Title: Cheap Flights from Chicago (CHI) to Key West (EYW) - 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) # Cheap Flights from Chicago (CHI) to Key West (EYW) - [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 ## Popular airlines from Chicago to Key West, FL (EYW-Key West Intl.) - ![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:chi,to:eyw,departure:21/10/2025TANYT&leg2=from:eyw,to:chi,departure:28/10/2025TANYT&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:chi,to:eyw,departure:21/10/2025TANYT&leg2=from:eyw,to:chi,departure:28/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![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:chi,to:eyw,departure:21/10/2025TANYT&leg2=from:eyw,to:chi,departure:28/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![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:chi,to:eyw,departure:21/10/2025TANYT&leg2=from:eyw,to:chi,departure:28/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ![JetBlue Airways](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways [](https://www.expedia.ca/Flights-Search?leg1=from:chi,to:eyw,departure:21/10/2025TANYT&leg2=from:eyw,to:chi,departure:28/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) ![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) ## Cheap flights from Chicago (CHI) to Key West (EYW) Prices were available within the past 7 days and start at for one-way flights and CA $374 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Oct 25 - Wed, Oct 29 MDW Chicago EYW Key West CA $374 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MDW,to:EYW,departure:25/10/2025TANYT&leg2=from:EYW,to:MDW,departure:29/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:373.80&airProductToken=AQpGCiEIxJgBEgQxMDYzGOywASDgXCiHp_sCMPmn-wI4RUAAWAEKIQjEmAESBDIxNjgY4FwghLYBKPOo-wIw4an7AjhFQAFYAQpGCiEIxJgBEgQxMjgxGIS2ASDgXCi21PsCMLDV-wI4RUAAWAEKIQjEmAESBDIwNjAY4Fwg7LABKOPV-wIw1db7AjhFQAFYARIKCAEQARgBKgJETBgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Oct 27 - Mon, Nov 3 ORD Chicago EYW Key West CA $374 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:EYW,departure:27/10/2025TANYT&leg2=from:EYW,to:ORD,departure:03/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:373.80&airProductToken=AQpFCiAIxJgBEgQxMjY0GK4cIOBcKIy7-wIw_7v7AjhFQABYAQohCMSYARIEMTI4MRjgXCCEtgEoz7z7AjC_vfsCOEVAAVgBCkUKIQjEmAESBDIxNjgYhLYBIOBcKPWP_AIw9ZD8AjhFQABYAQogCMSYARIEMTE5ORjgXCCuHCiQkvwCMIaT_AI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Oct 27 - Sat, Nov 1 ORD Chicago EYW Key West CA $402 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:EYW,departure:27/10/2025TANYT&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:401.80&airProductToken=AQpFCiAIxJgBEgQxMjY0GK4cIOBcKIy7-wIw_7v7AjhFQABYAQohCMSYARIEMTI4MRjgXCCEtgEoz7z7AjC_vfsCOEVAAVgBCkUKIQjEmAESBDE0NzIYhLYBIOBcKPX2-wIw7vf7AjhFQABYAQogCMSYARIEMjg3ORjgXCCuHCjS-PsCMNX5-wI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sun, Oct 26 - Tue, Nov 4 MDW Chicago EYW Key West CA $428 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MDW,to:EYW,departure:26/10/2025TANYT&leg2=from:EYW,to:MDW,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:427.30&airProductToken=AQpGCiEIxJgBEgQyNDAwGOywASDgXCiUsPsCMIix-wI4RUAAWAEKIQjEmAESBDEyODEY4FwghLYBKK-x-wIwn7L7AjhFQAFYAQpqCiEIxJgBEgQyMTY4GIS2ASDgXCiVm_wCMJWc_AI4RUAAWAEKIQjEmAESBDI5NDAY4Fwg47QBKKCd_AIwlZ78AjhFQAFYAQoiCMSYARIENTI5OBjjtAEg7LABKMuj_AIwlKT8AjhFQAFYARIKCAEQARgBKgJETBgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Oct 31 - Sat, Nov 1 ORD Chicago EYW Key West CA $429 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:EYW,departure:31/10/2025TANYT&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:428.70&airProductToken=AQpFCiAIxJgBEgQxNDU2GK4cIOBcKPLr-wIw6-z7AjhFQABYAQohCMSYARIEMjgxNRjgXCCEtgEo1-37AjDG7vsCOEVAAVgBCkUKIQjEmAESBDE0NzIYhLYBIOBcKPX2-wIw7vf7AjhFQABYAQogCMSYARIEMjg3ORjgXCCuHCjS-PsCMNX5-wI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Oct 