Title: Cheap Flights to Chicago , IL from CA $155 - Expedia.ca ![City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Cheap Flights to Chicago , IL from CA $155 [View CA $155 flight on Tue, Jan 6, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YTZ,to:MDW,departure:06/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:154.60&airProductToken=AQo1CjMI0IgBEgQyMzg3GPjMASDssAEo19uBAzDF3IEDOE1AAFgBagVCQVNJQ3IITTJOMFpSWkwSCggBEAEYASoCUEQYASIECAEQASgCKAMoBDAB) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travellers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Leaving from Going to Departing Returning Add a place to stay Add a car Direct flights only [Chicago Travel Guide](https://expedia.ca/Chicago.dx178248)[Hotels in Chicago](https://expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Chicago Car Rentals](https://expedia.ca/Car-Rentals-In-Chicago.d178248.Car-Rental-Guide)[Chicago Vacation Packages](https://expedia.ca/Chicago.d178248.Destination-Travel-Guides) ## Popular airlines to Chicago - ![Delta](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Chicago, Illinois, United States of America,departure:28/11/2025TANYT&leg2=from:Chicago, Illinois, United States of America,to:CMH,departure:05/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Chicago, Illinois, United States of America,departure:28/11/2025TANYT&leg2=from:Chicago, Illinois, United States of America,to:CMH,departure:05/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![Frontier Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Chicago, Illinois, United States of America,departure:28/11/2025TANYT&leg2=from:Chicago, Illinois, United States of America,to:CMH,departure:05/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Chicago, Illinois, United States of America,departure:28/11/2025TANYT&leg2=from:Chicago, Illinois, United States of America,to:CMH,departure:05/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![Southwest Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Chicago, Illinois, United States of America,departure:28/11/2025TANYT&leg2=from:Chicago, Illinois, United States of America,to:CMH,departure:05/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![Spirit Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg) Spirit Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Chicago, Illinois, United States of America,departure:28/11/2025TANYT&leg2=from:Chicago, Illinois, United States of America,to:CMH,departure:05/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ![Alaska Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Chicago, Illinois, United States of America,departure:28/11/2025TANYT&leg2=from:Chicago, Illinois, United States of America,to:CMH,departure:05/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![notification illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* - ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 30% on select hotels after you book a flight\* - ![trophy illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.ca/login) ## How much is the cheapest flight to Chicago? Prices were available within the past 7 days and start at CA $155 for one-way flights and CA $248 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Wed, May 20 - Sat, May 23 YTZ Toronto MDW Chicago CA $248 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:MDW,departure:20/05/2026TANYT&leg2=from:MDW,to:YTZ,departure:23/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:248.00&airProductToken=AQokCiII0IgBEgQyMzkzGPjMASDssAEo18GNAzDEwo0DOE1AAFgBCiQKIgjQiAESBDIzODgY7LABIPjMASiQ4Y0DMPThjQM4TUAAWAESCggBEAEYASoCUEQYASIECAEQASgEMAE) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Mon, Feb 2 - Fri, Feb 6 YYZ Toronto ORD Chicago CA $258 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:02/02/2026TANYT&leg2=from:ORD,to:YYZ,departure:06/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:257.04&airProductToken=AQozCjEIwYYBEgM1MDkYmM4BIK4cKOKPhAMw2pCEAzhHQABYAWoFQkFTSUNyCEdOQTJBMkJBCjMKMQjBhgESAzUxMBiuHCCYzgEoh76EAzDqvoQDOEdAAFgBagVCQVNJQ3IIR05BMkEyQkESCggBEAEYASoCQUMYASIECAEQASgCKAMoBDAN) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sun, Feb 