Title: Cheap Flights to Historic Route 66 from CA $232 - Expedia.ca ![Woody Guthrie Center featuring outdoor art](https://images.trvl-media.com/place/553248621561870385/84ae69cd-06d7-48b8-a04a-f0221ac6efc7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_flights_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Cheap Flights to Historic Route 66 from CA $232 [View CA $232 flight on Sat, Nov 8, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YYZ,to:MDW,departure:08/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:231.89&airProductToken=AQpoCjII16YBEgQ2MzUzGJjOASDMfCjIwvwCMNzD_AI4TEAAWAFqBUVDT05PcghMT1VEMFpFUwoyCNemARIEODA1NhjMfCDssAEovMX8AjCcxvwCOExAAVgBagVFQ09OT3IITE9VRDBaRVMSCggBEAEYASoCV1MYASIECAEQASgCKAMoBDAB) - [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 [Historic Route 66 Travel Guide](https://expedia.ca/Historic-Route-66.dx702654640613646336)[Hotels in Historic Route 66](https://expedia.ca/Historic-Route-66-Hotels.d702654640613646336.Travel-Guide-Hotels)[Historic Route 66 Car Rentals](https://expedia.ca/Car-Rentals-In-Historic-Route-66.d702654640613646336.Car-Rental-Guide)[Historic Route 66 Vacation Packages](https://expedia.ca/Historic-Route-66.d702654640613646336.Destination-Travel-Guides) ## Popular airlines - ![Frontier Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines - ![Delta](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta - ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines - ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United - ![Spirit Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg) Spirit Airlines - ![Southwest Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines - ![Alaska Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines - ## Plan, book, fly with confidence - ### Be in the know Get alerts if flight prices drop or rise\* - ### Book smarter Save up to 30% on select hotels after you book a flight\* - ### 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 Historic Route 66? Prices were available within the past 7 days and start at CA $232 for one-way flights and CA $373 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Nov 5 - Mon, Nov 10 YYZ Toronto ORD Chicago CA $373 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:05/11/2025TANYT&leg2=from:ORD,to:YYZ,departure:10/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:372.95&airProductToken=AQqcAQozCMGCARIEMzEzNRiYzgEg4poBKLuj_AIwvKT8AjhCQABYAWoFQkFTSUNyCE9XQUNaTkJWCjIIwYIBEgQxNTAyGOKaASChAyiUqPwCMPmo_AI4QkABWAFqBUJBU0lDcghPV0FDWk5CVgoxCMGCARIEMzkwOBihAyCuHCiNrPwCMPus_AI4QkABWAFqBUJBU0lDcghPVkFJVlNCWAqcAQoxCMGCARIEMzg3OBiuHCChAyj84PwCMOLh_AI4QkAAWAFqBUJBU0lDcghPVkFJVlNCWAoyCMGCARIEMTc5NBihAyDimgEoquT8AjCC5fwCOEJAAVgBagVCQVNJQ3IIT1dBQ1pOQlYKMwjBggESBDMxMzUY4poBIJjOASjX5fwCMM7m_AI4QkABWAFqBUJBU0lDcghPV0FDWk5CVhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Mon, Dec 15 - Tue, Dec 16 YYZ Toronto MDW Chicago CA $379 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:MDW,departure:15/12/2025TANYT&leg2=from:MDW,to:YYZ,departure:16/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:378.81&airProductToken=AQpGCiEI16YBEgQ2NzY4GJjOASDgXCiu6P8CMMrp_wI4TEAAWAEKIQjXpgESBDcyNjMY4Fwg7LABKKTv_wIwmvD_AjhMQAFYAQpGCiEI16YBEgQ3NzA2GOywASDMfCiG8v8CMOry_wI4TEAAWAEKIQjXpgESBDYzMjIYzHwgmM4BKP30_wIwi_b_AjhMQAFYARIKCAEQARgBKgJXUxgBIgQIARABKAQwAQ) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Tue, Oct 28 - Tue, Nov 4 YUL Montreal ORD Chicago CA $392 Roundtrip found 20 