27 - Sat, Nov 15 ORD Chicago EYW Key West CA $445 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:EYW,departure:27/10/2025TANYT&leg2=from:EYW,to:ORD,departure:15/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:444.80&airProductToken=AQpFCiAIxJgBEgQxMjY0GK4cIOBcKIy7-wIw_7v7AjhFQABYAQohCMSYARIEMTI4MRjgXCCEtgEoz7z7AjC_vfsCOEVAAVgBCkUKIQjEmAESBDIxNjgYhLYBIOBcKPaW_QIw_Jf9AjhFQABYAQogCMSYARIEMTEzORjgXCCuHCi2mP0CMK6Z_QI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Nov 8 - Sun, Nov 23 ORD Chicago EYW Key West CA $451 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:EYW,departure:08/11/2025TANYT&leg2=from:EYW,to:ORD,departure:23/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:450.20&airProductToken=AQpFCiAIxJgBEgQxNDU2GK4cIOBcKK7G_AIwqMf8AjhFQABYAQohCMSYARIEMjgxNRjgXCCEtgEok8j8AjCCyfwCOEVAAVgBCkUKIQjEmAESBDEwNzIYhLYBIOBcKPjr_QIw-ez9AjhFQABYAQogCMSYARIEMTQ1NhjgXCCuHCjA7f0CMLzu_QI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sun, Nov 9 - Thu, Nov 20 ORD Chicago EYW Key West CA $458 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:EYW,departure:09/11/2025TANYT&leg2=from:EYW,to:ORD,departure:20/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:457.60&airProductToken=AQojCiEI1YIBEgQzNjg1GK4cIIS2ASi80PwCMIPS_AI4S0AAWAEKIwohCNWCARIEMzU3MBiEtgEgrhwojM79AjDuz_0COEtAAFgBEgoIARABGAEqAlVBGAEiBAgBEAEoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Nov 8 - Thu, Nov 27 ORD Chicago EYW Key West CA $469 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:EYW,departure:08/11/2025TANYT&leg2=from:EYW,to:ORD,departure:27/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:468.40&airProductToken=AQpFCiAIxJgBEgQxNDU2GK4cIOBcKK7G_AIwqMf8AjhFQABYAQohCMSYARIEMjgxNRjgXCCEtgEok8j8AjCCyfwCOEVAAVgBCkUKIQjEmAESBDE0NzIYhLYBIOBcKK6c_gIwrZ3-AjhFQABYAQogCMSYARIEMjg3ORjgXCCuHCjSnf4CMNSe_gI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Oct 24 - Wed, Oct 29 MDW Chicago EYW Key West CA $471 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MDW,to:EYW,departure:24/10/2025TANYT&leg2=from:EYW,to:MDW,departure:29/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:470.60&airProductToken=AQpGCiEIxJgBEgQyNDE3GOywASDgXCjsnPsCMN-d-wI4RUAAWAEKIQjEmAESBDI4MTUY4FwghLYBKPee-wIw5p_7AjhFQAFYAQpGCiEIxJgBEgQxMjgxGIS2ASDgXCi21PsCMLDV-wI4RUAAWAEKIQjEmAESBDIwNjAY4Fwg7LABKOPV-wIw1db7AjhFQAFYARIKCAEQARgBKgJETBgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Oct 31 - Sat, Nov 15 ORD Chicago EYW Key West CA $473 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:EYW,departure:31/10/2025TANYT&leg2=from:EYW,to:ORD,departure:15/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:472.70&airProductToken=AQpFCiAIxJgBEgQxNDU2GK4cIOBcKPLr-wIw6-z7AjhFQABYAQohCMSYARIEMjgxNRjgXCCEtgEo1-37AjDG7vsCOEVAAVgBCkUKIQjEmAESBDIxNjgYhLYBIOBcKPaW_QIw_Jf9AjhFQABYAQogCMSYARIEMTEzORjgXCCuHCi2mP0CMK6Z_QI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Nov 7 - Sun, Nov 23 ORD Chicago EYW Key West CA $479 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:EYW,departure:07/11/2025TANYT&leg2=from:EYW,to:ORD,departure:23/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:478.10&airProductToken=AQpFCiAIxJgBEgQxMjY0GK4cIOBcKKi3_AIwm7j8AjhFQABYAQohCMSYARIEMTQ3MhjgXCCEtgEozLn8AjC6uvwCOEVAAVgBCkUKIQjEmAESBDEwNzIYhLYBIOBcKPjr_QIw-ez9AjhFQABYAQogCMSYARIEMTQ1NhjgXCCuHCjA7f0CMLzu_QI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Nov 4 - Fri, Nov 7 MDW Chicago EYW Key West CA $497 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MDW,to:EYW,departure:04/11/2025TANYT&leg2=from:EYW,to:MDW,departure:07/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:496.10&airProductToken=AQpGCiEIxJgBEgQxMDYzGOywASDgXCiImPwCMPqY_AI4RUAAWAEKIQjEmAESBDIxNjgY4FwghLYBKO-Z_AIw3Zr8AjhFQAFYAQpqCiEIxJgBEgQyMTY4GIS2ASDgXCj1vPwCMPW9_AI4RUAAWAEKIQjEmAESBDI5NDAY4Fwg47QBKI-__AIwhMD8AjhFQAFYAQoiCMSYARIEMzg1OBjjtAEg7LABKMXD_AIwkMT8AjhFQAFYARIKCAEQARgBKgJETBgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Oct 