22 - Thu, Feb 26 YYZ Toronto ORD Chicago CA $258 Roundtrip found 1 hour ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:22/02/2026TANYT&leg2=from:ORD,to:YYZ,departure:26/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:257.04&airProductToken=AQojCiEI1YIBEgQzNjQwGJjOASCuHCj48YUDMPTyhQM4TkAAWAEKIwohCNWCARIEMzY3NBiuHCCYzgEo55qGAzDVm4YDOE5AAFgBEgoIARABGAEqAlVBGAEiBAgBEAEoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Mon, Feb 2 - Fri, Feb 6 YYZ Toronto ORD Chicago CA $264 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:02/02/2026TANYT&leg2=from:ORD,to:YYZ,departure:06/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:263.39&airProductToken=AQo0CjIIwYIBEgQzNjEwGJjOASCuHCiAkIQDMPiQhAM4QkAAWAFqBUJBU0lDcghPVkFDWlNCWApnCjEIwYIBEgQxODU0GK4cIO9ZKNq3hAMw0biEAzhCQABYAWoFQkFTSUNyCE9WQUNaU0JYCjIIwYIBEgQ1ODg1GO9ZIJjOASjBuoQDMK67hAM4QkABWAFqBUJBU0lDcghPVkFDWlNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![Air Transat](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/TS.gif) Thu, Apr 30 - Wed, May 6 YTZ Toronto MDW Chicago CA $290 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:MDW,departure:30/04/2026TANYT&leg2=from:MDW,to:YTZ,departure:06/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:289.98&airProductToken=AQo_Cj0I1KYBEgQ3MDYwGPjMASDssAEo292LAzDJ3osDOFFAAFgBagNCR1RyCFEyTjBaUlpMegoI0IgBEgQ3MDYwCj8KPQjUpgESBDczMTUY7LABIPjMASi8pYwDMKKmjAM4UUAAWAFqA0JHVHIIUTJOMFpSWkx6CgjQiAESBDczMTUSCggBEAEYASoCVFMYASIECAEQASgCKAMoBDAN) ## Find the cheapest month to fly from Columbus (CMH) to Chicago (CHI) ### August is typically the cheapest month to fly From CA $120 - CA $514 per traveller. Expedia.ca gives you the best tools to secure great deals on flights to Chicago. Use our easy and convenient booking engine to browse nonstop flights and convenient departure points every day of the year. Search airfares from the top airlines to book your perfect flight to Chicago. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Chicago. Using our booking engine is simple - just type in your points of travel and preferred dates and Expedia.ca does the rest! If your travel times are flexible, you can find even better bargains by adjusting your flight dates. Browse connecting flights to increase your chances of finding even lower fares. Thanks to Expedia's Best Price Guarantee, you can book your Chicago flights with full confidence knowing that you've found the best deal online. Expedia.ca makes the booking process easy and stress-free by offering support along the entire way. Our friendly staff is available 24 hours a day to provide assistance and help you book your ticket. Call us toll-free at 1-888-397-3342 to answer any questions that you may have about your trip to Chicago. Looking to save even more? Get additional savings by bundling your Chicago flight with a hotel and/or car rental to create a bargain travel package. Early birds can discover terrific savings by booking in advance while last minute travelers can enjoy great last minute deals. With Expedia.ca, there's no shortage of options to save even more on your Chicago trip! Flights to Chicago information | Destination airport | O'Hare Intl. | | --- | --- | | Destination airport IATA code | ORD | | Destination city name | Chicago | | Roundtrip price | CA $107 | ## Need more than a Flight to Chicago? Heading to Chicago? Explore Chicago with Expedia's Travel Guides to find the best hotels, vacation packages, car rental deals and more! [Chicago Hotels](https://expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels)[Chicago Vacation Rentals](https://expedia.ca/Chicago-Vacation-Rentals.d178248.Travel-Guide-VacationRentals)[Chicago Car Rentals](https://expedia.ca/Car-Rentals-In-Chicago.d178248.Car-Rental-Guide)[Chicago Vacations](https://expedia.ca/Chicago.d178248.Destination-Travel-Guides)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities) ## Trending