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YUL,to:ORD,departure:28/10/2025TANYT&leg2=from:ORD,to:YUL,departure:04/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:391.37&airProductToken=AQoyCjAIwYYBEgM1MjEYmF0grhwo5cf7AjCSyfsCOEdAAFgBagVCQVNJQ3IIR05BMkE3QkEKMwoxCMGGARIEODk1OBiuHCCYXSi7lvwCMLiX_AI4R0AAWAFqBUJBU0lDcghHTkEyQTdCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMAE) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Fri, Nov 21 - Fri, Nov 28 YUL Montreal MDW Chicago CA $392 Roundtrip found 20 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YUL,to:MDW,departure:21/11/2025TANYT&leg2=from:MDW,to:YUL,departure:28/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:391.37&airProductToken=AQppCjII0IgBEgQyNDUyGJhdIPjMASiB1f0CMNbV_QI4TUAAWAFqBUJBU0lDcghNMk4wWlJaTAozCNCIARIEMjM4Nxj4zAEg7LABKJfW_QIwhdf9AjhNQAFYAWoFQkFTSUNyCE0yTjBaUlpMCmkKMwjQiAESBDIzODgY7LABIPjMASicpv4CMIKn_gI4TUAAWAFqBUJBU0lDcghNMk4wWlJaTAoyCNCIARIEMjQ3ORj4zAEgmF0o36f-AjCqqP4COE1AAVgBagVCQVNJQ3IITTJOMFpSWkwSCggBEAEYASoCUEQYASIECAEQASgCKAMoBDAB) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sat, Nov 1 - Sun, Nov 2 YUL Montreal ORD Chicago CA $392 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YUL,to:ORD,departure:01/11/2025TANYT&leg2=from:ORD,to:YUL,departure:02/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:391.48&airProductToken=AQo2CjQI1YIBEgQzNTQ5GJhdIK4cKJ34-wIw0fn7AjhOQABYAWoIRUNPQkFTSUNyCEdBQTJBRkJTCjYKNAjVggESBDM0MTgYrhwgmF0oxoH8AjDUgvwCOE5AAFgBaghFQ09CQVNJQ3IIR0FBMkFGQlMSCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAB) ## Find the cheapest month to fly from Columbus (CMH) to Chicago (ORD) ### July is typically the cheapest month to fly From CA $107 - CA $363 per traveller. Expedia.ca gives you the best tools to secure great deals on flights to Historic Route 66. 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 Historic Route 66. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Historic Route 66. 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 Historic Route 66 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 Historic Route 66. Looking to save even more? Get additional savings by bundling your Historic Route 66 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 Historic Route 66 trip! Flights to Historic Route 66 information | Destination airport | O'Hare Intl. | | --- | --- | | Destination airport IATA code | ORD | | Destination city name | Chicago | | Roundtrip price | CA $373 | ## Need more than a Flight to Historic Route 66? Heading to Historic Route 66? Explore Historic Route 66 with Expedia's Travel Guides to find the best hotels, vacation packages, car rental deals and more! [Historic Route 66 Hotels](https://expedia.ca/Historic-Route-66-Hotels.d702654640613646336.Travel-Guide-Hotels)[Historic Route 66 Vacation Rentals](https://expedia.ca/Historic-Route-66-Vacation-Rentals.d702654640613646336.Travel-Guide-VacationRentals)[Historic Route 66 Car Rentals](https://expedia.ca/Car-Rentals-In-Historic-Route-66.d702654640613646336.Car-Rental-Guide)[Historic Route 66 Vacations](https://expedia.ca/Historic-Route-66.d702654640613646336.Destination-Travel-Guides) ## Trending flights to Historic Route 66 Prices were available within the past 7 days and start at CA $232 for one-way flights and CA $373 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Nov 5 - Mon, Nov 10 YYZ Toronto ORD Chicago CA $373 