14 - Sat, Oct 25 MDW Chicago EYW Key West CA $499 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MDW,to:EYW,departure:14/10/2025TANYT&leg2=from:EYW,to:MDW,departure:25/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:498.50&airProductToken=AQpGCiEIxJgBEgQyNDAwGOywASDgXCiUqfoCMIiq-gI4RUAAWAEKIQjEmAESBDEyODEY4FwghLYBKK-q-gIwn6v6AjhFQAFYAQpGCiEIxJgBEgQyMTY4GIS2ASDgXCiZqvsCMJmr-wI4RUAAWAEKIQjEmAESBDEwNzYY4Fwg7LABKNCr-wIwwqz7AjhFQAFYARIKCAEQARgBKgJETBgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Nov 1 - Sat, Nov 15 ORD Chicago EYW Key West CA $516 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:EYW,departure:01/11/2025TANYT&leg2=from:EYW,to:ORD,departure:15/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:515.70&airProductToken=AQpFCiAIxJgBEgQxNDU2GK4cIOBcKJL3-wIwi_j7AjhFQABYAQohCMSYARIEMjgxNRjgXCCEtgEo9_j7AjDm-fsCOEVAAVgBCkUKIQjEmAESBDIxNjgYhLYBIOBcKPaW_QIw_Jf9AjhFQABYAQogCMSYARIEMTEzORjgXCCuHCi2mP0CMK6Z_QI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Nov 26 - Mon, Dec 15 ORD Chicago EYW Key West CA $522 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:EYW,departure:26/11/2025TANYT&leg2=from:EYW,to:ORD,departure:15/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:521.10&airProductToken=AQpFCiAIxJgBEgQxMjQ3GK4cIOBcKN2N_gIw3Y7-AjhFQABYAQohCMSYARIEMTQ3MhjgXCCEtgEo64_-AjDXkP4COEVAAVgBCkUKIQjEmAESBDIxNjgYhLYBIOBcKK7o_wIwt-n_AjhFQABYAQogCMSYARIEMTE5ORjgXCCuHCjL6v8CMMrr_wI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Oct 24 - Tue, Nov 4 MDW Chicago EYW Key West CA $524 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MDW,to:EYW,departure:24/10/2025TANYT&leg2=from:EYW,to:MDW,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:524.00&airProductToken=AQpGCiEIxJgBEgQyNDE3GOywASDgXCjsnPsCMN-d-wI4RUAAWAEKIQjEmAESBDI4MTUY4FwghLYBKPee-wIw5p_7AjhFQAFYAQpqCiEIxJgBEgQyMTY4GIS2ASDgXCiVm_wCMJWc_AI4RUAAWAEKIQjEmAESBDI5NDAY4Fwg47QBKKCd_AIwlZ78AjhFQAFYAQoiCMSYARIENTI5OBjjtAEg7LABKMuj_AIwlKT8AjhFQAFYARIKCAEQARgBKgJETBgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Oct 27 - Tue, Nov 11 ORD Chicago EYW Key West CA $533 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:EYW,departure:27/10/2025TANYT&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:532.90&airProductToken=AQpFCiAIxJgBEgQxMjY0GK4cIOBcKIy7-wIw_7v7AjhFQABYAQohCMSYARIEMTI4MRjgXCCEtgEoz7z7AjC_vfsCOEVAAVgBCkUKIQjEmAESBDIxNjgYhLYBIOBcKPbp_AIw_Or8AjhFQABYAQogCMSYARIEMTEzORjgXCCuHCi26_wCMK7s_AI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Nov 26 - Sun, Dec 14 ORD Chicago EYW Key West CA $540 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:EYW,departure:26/11/2025TANYT&leg2=from:EYW,to:ORD,departure:14/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:539.40&airProductToken=AQpFCiAIxJgBEgQxMjQ3GK4cIOBcKN2N_gIw3Y7-AjhFQABYAQohCMSYARIEMTQ3MhjgXCCEtgEo64_-AjDXkP4COEVAAVgBCkUKIQjEmAESBDIxNjgYhLYBIOBcKI7d_wIwl97_AjhFQABYAQogCMSYARIEMTE5ORjgXCCuHCir3_8CMKrg_wI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![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 $560 Roundtrip found 6 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:559.80&airProductToken=AQpCCh4IwYIBEgM1MjMYrhwgQyi76PsCMKzp-wI4T0AAWAEKIAjBggESBDI3MjAYQyCEtgEo5-n7AjCa6_sCOE9AAVgBCkQKIQjBggESBDQwNjQYhLYBIIwCKNXq_AIwiOv8AjhOQABYAQofCMGCARIDODQyGIwCIK4cKNvr_AIwre38AjhOQAFYARIKCAEQARgBKgJBQRgBIgQIARABKAgoBDAB) ## Find the cheapest month to fly from Chicago (CHI) to Key West (EYW) ### January is typically the cheapest month to fly From CA $291 - CA $665 per traveller. ## Alternative airports near Key West Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.ca/Flights-Search?leg1=from:MDW,to:EYW,departure:21/10/2025TANYT&leg2=from:EYW,to:MDW,departure:07/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) EYW