Title: CA $256 Cheap American Airlines fights from Chicago to Key West - Expedia.ca ![](https://images.trvl-media.com/place/1187/a7c3fad3-5f12-4d91-8996-ed0e1b61b0a3.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) # CA $256 Cheap American Airlines fights from Chicago (ORD) to Key West (EYW) [View CA $256 flight on Thu, Feb 19, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:ORD,to:EYW,departure:19/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:255.70&airProductToken=AQpnCjEIwYIBEgQyOTQwGK4cIIwCKK_NhQMw7s6FAzhCQABYAWoFQkFTSUNyCE83QVdaU0JaCjIIwYIBEgQzOTg4GIwCIIS2ASiJ0YUDMMvRhQM4QkABWAFqBUJBU0lDcghPN0FXWlNCWhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) - [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 ![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) ## American Airlines flights from Chicago to Key West (ORD→EYW) Prices were available within the past 7 days and start at CA $256 for one-way flights and CA $518 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, Oct 29 - Sat, Nov 1 ORD Chicago EYW Key West CA $518 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:EYW,departure:29/10/2025TANYT&leg2=from:EYW,to:ORD,departure:01/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:517.20&airProductToken=AQpnCjEIwYIBEgQyMjQ3GK4cIIwCKPrT-wIwstX7AjhCQABYAWoFQkFTSUNyCFMwRldVTkJYCjIIwYIBEgQzODk1GIwCIIS2ASip1vsCMNzW-wI4QkABWAFqBUJBU0lDcghTMEZXVU5CWAplCjEIwYIBEgQ0NTcwGIS2ASBDKJr2-wIwxPf7AjhCQABYAWoFQkFTSUNyCFMwRldVTkJYCjAIwYIBEgQxNjM3GEMgrhwo5vf7AjD1-PsCOEJAAVgBagVCQVNJQ3IIUzBGV1VOQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Oct 29 - Sat, Nov 1 ORD Chicago EYW Key West CA $546 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:EYW,departure:29/10/2025TANYT&leg2=from:EYW,to:ORD,departure:01/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:545.20&airProductToken=AQppCjIIwYIBEgQxNzg0GK4cIOKaASi60vsCMLrT-wI4QkAAWAFqBUJBU0lDcghTMEZXVU5CWAozCMGCARIEMzMzOBjimgEghLYBKLTU-wIwxtX7AjhCQAFYAWoFQkFTSUNyCFMwRldVTkJYCmgKMwjBggESBDM4OTAYhLYBIOKaASip-PsCML35-wI4QkAAWAFqBUJBU0lDcghHMEZXVU5CWAoxCMGCARIDODE1GOKaASCuHCjv-fsCMPH6-wI4QkABWAFqBUJBU0lDcghHMEZXVU5CWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Dec 4 - Sun, Dec 7 ORD Chicago EYW Key West CA $565 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:EYW,departure:04/12/2025TANYT&leg2=from:EYW,to:ORD,departure:07/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:564.50&airProductToken=AQpnCjEIwYIBEgQxMTgyGK4cIIwCKLjr_gIwhe3-AjhCQABYAWoFQkFTSUNyCE5XRldaTkJYCjIIwYIBEgQ0MDUxGIwCIIS2ASiv7v4CMPfu_gI4QkABWAFqBUJBU0lDcghOV0ZXWk5CWApnCjIIwYIBEgQ0MDY0GIS2ASCMAiihj_8CMNSP_wI4QkAAWAFqBUJBU0lDcghOV0ZXWk5CWAoxCMGCARIEMTIxORiMAiCuHCifkP8CMO2R_wI4QkABWAFqBUJBU0lDcghOV0ZXWk5CWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Oct 29 - Sat, Nov 1 ORD Chicago EYW Key West CA $574 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:EYW,departure:29/10/2025TANYT&leg2=from:EYW,to:ORD,departure:01/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:573.10&airProductToken=AQppCjIIwYIBEgQyODk2GK4cIKOxASih0vsCMLzT-wI4QkAAWAFqBUJBU0lDcghHMEZXVU5CWAozCMGCARIEMTgxNBijsQEghLYBKPrU-wIwotb7AjhCQAFYAWoFQkFTSUNyCEcwRldVTkJYCmYKMgjBggESBDM2ODkYhLYBIIwCKNj5-wIwiPr7AjhCQABYAWoFQkFTSUNyCEcwRldVTkJYCjAIwYIBEgM0ODMYjAIgrhwoxPr7AjCK_PsCOEJAAVgBagVCQVNJQ3IIRzBGV1VOQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Fri, Oct 31 - Tue, Nov 11 ORD Chicago EYW Key West CA $603 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:EYW,departure:31/10/2025TANYT&leg2=from:EYW,to:ORD,departure:11/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:603.00&airProductToken=AQpnCiAIwYIBEgQxODcyGK4cIO9ZKOHo-wIw2en7AjhOQABYAQogCMGCARIEMTI4MxjvWSCMAiiV6vsCMMjr-wI4TkABWAEKIQjBggESBDM4OTUYjAIghLYBKOns-wIwnO37AjhOQAFYAQpECiEIwYIBEgQ0MDY0GIS2ASCMAijV6vwCMIjr_AI4U0AAWAEKHwjBggESAzg0MhiMAiCuHCjb6_wCMK3t_AI4U0ABWAESCggBEAEYASoCQUEYASIECAEQASgIKAQwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Oct 29 - Sat, Nov 1 ORD Chicago EYW Key West CA $610 