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:05/11/2025TANYT&leg2=from:ORD,to:YYZ,departure:10/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:372.95&airProductToken=AQqcAQozCMGCARIEMzEzNRiYzgEg4poBKLuj_AIwvKT8AjhCQABYAWoFQkFTSUNyCE9XQUNaTkJWCjIIwYIBEgQxNTAyGOKaASChAyiUqPwCMPmo_AI4QkABWAFqBUJBU0lDcghPV0FDWk5CVgoxCMGCARIEMzkwOBihAyCuHCiNrPwCMPus_AI4QkABWAFqBUJBU0lDcghPVkFJVlNCWAqcAQoxCMGCARIEMzg3OBiuHCChAyj84PwCMOLh_AI4QkAAWAFqBUJBU0lDcghPVkFJVlNCWAoyCMGCARIEMTc5NBihAyDimgEoquT8AjCC5fwCOEJAAVgBagVCQVNJQ3IIT1dBQ1pOQlYKMwjBggESBDMxMzUY4poBIJjOASjX5fwCMM7m_AI4QkABWAFqBUJBU0lDcghPV0FDWk5CVhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ## Explore a world of travel with Expedia - 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[Spa Hotels in Quad Cities](https://www.expedia.ca/Quad-Cities-Hotels-Spa-Hotel.0-0-d603001-tSpaHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Quad Cities](https://www.expedia.ca/Quad-Cities-Hotels-Waterpark-Hotels.0-0-d603001-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Quad Cities Hotels](https://www.expedia.ca/Quad-Cities-Hotels.d603001.Travel-Guide-Hotels) - [B&B in Southeast Iowa](https://www.expedia.ca/Southeast-Iowa-Bed-And-Breakfast.d6234151-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Americinn Hotels in Southeast Iowa](https://www.expedia.ca/Southeast-Iowa-Hotels-Americinn.0-0-d6234151--bAmericinn.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Southeast Iowa](https://www.expedia.ca/Southeast-Iowa-Hotels-Luxury-Hotel.0-0-d6234151-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Southeast Iowa](https://www.expedia.ca/Southeast-Iowa-Hotels-Pet-Friendly-Hotel.0-0-d6234151-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Southeast Iowa](https://www.expedia.ca/Southeast-Iowa-Hotels-Romantic-Hotel.0-0-d6234151-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Southeast Iowa Hotels](https://www.expedia.ca/Southeast-Iowa-Hotels.d6234151.Travel-Guide-Hotels) ### Flights - [Flights to Ohio River Valley](https://www.expedia.ca/Cheap-Flights-To-Ohio-River-Valley.d6233674.Travel-Guide-Flights) - [Flights to Quad Cities](https://www.expedia.ca/Cheap-Flights-To-Quad-Cities.d603001.Travel-Guide-Flights) - [Flights to Southeast Iowa](https://www.expedia.ca/Cheap-Flights-To-Southeast-Iowa.d6234151.Travel-Guide-Flights) - [Flights from Calgary to Quad Cities](https://www.expedia.ca/lp/flights/178245/603001/calgary-to-quad-cities) - [Flights from Calgary to Ohio River Valley](https://www.expedia.ca/lp/flights/178245/6233674/calgary-to-ohio-river-valley) - [Flights from Chicago to Quad Cities](https://www.expedia.ca/lp/flights/178248/603001/chicago-to-quad-cities) - [Flights from Columbus to Quad Cities](https://www.expedia.ca/lp/flights/178251/603001/columbus-to-quad-cities) - [Flights from Dallas to Ohio River Valley](https://www.expedia.ca/lp/flights/178253/6233674/dallas-to-ohio-river-valley) - [Flights from Indianapolis to Quad Cities](https://www.expedia.ca/lp/flights/178266/603001/indianapolis-to-quad-cities) - [Flights from Miami to Ohio River Valley](https://www.expedia.ca/lp/flights/178286/6233674/miami-to-ohio-river-valley) - [Flights from Minneapolis - St. Paul to Quad Cities](https://www.expedia.ca/lp/flights/178287/603001/minneapolis-st-paul-to-quad-cities) - [Flights from Minneapolis - St. Paul to Ohio River Valley](https://www.expedia.ca/lp/flights/178287/6233674/minneapolis-st-paul-to-ohio-river-valley) - [Flights from Orlando to Ohio River Valley](https://www.expedia.ca/lp/flights/178294/6233674/orlando-to-ohio-river-valley) - [Flights