flights to Chicago Prices were available within the past 7 days and start at CA $155 for one-way flights and CA $248 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Wed, May 20 - Sat, May 23 YTZ Toronto MDW Chicago CA $248 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:MDW,departure:20/05/2026TANYT&leg2=from:MDW,to:YTZ,departure:23/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:248.00&airProductToken=AQokCiII0IgBEgQyMzkzGPjMASDssAEo18GNAzDEwo0DOE1AAFgBCiQKIgjQiAESBDIzODgY7LABIPjMASiQ4Y0DMPThjQM4TUAAWAESCggBEAEYASoCUEQYASIECAEQASgEMAE) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars ### Lodging - [3 Star Hotels in The Loop](https://www.expedia.ca/3Star-The-Loop-Chicago-Hotels.s30-n800024-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in The Loop](https://www.expedia.ca/4Star-The-Loop-Chicago-Hotels.s40-n800024-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in The Loop](https://www.expedia.ca/5Star-The-Loop-Chicago-Hotels.s50-n800024-0.Travel-Guide-Filter-Hotels) - [Hotels near Adams-Wabash Station](https://www.expedia.ca/Adams-Wabash-Station-Hotels.d6210258.Travel-Guide-Hotels) - [Houseboats in Adams-Wabash Station](https://www.expedia.ca/Adams-Wabash-Station-Houseboats.d6210258-aaHouseboats.Travel-Guide-Accommodation) - [Hotels near Art Institute of Chicago](https://www.expedia.ca/Art-Institute-Of-Chicago-Hotels.0-l6064021-0.Travel-Guide-Filter-Hotels) - [Hotels near CIBC Theatre](https://www.expedia.ca/CIBC-Theatre-Hotels.0-l553248621563220853-0.Travel-Guide-Filter-Hotels) - [Hotels near Chagall's Four Seasons](https://www.expedia.ca/Chagalls-Four-Seasons-Hotels.0-l553248621533116569-0.Travel-Guide-Filter-Hotels) - [Hotels near Chase Tower](https://www.expedia.ca/Chase-Tower-Hotels.0-l553248621555594882-0.Travel-Guide-Filter-Hotels) - [Hotels near Chicago Temple](https://www.expedia.ca/Chicago-Temple-Hotels.0-l553248621561883126-0.Travel-Guide-Filter-Hotels) - [Hotels near Chicago Theatre](https://www.expedia.ca/Chicago-Theatre-Hotels.0-l6064049-0.Travel-Guide-Filter-Hotels) - [Downtown Chicago Hotels](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Madison-Wabash Station](https://www.expedia.ca/Madison-Wabash-Station-Apart-Hotels.d6210251-aaApartHotels.Travel-Guide-Accommodation) - [Hotels near Madison-Wabash Station](https://www.expedia.ca/Madison-Wabash-Station-Hotels.d6210251.Travel-Guide-Hotels) - [Inns in Madison-Wabash Station](https://www.expedia.ca/Madison-Wabash-Station-Inns.d6210251-aaInns.Travel-Guide-Accommodation) - [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 Monroe Station](https://www.expedia.ca/Monroe-Station-Hotels.d6189309.Travel-Guide-Hotels) - [Houseboats in Monroe Station](https://www.expedia.ca/Monroe-Station-Houseboats.d6210064-aaHouseboats.Travel-Guide-Accommodation) - [Hotels near Richard J. Daley Center](https://www.expedia.ca/Richard-J-Daley-Center-Hotels.0-l6175173-0.Travel-Guide-Filter-Hotels) - [Hotels near State Street](https://www.expedia.ca/State-Street-Hotels.0-l6175182-0.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Adults-Only-Resorts.0-n800024-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Beach-Hotel.0-n800024-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Best Western Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Best-Western.0-n800024-0--bBestWestern.Travel-Guide-Filter-Hotels) - [Boutique Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Boutique-Hotel.0-n800024-0-tBoutiqueHotel.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) - [Destination Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Destination-Hotels.0-n800024-0--bDestinationHotels.Travel-Guide-Filter-Hotels) - [Fairmont Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Fairmont.0-n800024-0--bFairmont.Travel-Guide-Filter-Hotels) - [Family Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Family-Hotel.0-n800024-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Golf-Hotel.0-n800024-0-tGolfHotel.Travel-Guide-Filter-Hotels) - [Hilton Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hilton-Hotels.0-n800024-0--bHiltonHotels.