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:EYW,departure:29/10/2025TANYT&leg2=from:EYW,to:ORD,departure:01/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:609.70&airProductToken=AQpnCjEIwYIBEgQyMjQ3GK4cIIwCKPrT-wIwstX7AjhCQABYAWoFQkFTSUNyCFMwRldVTkJYCjIIwYIBEgQzODk1GIwCIIS2ASip1vsCMNzW-wI4QkABWAFqBUJBU0lDcghTMEZXVU5CWAppCjMIwYIBEgQyNjc3GIS2ASDimgEosvb7AjC99_sCOEJAAFgBagVCQVNJQ3IITDBGV1VOQloKMgjBggESBDExOTkY4poBIK4cKOj4-wIw6_n7AjhCQAFYAWoFQkFTSUNyCEwwRldVTkJaEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) Flight from Chicago to Key West (ORD - EYW) route information | Origin airport | O'Hare Intl. | | --- | --- | | Destination airport | Key West Intl. | | Airlines serving | American Airlines, United | | Popular airline | United | | Distance | 2006 km | ## Frequently asked questions ### How much is an American Airlines flight from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)? > You can find cheap round-trip American Airlines flights from CA $518 from ORD to EYW by sorting your results from "Price (lowest to highest)" on Expedia. Or look for options from CA $256 for a one-way journey.\**\*These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.* ### What is the cheapest month to fly from ORD to EYW with American Airlines? > September is one of the least expensive months to fly to Key West with American Airlines. You could also find excellent prices on one-way and round-trip fares in August. ### Does American Airlines fly nonstop from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)? > Hop on one of American Airlines's 7 weekly direct flights from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW). To view available options, enter your destination, origin and dates and hit search. Then use the "Nonstop" and "Airline" filters. ### How long does it take to fly from ORD to EYW with American Airlines? > Depart O'Hare Intl. Airport (ORD) for Key West Intl. Airport (EYW) on a direct American Airlines flight, and you'll be in the skies for about 3h 24m. ### What airports does American Airlines fly into in Key West? > American Airlines flights from O'Hare Intl. Airport (ORD) to Key West come in to Key West Intl. Airport (EYW). This is the main gateway here. ### What type of plane does American Airlines fly from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)? > Set off on an American Airlines flight from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW), and you'll probably board an Embraer 170. Keep in mind though, that the aircraft type can change due to operational reasons. ### Can I change or cancel my American Airlines flight from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)? > Typically, you can cancel or change your flight, although there may be additional charges if your booking was made over 24 hours ago. Prefer to keep your options open? Use Expedia's "Changes included" and "No cancel fee" filters to find flights that won't charge extra if you need to alter your plans. 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[Waterpark Hotels in New Town](https://www.expedia.ca/New-Town-Key-West-Hotels-Waterpark-Hotels.0-n553248635976480351-0-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [New Town Hotels](https://www.expedia.ca/New-Town-Key-West-Hotels.0-n553248635976480351-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Northside Resort](https://www.expedia.ca/Northside-Resort-Key-West-Hotels-Cheap-Hotels.0-n864982599800745984-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Northside Resort Hotels](https://www.expedia.ca/Northside-Resort-Key-West-Hotels.0-n864982599800745984-0.Travel-Guide-Filter-Hotels) - [Hotels near Robbie's](https://www.expedia.ca/Robbies-Hotels.0-l6068603-0.Travel-Guide-Filter-Hotels) - [Hotels near Smathers Beach](https://www.expedia.ca/Smathers-Beach-Hotels.0-l6069255-0.Travel-Guide-Filter-Hotels) - [B&B in Stock Island](https://www.expedia.ca/Stock-Island-Bed-And-Breakfast.d180166-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Stock