from Seattle to Quad Cities](https://www.expedia.ca/lp/flights/178307/603001/seattle-to-quad-cities) - [Flights from Toronto to Quad Cities](https://www.expedia.ca/lp/flights/178314/603001/toronto-to-quad-cities) - [Flights from Toronto to Ohio River Valley](https://www.expedia.ca/lp/flights/178314/6233674/toronto-to-ohio-river-valley) - [Flights from Vancouver to Ohio River Valley](https://www.expedia.ca/lp/flights/178315/6233674/vancouver-to-ohio-river-valley) - [Flights from Edmonton to Quad Cities](https://www.expedia.ca/lp/flights/180002/603001/edmonton-to-quad-cities) - [Flights from Edmonton to Ohio River Valley](https://www.expedia.ca/lp/flights/180002/6233674/edmonton-to-ohio-river-valley) - [Flights from Québec City to Ohio River Valley](https://www.expedia.ca/lp/flights/180017/6233674/quebec-city-to-ohio-river-valley) - [Flights from Amarillo to Quad Cities](https://www.expedia.ca/lp/flights/371/603001/amarillo-to-quad-cities) - [Flights from Hamilton to Quad Cities](https://www.expedia.ca/lp/flights/3963/603001/hamilton-to-quad-cities) - [Flights from Fort Lauderdale to Ohio River Valley](https://www.expedia.ca/lp/flights/601750/6233674/fort-lauderdale-to-ohio-river-valley) - [Flights from Newark to Ohio River Valley](https://www.expedia.ca/lp/flights/601760/6233674/newark-to-ohio-river-valley) - [Flights from Buffalo to Quad Cities](https://www.expedia.ca/lp/flights/602674/603001/buffalo-to-quad-cities) - [Flights from Buffalo to Ohio River Valley](https://www.expedia.ca/lp/flights/602674/6233674/buffalo-to-ohio-river-valley) - [Flights from Birmingham to Ohio River Valley](https://www.expedia.ca/lp/flights/602981/6233674/birmingham-to-ohio-river-valley) - [Flights from Quad Cities](https://www.expedia.ca/lp/flights/603001/flights-from-quad-cities) - [Flights from Winnipeg to Quad Cities](https://www.expedia.ca/lp/flights/6141041/603001/winnipeg-to-quad-cities) - [Flights from Ohio River Valley](https://www.expedia.ca/lp/flights/6233674/flights-from-ohio-river-valley) ### Packages - [Lake Michigan](https://www.expedia.ca/Lake-Michigan-United-States-of-America.d6338716.Vacation-Attraction) - [Visit Ohio River Valley](https://www.expedia.ca/Ohio-River-Valley.dx6233674) - [Quad Cities Vacations](https://www.expedia.ca/Quad-Cities.d603001.Destination-Travel-Guides) - [Visit Quad Cities](https://www.expedia.ca/Quad-Cities.dx603001) - [Visit Southeast Iowa](https://www.expedia.ca/Southeast-Iowa.dx6234151) ### Cars - [Ace Rental Cars in Quad Cities](https://www.expedia.ca/Ace-Car-Rentals-In-Quad-Cities.d603001-c2.Car-Rental-Guide-Suppliers) - [Advantage Rent-A-Car Rental Cars in Ohio River Valley](https://www.expedia.ca/Advantage-Rent-A-Car-Car-Rentals-In-Ohio-River-Valley.d6233674-c3.Car-Rental-Guide-Suppliers) - [Avis Rental Cars in Quad Cities](https://www.expedia.ca/Avis-Car-Rentals-In-Quad-Cities.d603001-c41.Car-Rental-Guide-Suppliers) - [Car rentals near Quad Cities](https://www.expedia.ca/Car-Rentals-In-Quad-Cities.d603001.Car-Rental-Guide) - [Pickup Car Rentals in Ohio River Valley](https://www.expedia.ca/Pickup-Car-Rentals-In-Ohio-River-Valley.d6233674-tPickup.Car-Rental-Guide-Class) - [Thrifty Car Rental Rental Cars in Ohio River Valley](https://www.expedia.ca/Thrifty-Car-Rental-Car-Rentals-In-Ohio-River-Valley.d6233674-c45.Car-Rental-Guide-Suppliers) ### Other - [Things to do in Quad Cities](https://www.expedia.ca/Things-To-Do-In-Quad-Cities.d603001.Travel-Guide-Activities) \*Available to Expedia members.