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Honeymoon-Hotels.0-n800024-0-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotel-With-Pool.0-n800024-0-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Free Airport Shuttle in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Free-Airport-Shuttle.0-n800024-0-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Free-Breakfast.0-n800024-0-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Free-Parking.0-n800024-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Hot-Tubs.0-n800024-0-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Indoor-Pool.0-n800024-0-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Hotels with Tennis Courts in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Tennis-Courts.0-n800024-0-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels) - [Kimpton Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Kimpton-Hotels.0-n800024-0--bKimptonHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Luxury-Hotel.0-n800024-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Marriott Hotels & Resorts in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Marriott-Hotels-Resorts.0-n800024-0--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Oceanfront-Hotels.0-n800024-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Romantic Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Romantic-Hotel.0-n800024-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Shopping Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Shopping-Hotel.0-n800024-0-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Spa-Hotel.0-n800024-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [The Loop Hotels](https://www.expedia.ca/The-Loop-Chicago-Hotels.0-n800024-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Theatre District](https://www.expedia.ca/Theatre-District-Chicago-Hotels-Cheap-Hotels.0-n651190586167894016-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Theatre District](https://www.expedia.ca/Theatre-District-Chicago-Hotels-Luxury-Hotel.0-n651190586167894016-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Theatre District Hotels](https://www.expedia.ca/Theatre-District-Chicago-Hotels.0-n651190586167894016-0.Travel-Guide-Filter-Hotels) ### Flights - [Flights to Berwyn](https://www.expedia.ca/Cheap-Flights-To-Berwyn.d79328.Travel-Guide-Flights) - [Flights to Bridgeview](https://www.expedia.ca/Cheap-Flights-To-Bridgeview.d7045.Travel-Guide-Flights) - [Flights to Broadview](https://www.expedia.ca/Cheap-Flights-To-Broadview.d7064.Travel-Guide-Flights) - [Flights to Burbank](https://www.expedia.ca/Cheap-Flights-To-Burbank.d183178.Travel-Guide-Flights) - [Flights to Central Chicago](https://www.expedia.ca/Cheap-Flights-To-Central-Chicago.d553248635976475413.Travel-Guide-Flights) - [Flights to Chicago Ridge](https://www.expedia.ca/Cheap-Flights-To-Chicago-Ridge.d89160.Travel-Guide-Flights) - [Flights to Crestwood](https://www.expedia.ca/Cheap-Flights-To-Crestwood.d6960.Travel-Guide-Flights) - [Flights to Des Plaines](https://www.expedia.ca/Cheap-Flights-To-Des-Plaines.d7863.Travel-Guide-Flights) - [Flights to Elmhurst](https://www.expedia.ca/Cheap-Flights-To-Elmhurst.d7836.Travel-Guide-Flights) - [Flights to Elmwood Park](https://www.expedia.ca/Cheap-Flights-To-Elmwood-Park.d101509.Travel-Guide-Flights) - [Flights to Evanston](https://www.expedia.ca/Cheap-Flights-To-Evanston.d8049.Travel-Guide-Flights) - [Flights to Far Southwest Side](https://www.expedia.ca/Cheap-Flights-To-Far-Southwest-Side.d553248635976475353.Travel-Guide-Flights) - [Flights to Franklin Park](https://www.expedia.ca/Cheap-Flights-To-Franklin-Park.d180646.Travel-Guide-Flights) - [Flights to Glenview](https://www.expedia.ca/Cheap-Flights-To-Glenview.d8006.Travel-Guide-Flights) - [Flights to Hickory Hills](https://www.expedia.ca/Cheap-Flights-To-Hickory-Hills.d6132128.Travel-Guide-Flights) - [Flights to