Island](https://www.expedia.ca/Stock-Island-Hotels-Beach-Hotel.0-0-d180166-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Stock Island](https://www.expedia.ca/Stock-Island-Hotels-Boutique-Hotel.0-0-d180166-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Stock Island](https://www.expedia.ca/Stock-Island-Hotels-Cheap-Hotels.0-0-d180166-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Stock Island](https://www.expedia.ca/Stock-Island-Hotels-Family-Hotel.0-0-d180166-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Stock Island](https://www.expedia.ca/Stock-Island-Hotels-Hotels-With-Bar.0-0-d180166-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Stock Island](https://www.expedia.ca/Stock-Island-Hotels-Pet-Friendly-Hotel.0-0-d180166-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Stock Island](https://www.expedia.ca/Stock-Island-Hotels-Romantic-Hotel.0-0-d180166-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Stock Island Hotels](https://www.expedia.ca/Stock-Island-Hotels.d180166.Travel-Guide-Hotels) - [Houseboats in Stock Island](https://www.expedia.ca/Stock-Island-Houseboats.d180166-aaHouseboats.Travel-Guide-Accommodation) - [Vacation Homes in Stock Island](https://www.expedia.ca/Stock-Island-Private-Vacation-Homes.d180166-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Resorts in Stock Island](https://www.expedia.ca/Stock-Island-Resort-Hotels.d180166-aaResortHotels.Travel-Guide-Accommodation) ### Flights - [Flights to Stock Island](https://www.expedia.ca/Cheap-Flights-To-Stock-Island.d180166.Travel-Guide-Flights) - [Hopscotch Air St. Petersburg (SPG) to Marathon (MTH) flights](https://www.expedia.ca/lp/flight-routes/hopscotch-air-from-albert-whitted-to-florida-keys-marathon/o2/spg/mth) - [Flights from Houston to Stock Island](https://www.expedia.ca/lp/flights/178265/180166/houston-to-stock-island) - [Flights from Miami to Stock Island](https://www.expedia.ca/lp/flights/178286/180166/miami-to-stock-island) - [Flights from Vancouver to Stock Island](https://www.expedia.ca/lp/flights/178315/180166/vancouver-to-stock-island) - [Flights from Stock Island](https://www.expedia.ca/lp/flights/180166/flights-from-stock-island) - [Flights from Milwaukee to Stock Island](https://www.expedia.ca/lp/flights/602647/180166/milwaukee-to-stock-island) ### Packages - [Visit Cow Key](https://www.expedia.ca/Cow-Key.dx180163) - [Fort East Martello Museum and Gallery](https://www.expedia.ca/Fort-East-Martello-Museum-And-Gallery-Key-West.d6069253.Vacation-Attraction) - [Visit Northside Resort](https://www.expedia.ca/Key-West-Northside-Resort.dx864982599800745984) - [Key West Vacations](https://www.expedia.ca/Key-West.d1187.Destination-Travel-Guides) - [Smathers Beach](https://www.expedia.ca/Smathers-Beach-Beachside.d6069255.Vacation-Attraction) - [Stock Island Vacations](https://www.expedia.ca/Stock-Island.d180166.Destination-Travel-Guides) - [Visit Stock Island](https://www.expedia.ca/Stock-Island.dx180166) ### Cars - [Ada Rental Cars in Stock Island](https://www.expedia.ca/ADA-Car-Rentals-In-Stock-Island.d180166-c1109.Car-Rental-Guide-Suppliers) - [Avis Canaries Rental Cars in Stock Island](https://www.expedia.ca/Avis-Canaries-Car-Rentals-In-Stock-Island.d180166-c1135.Car-Rental-Guide-Suppliers) - [Budget Rental Cars in Stock Island](https://www.expedia.ca/Budget-Car-Rentals-In-Stock-Island.d180166-c39.Car-Rental-Guide-Suppliers) - [Fox Rental Cars Rental Cars in Stock Island](https://www.expedia.ca/Fox-Rental-Cars-Car-Rentals-In-Stock-Island.d180166-c19.Car-Rental-Guide-Suppliers) - [Rentacar Guadeloupe Rental Cars in Stock Island](https://www.expedia.ca/RentACar-Guadeloupe-Car-Rentals-In-Stock-Island.d180166-c1103.Car-Rental-Guide-Suppliers) ### Other - [Things to do in Key West](https://www.expedia.ca/Things-To-Do-In-Key-West.d1187.Travel-Guide-Activities) - [Things to do in Stock Island](https://www.expedia.ca/Things-To-Do-In-Stock-Island.d180166.Travel-Guide-Activities) \*Available to Expedia members.