Key West Intl. CheapestClosest 8 min [Flights from CA $374](https://www.expedia.ca/Flights-Search?leg1=from:MDW,to:EYW,departure:21/10/2025TANYT&leg2=from:EYW,to:MDW,departure:07/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Travel information | Origin airport | Midway Intl. | | --- | --- | | Destination airport | Key West Intl. | | Roundtrip price | CA $374 | | Distance | 1982 km | ## Book with confidence ### Illinois to Key West Flights **The easy way to book your flights from Chicago to Key West**  With Expedia, it’s simple to find and book flights to Key West from Chicago whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to Key West Intl., too.   Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Chicago to Key West today, tomorrow, or this week.   **Save dollars with cheap flights from CHI-All Airports, CHI to Key West Intl., EYW**  Sort your search results by price to find great deals on your flight from Chicago to Key West—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Key West from Chicago currently is just CA $374 rising to CA $560.   Here are more money-saving tips:  - Fly in October when flight prices are normally at their lowest  - Book about a month to 6 weeks before you travel for the best prices to Key West   - Avoid peak season and weekends when flights can cost more - Early morning and late-night flights are sometimes cheaper, so try varying your travel times  - One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free!  **Reasons to choose Expedia for your flight to Key West from Chicago**  Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Key West with Expedia today. ## Explore a world of travel with Expedia - Flights - [Flights from Hollister to Key West](https://www.expedia.ca/lp/flights/10189/1187/hollister-to-key-west) - [Flights from Davenport to Key West](https://www.expedia.ca/lp/flights/10445/1187/davenport-to-key-west) - [Flights from Kitchener to Key West](https://www.expedia.ca/lp/flights/10579/1187/kitchener-to-key-west) - [Flights from New Bedford to Key West](https://www.expedia.ca/lp/flights/1180/1187/new-bedford-to-key-west) - [Flights from Crown Point to Key West](https://www.expedia.ca/lp/flights/11941/1187/crown-point-to-key-west) - [Flights from Gillette to Key West](https://www.expedia.ca/lp/flights/1289/1187/gillette-to-key-west) - [Flights from Galveston to Key West](https://www.expedia.ca/lp/flights/1341/1187/galveston-to-key-west) - [Flights from Great Falls to Key West](https://www.expedia.ca/lp/flights/1392/1187/great-falls-to-key-west) - [Flights from Chos Malal to Key West](https://www.expedia.ca/lp/flights/1501/1187/chos-malal-to-key-west) - 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St. Paul to Key West](https://www.expedia.ca/lp/flights/178287/1187/minneapolis-st-paul-to-key-west) - [Flights from Montreal to Key West](https://www.expedia.ca/lp/flights/178288/1187/montreal-to-key-west) - [Flights from Ottawa to Key West](https://www.expedia.ca/lp/flights/178296/1187/ottawa-to-key-west) - [Flights from Phoenix to Key West](https://www.expedia.ca/lp/flights/178298/1187/phoenix-to-key-west) - [Flights from St. Petersburg - Clearwater to Key West](https://www.expedia.ca/lp/flights/178310/1187/st-petersburg-clearwater-to-key-west) - [Flights from Toronto to Key West](https://www.expedia.ca/lp/flights/178314/1187/toronto-to-key-west) - [Flights from Vancouver to Stock Island](https://www.expedia.ca/lp/flights/178315/180166/vancouver-to-stock-island) - [Flights from Edmonton to Key West](https://www.expedia.ca/lp/flights/180002/1187/edmonton-to-key-west) - [Flights from Québec City to Key West](https://www.expedia.ca/lp/flights/180017/1187/quebec-city-to-key-west) - [Flights from Sao Paulo to Fleming Key](https://www.expedia.ca/lp/flights/180023/180162/sao-paulo-to-fleming-key) - 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