ### Hyatt Centric The Loop Chicago 10/10 Excellent "Courteous welcoming clean and good restaurant " [](https://expedia.ca/Chicago-Hotels-Hyatt-Centric-The-Loop-Chicago.h9069667.Hotel-Information) ![L7 Chicago by LOTTE](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/6dfbfa42_y.jpg) ### L7 Chicago by LOTTE 10/10 Excellent "Room is clean and staffs are nice and helpful. Enjoyed my stay here and will be back again !" [](https://expedia.ca/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.Hotel-Information) ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg) ### theWit Chicago, a Hilton Hotel 10/10 Excellent "Stayed for a Broadway show. Beautiful hotel with a nice attached restaurant" [](https://expedia.ca/Chicago-Hotels-TheWit-Chicago-A-DoubleTree-By-Hilton-Hotel.h2463437.Hotel-Information) ![Club Quarters Hotel Wacker at Michigan, Chicago](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d_y.jpg) ### Club Quarters Hotel Wacker at Michigan, Chicago 10/10 Excellent "Clean room...friendly staff" [](https://expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h889753.Hotel-Information) ## Frequently asked questions ### Are you searching for a great accommodation for your luxury trip to Theatre District? ### What's the best luxury hotel in Theatre District? ### How many luxury hotels can I expect to find in Theatre District? ### What's there to see and do in Theatre District? ### How can I get around Theatre District? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in Chicago ](https://www.expedia.ca/4Star-Chicago-Hotels.s40-0-d178248.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Chicago ](https://www.expedia.ca/5Star-Chicago-Hotels.s50-0-d178248.Travel-Guide-Filter-Hotels) - [Hotels near Art Institute of Chicago ](https://www.expedia.ca/Art-Institute-Of-Chicago-Hotels.0-l6064021-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Chicago ](https://www.expedia.ca/Chicago-Apart-Hotels.d178248-aaApartHotels.Travel-Guide-Accommodation) - [Apartments in Chicago ](https://www.expedia.ca/Chicago-Apartments.d178248-aaApartments.Travel-Guide-Accommodation) - [B&B in Chicago ](https://www.expedia.ca/Chicago-Bed-And-Breakfast.d178248-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Condo Rentals in Chicago ](https://www.expedia.ca/Chicago-Condos.d178248-aaCondos.Travel-Guide-Accommodation) - [Cottages in Chicago ](https://www.expedia.ca/Chicago-Cottages.d178248-aaCottages.Travel-Guide-Accommodation) - [Hostels in Chicago ](https://www.expedia.ca/Chicago-Hostels.d178248-aaHostels.Travel-Guide-Accommodation) - [Adults Only Resorts & in Chicago ](https://www.expedia.ca/Chicago-Hotels-Adults-Only-Resorts.0-0-d178248-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Chicago ](https://www.expedia.ca/Chicago-Hotels-All-Inclusive-Hotel.0-0-d178248-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Beach-Hotel.0-0-d178248-tBeachHotel.Travel-Guide-Filter-Hotels) - [Best Western Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Best-Western.0-0-d178248--bBestWestern.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Boutique-Hotel.0-0-d178248-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Business-Hotel.0-0-d178248-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Casino-Hotel.0-0-d178248-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Cheap-Hotels.0-0-d178248-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Chicago ](https://www.expedia.ca/Chicago-Hotels-Couples-Resorts-Hotels.0-0-d178248-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Fairmont Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Fairmont.0-0-d178248--bFairmont.Travel-Guide-Filter-Hotels) - [Family Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Family-Hotel.0-0-d178248-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Golf-Hotel.0-0-d178248-tGolfHotel.Travel-Guide-Filter-Hotels) - [Green Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Green-Sustainable.0-0-d178248-tGreenSustainable.Travel-Guide-Filter-Hotels) - [Hilton Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Hilton-Hotels.0-0-d178248--bHiltonHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Historic-Hotel.0-0-d178248-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Chicago ](https://www.expedia.ca/Chicago-Hotels-Honeymoon-Hotels.0-0-d178248-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Chicago ](https://www.expedia.ca/Chicago-Hotels-Hotel-With-Early-Check-In.0-0-d178248-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Chicago ](https://www.expedia.ca/Chicago-Hotels-Hotel-With-Pool.0-0-d178248-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Chicago ](https://www.expedia.ca/Chicago-Hotels-Hotels-With-A-Lazy-River.0-0-d178248-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Chicago ](https://www.expedia.ca/Chicago-Hotels-Hotels-With-Balconies.0-0-d178248-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Chicago ](https://www.expedia.ca/Chicago-Hotels-Hotels-With-Bar.0-0-d178248-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Hotels with Childcare in Chicago ](https://www.expedia.ca/Chicago-Hotels-Hotels-With-Childcare.0-0-d178248-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - [Hotels with Free Airport Shuttle in Chicago ](https://www.expedia.ca/Chicago-Hotels-Hotels-With-Free-Airport-Shuttle.0-0-d178248-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Chicago ](https://www.expedia.ca/Chicago-Hotels-Hotels-With-Free-Breakfast.0-0-d178248-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Chicago ](https://www.expedia.ca/Chicago-Hotels-Hotels-With-Free-Parking.0-0-d178248-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Chicago ](https://www.expedia.ca/Chicago-Hotels-Hotels-With-Hot-Tubs.0-0-d178248-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Chicago ](https://www.expedia.ca/Chicago-Hotels-Hotels-With-Indoor-Pool.0-0-d178248-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Hotels with Kitchenettes in Chicago ](https://www.expedia.ca/Chicago-Hotels-Hotels-With-Kitchenettes.0-0-d178248-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in Chicago ](https://www.expedia.ca/Chicago-Hotels-Hotels-With-Smoking-Rooms.0-0-d178248-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [Hotels with Tennis Courts in Chicago ](https://www.expedia.ca/Chicago-Hotels-Hotels-With-Tennis-Courts.0-0-d178248-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels) - [Hotels with Waterslides in Chicago ](https://www.expedia.ca/Chicago-Hotels-Hotels-With-Waterslides.0-0-d178248-tHotelswithWaterslides.Travel-Guide-Filter-Hotels) - [Iberostar Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Iberostar.0-0-d178248--bIberostar.Travel-Guide-Filter-Hotels) - [Kimpton Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Kimpton-Hotels.0-0-d178248--bKimptonHotels.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-LGBT-Friendly-Hotel.0-0-d178248-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Lake Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Lake-Hotels.0-0-d178248-tLakeHotels.Travel-Guide-Filter-Hotels) - [Loews Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Loews.0-0-d178248--bLoews.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Luxury-Hotel.0-0-d178248-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Marriott Hotels & Resorts in Chicago ](https://www.expedia.ca/Chicago-Hotels-Marriott-Hotels-Resorts.0-0-d178248--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels) - [Motel 6 Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Motel-6.0-0-d178248--bMotel6.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Mountain-Hotels.0-0-d178248-tMountainHotels.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Oceanfront-Hotels.0-0-d178248-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Pet-Friendly-Hotel.0-0-d178248-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Romantic-Hotel.0-0-d178248-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Shopping-Hotel.0-0-d178248-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Ski Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Ski-Hotel.0-0-d178248-tSkiHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Spa-Hotel.0-0-d178248-tSpaHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Waterpark-Hotels.0-0-d178248-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Wedding-Hotels.0-0-d178248-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Winery-Hotel.0-0-d178248-tWineryHotel.Travel-Guide-Filter-Hotels) - [Wyndham Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Wyndham-Hotels.0-0-d178248--bWyndhamHotels.Travel-Guide-Filter-Hotels) - [Chicago Hotels ](https://www.expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels) - [Motels in Chicago ](https://www.expedia.ca/Chicago-Motels.d178248-aaMotels.Travel-Guide-Accommodation) - [Resorts in Chicago ](https://www.expedia.ca/Chicago-Resort-Hotels.d178248-aaResortHotels.Travel-Guide-Accommodation) - [Hotels near Chicago Theatre ](https://www.expedia.ca/Chicago-Theatre-Hotels.0-l6064049-0.Travel-Guide-Filter-Hotels) - [Business Hotels in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Business-Hotel.0-n6350699-0-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Couples-Resorts-Hotels.0-n6350699-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Golf Hotels in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Golf-Hotel.0-n6350699-0-tGolfHotel.Travel-Guide-Filter-Hotels) - [Green Hotels in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Green-Sustainable.0-n6350699-0-tGreenSustainable.