Hillside](https://www.expedia.ca/Cheap-Flights-To-Hillside.d8353.Travel-Guide-Flights) - [Flights to La Grange](https://www.expedia.ca/Cheap-Flights-To-La-Grange.d178165.Travel-Guide-Flights) - [Flights to Lyons](https://www.expedia.ca/Cheap-Flights-To-Lyons.d183188.Travel-Guide-Flights) - [Flights to McCook](https://www.expedia.ca/Cheap-Flights-To-McCook.d6132272.Travel-Guide-Flights) - [Flights to Midway Intl.](https://www.expedia.ca/Cheap-Flights-To-Midway-Intl.d5719117.Travel-Guide-Flights) - [Flights to North Side](https://www.expedia.ca/Cheap-Flights-To-North-Side.d553248635976475406.Travel-Guide-Flights) - [Flights to Northlake](https://www.expedia.ca/Cheap-Flights-To-Northlake.d55171.Travel-Guide-Flights) - [Flights to O'Hare Intl.](https://www.expedia.ca/Cheap-Flights-To-OHare-Intl.d4477519.Travel-Guide-Flights) - [Flights to Oak Brook](https://www.expedia.ca/Cheap-Flights-To-Oak-Brook.d9218.Travel-Guide-Flights) - [Flights to Oak Park](https://www.expedia.ca/Cheap-Flights-To-Oak-Park.d9228.Travel-Guide-Flights) - [Flights to Rosemont](https://www.expedia.ca/Cheap-Flights-To-Rosemont.d7581.Travel-Guide-Flights) - [Flights to Southwest Side](https://www.expedia.ca/Cheap-Flights-To-Southwest-Side.d553248635976475403.Travel-Guide-Flights) - [Flights to Wilmette](https://www.expedia.ca/Cheap-Flights-To-Wilmette.d54976.Travel-Guide-Flights) - [Flights to Winnetka](https://www.expedia.ca/Cheap-Flights-To-Winnetka.d175751.Travel-Guide-Flights) - [Flights to Worth](https://www.expedia.ca/Cheap-Flights-To-Worth.d176696.Travel-Guide-Flights) - [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) ### Packages - [Cibc Theatre](https://www.expedia.ca/CIBC-Theatre-Downtown-Chicago.d553248621563220853.Vacation-Attraction) - [Visit Downtown Chicago](https://www.expedia.ca/Chicago-Downtown-Chicago.dx6350699) - [Visit The Loop](https://www.expedia.ca/Chicago-The-Loop.dx800024) - [Millennium Park](https://www.expedia.ca/Millennium-Park-Downtown-Chicago.d6069201.Vacation-Attraction) - [Richard J. Daley Center](https://www.expedia.ca/Richard-J-Daley-Center-Downtown-Chicago.d6175173.Vacation-Attraction) - [The Loop Vacations](https://www.expedia.ca/The-Loop.d800024.Destination-Travel-Guides) ### Cars - [Alamo Rent A Car Rental Cars in The Loop](https://www.expedia.ca/Alamo-Rent-A-Car-Car-Rentals-In-The-Loop.d800024-c6.Car-Rental-Guide-Suppliers) - [Avis Rental Cars in The Loop](https://www.expedia.ca/Avis-Car-Rentals-In-The-Loop.d800024-c41.Car-Rental-Guide-Suppliers) - [Car rentals near Richard J. Daley Center](https://www.expedia.ca/Car-Rentals-In-Richard-J-Daley-Center.d6175173.Car-Rental-Guide) - [Car rentals near The Loop](https://www.expedia.ca/Car-Rentals-In-The-Loop.d800024.Car-Rental-Guide) - [Dollar Rent A Car Rental Cars in The Loop](https://www.expedia.ca/Dollar-Rent-A-Car-Car-Rentals-In-The-Loop.d800024-c43.Car-Rental-Guide-Suppliers) - [Enterprise Rental Cars in The Loop](https://www.expedia.ca/Enterprise-Car-Rentals-In-The-Loop.d800024-c15.Car-Rental-Guide-Suppliers) - [Fox Rental Cars Rental Cars in The Loop](https://www.expedia.ca/Fox-Rental-Cars-Car-Rentals-In-The-Loop.d800024-c19.Car-Rental-Guide-Suppliers) - [Oryx Rent A Car Rental Cars in The Loop](https://www.expedia.ca/ORYX-Rent-A-Car-Car-Rentals-In-The-Loop.d800024-c1059.Car-Rental-Guide-Suppliers) - [Payless Rental Cars in The Loop](https://www.expedia.ca/Payless-Car-Rentals-In-The-Loop.d800024-c38.Car-Rental-Guide-Suppliers) - [Rent A Wreck Rental Cars in The Loop](https://www.expedia.ca/Rent-A-Wreck-Car-Rentals-In-The-Loop.d800024-c33.Car-Rental-Guide-Suppliers) - [Routes Rental Cars in The Loop](https://www.expedia.ca/Routes-Car-Rentals-In-The-Loop.d800024-c1101.Car-Rental-Guide-Suppliers) - [Sixt Rental Cars in The Loop](https://www.expedia.ca/Sixt-Car-Rentals-In-The-Loop.d800024-c35.Car-Rental-Guide-Suppliers) - [Thrifty Car Rental Rental Cars in The Loop](https://www.expedia.ca/Thrifty-Car-Rental-Car-Rentals-In-The-Loop.d800024-c45.Car-Rental-Guide-Suppliers) \*Available to Expedia members.