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Hotels-With-A-Lazy-River.0-n6350699-0-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Hotels with Childcare in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Hotels-With-Childcare.0-n6350699-0-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - [Hotels with Tennis Courts in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Hotels-With-Tennis-Courts.0-n6350699-0-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels) - [Hotels with Waterslides in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Hotels-With-Waterslides.0-n6350699-0-tHotelswithWaterslides.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Mountain-Hotels.0-n6350699-0-tMountainHotels.Travel-Guide-Filter-Hotels) - [Ski Hotels in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Ski-Hotel.0-n6350699-0-tSkiHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Waterpark-Hotels.0-n6350699-0-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Winery-Hotel.0-n6350699-0-tWineryHotel.Travel-Guide-Filter-Hotels) - [Downtown Chicago Hotels ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Magnificent Mile ](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Couples-Resorts-Hotels.0-n800025-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Magnificent Mile ](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Romantic-Hotel.0-n800025-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Magnificent Mile ](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Waterpark-Hotels.0-n800025-0-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in Magnificent Mile ](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Winery-Hotel.0-n800025-0-tWineryHotel.Travel-Guide-Filter-Hotels) - [Magnificent Mile Hotels ](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels.0-n800025-0.Travel-Guide-Filter-Hotels) - [Hotels near Millennium Park ](https://www.expedia.ca/Millennium-Park-Hotels.0-l6069201-0.Travel-Guide-Filter-Hotels) - [Hotels near State Street ](https://www.expedia.ca/State-Street-Hotels.0-l6175182-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Cheap-Hotels.0-n800024-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotel-With-Early-Check-In.0-n800024-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [The Loop Hotels ](https://www.expedia.ca/The-Loop-Chicago-Hotels.0-n800024-0.Travel-Guide-Filter-Hotels) - [Flights to Chicago ](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights) - [Flights from Chicago ](https://www.expedia.ca/lp/flights/178248/flights-from-chicago) - [Flights from Toronto (YYZ) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) - [Visit Downtown Chicago ](https://www.expedia.ca/Chicago-Downtown-Chicago.dx6350699) - [Visit The Loop ](https://www.expedia.ca/Chicago-The-Loop.dx800024) - [Chicago Vacations ](https://www.expedia.ca/Chicago.d178248.Destination-Travel-Guides) - [Visit Chicago ](https://www.expedia.ca/Chicago.dx178248) - [All inclusive Vacation Packages Chicago ](https://www.expedia.ca/lp/theme-vacations/all-inclusive-vacations/178248/Chicago) - [Budget Rental Cars in Chicago ](https://www.expedia.ca/Budget-Car-Rentals-In-Chicago.d178248-c39.Car-Rental-Guide-Suppliers) - [Car rentals near Chicago ](https://www.expedia.ca/Car-Rentals-In-Chicago.d178248.Car-Rental-Guide) - [Enterprise Rental Cars in Chicago ](https://www.expedia.ca/Enterprise-Car-Rentals-In-Chicago.d178248-c15.Car-Rental-Guide-Suppliers) - [Minivan Car Rentals in Chicago ](https://www.expedia.ca/Minivan-Car-Rentals-In-Chicago.d178248-tMinivan.Car-Rental-Guide-Class) - [Chicago Vacation Rentals ](https://www.expedia.ca/Chicago-Vacation-Rentals.d178248.Travel-Guide-VacationRentals) - [Things to do in Chicago ](https://www.expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities) - [Book Hotels in Theatre District on Expedia.com ](https://www.expedia.com/Theatre-District-Chicago-Hotels-Luxury-Hotel.0-n651190586167894016-0-tLuxuryHotel.Travel-Guide-Filter-Hotels)