Title: Chicago to Sitka cheap flights from $333 (ORD to SIT) - Expedia.com # $333 Cheap Flights from Chicago (ORD) to Sitka (SIT) [View $333 flight on Sat, Aug 22, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:ORD,to:SIT,departure:8/22/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:332.60&airProductToken=AQqUAQovCMGmARIDMzQzGK4cIJIBKJTflQMwq-GVAzhRQABYAWoETUFJTnIIUUgyT0FTTU4KLwjBpgESAjY5GJIBIKmjASj_5ZUDMOrnlQM4UUABWAFqBE1BSU5yCFFIMk9BU01OCjAIwaYBEgI3MBipowEgkpoBKJfolQMww-iVAzhRQAFYAWoETUFJTnIIUUgyT0FTTU4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAN) ## Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Sitka, AK (SIT) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:SIT,departure:4/13/2026TANYT&leg2=from:SIT,to:ORD,departure:4/20/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![](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\* - ![](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\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our OneKeyCash [Learn about One Key](https://www.expedia.com/welcome-one-key) ## Cheap Flights from Chicago to Sitka (ORD-SIT) Prices were available within the past 7 days and start at $333 for one-way flights and $515 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, May 12 - Tue, May 19 ORD Chicago SIT Sitka $515 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIT,departure:5/12/2026TANYT&leg2=from:SIT,to:ORD,departure:5/19/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:514.50&airProductToken=AQpiCi8IwaYBEgM1ODcYrhwgkgEozOSMAzDk5owDOE9AAFgBagRNQUlOcghPSDJZWFVNTgovCMGmARICOTEYkgEgkpoBKN_rjAMw8uyMAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4KlgEKMAjBpgESAzMwMxiSmgEgkgEovreNAzDUuI0DOE9AAFgBagRNQUlOcghPSDJZWFVNTgowCMGmARIEMTM2ORiSASCSaCi5uo0DMOO7jQM4T0ABWAFqBE1BSU5yCE9IMllYVU1OCjAIwaYBEgQxNDk1GJJoIK4cKIi_jQMwhsGNAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAN) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, Apr 25 - Sat, May 2 ORD Chicago SIT Sitka $518 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIT,departure:4/25/2026TANYT&leg2=from:SIT,to:ORD,departure:5/2/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:517.02&airProductToken=AQqUAQovCMGmARIDMzI5GK4cIJIBKKyriwMwxa2LAzhPQABYAWoETUFJTnIIT0gyWVhVTU4KLwjBpgESAjYxGJIBIKmjASiPsYsDMKyyiwM4T0ABWAFqBE1BSU5yCE9IMllYVU1OCjAIwaYBEgI3MBipowEgkpoBKNa4iwMwg7mLAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4KkgEKLwjBpgESAjYyGJKaASDqbCiD94sDMLr3iwM4T0AAWAFqBE1BSU5yCE9IMllYVU1OCi4IwaYBEgI2NBjqbCCSASjv-YsDMOX6iwM4T0ABWAFqBE1BSU5yCE9IMllYVU1OCi8IwaYBEgMzMjgYkgEgrhwo4fyLAzDc_osDOE9AAVgBagRNQUlOcghPSDJZWFVNThIKCAEQARgBKgJBUxgBIgQIARABKAIoAygEMA0) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, May 12 - Tue, May 19 ORD Chicago SIT Sitka $520 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIT,departure:5/12/2026TANYT&leg2=from:SIT,to:ORD,departure:5/19/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:519.80&airProductToken=AQqQAQouCMGmARIEMTQ2NhiuHCCSaCib6owDMLbsjAM4T0AAWAFqAk1BcghPSDJZWFVNTgouCMGmARIEMTUyMhiSaCCSASj774wDML3xjAM4T0ABWAFqAk1BcghPSDJZWFVNTgouCMGmARIDMzAzGJIBIJKaASiy8owDMMbzjAM4T0ABWAFqAk1BcghPSDJZWFVNTgqPAQotCMGmARICNjIYkpoBIJIBKIm2jQMw5LeNAzhPQABYAWoCTUFyCE9IMllYVU1OCi4IwaYBEgQxMzY5GJIBIJJoKLm6jQMw47uNAzhPQAFYAWoCTUFyCE9IMllYVU1OCi4IwaYBEgQxNDk1GJJoIK4cKIi_jQMwhsGNAzhPQAFYAWoCTUFyCE9IMllYVU1OEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, May 12 - Tue, May 19 ORD Chicago SIT Sitka $521 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIT,departure:5/12/2026TANYT&leg2=from:SIT,to:ORD,departure:5/19/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:520.52&airProductToken=AQpiCi8IwaYBEgM3MTUYrhwgkgEo1OOMAzDk5YwDOE9AAFgBagRNQUlOcghPSDJZWFVNTgovCMGmARICOTEYkgEgkpoBKN_rjAMw8uyMAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4KlgEKMAjBpgESAzMwMxiSmgEgkgEovreNAzDUuI0DOE9AAFgBagRNQUlOcghPSDJZWFVNTgowCMGmARIEMTM2ORiSASCSaCi5uo0DMOO7jQM4T0ABWAFqBE1BSU5yCE9IMllYVU1OCjAIwaYBEgQxNDk1GJJoIK4cKIi_jQMwhsGNAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAN) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, Apr 25 - Sat, May 2 ORD Chicago SIT Sitka $524 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIT,departure:4/25/2026TANYT&leg2=from:SIT,to:ORD,departure:5/2/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:523.04&airProductToken=AQqUAQovCMGmARIDMzI5GK4cIJIBKKyriwMwxa2LAzhPQABYAWoETUFJTnIIT0gyWVhVTU4KLwjBpgESAjYxGJIBIKmjASiPsYsDMKyyiwM4T0ABWAFqBE1BSU5yCE9IMllYVU1OCjAIwaYBEgI3MBipowEgkpoBKNa4iwMwg7mLAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4KkgEKLwjBpgESAjYyGJKaASDqbCiD94sDMLr3iwM4T0AAWAFqBE1BSU5yCE9IMllYVU1OCi4IwaYBEgI2NBjqbCCSASjv-YsDMOX6iwM4T0ABWAFqBE1BSU5yCE9IMllYVU1OCi8IwaYBEgM0MjkYkgEgrhwovIGMAzDEg4wDOE9AAVgBagRNQUlOcghPSDJZWFVNThIKCAEQARgBKgJBUxgBIgQIARABKAIoAygEMA0) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, May 12 - Tue, May 19 ORD Chicago SIT Sitka $570 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIT,departure:5/12/2026TANYT&leg2=from:SIT,to:ORD,departure:5/19/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:569.20&airProductToken=AQpiCi8IwaYBEgM1ODcYrhwgkgEozOSMAzDk5owDOE9AAFgBagRNQUlOcghPSDJZWFVNTgovCMGmARICOTEYkgEgkpoBKN_rjAMw8uyMAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4KkwEKLwjBpgESAjYyGJKaASDqbCiJto0DMMK2jQM4UUAAWAFqBE1BSU5yCFFIMllYVU1OCi8IwaYBEgM1NjUY6mwgkgEoyLeNAzDAuI0DOFFAAVgBagRNQUlOcghRSDJZWFVNTgovCMGmARIDNTM4GJIBIK4cKOq4jQMw67qNAzhRQAFYAWoETUFJTnIIUUgyWVhVTU4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAN) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, May 12 - Tue, May 19 ORD Chicago SIT Sitka $575 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIT,departure:5/12/2026TANYT&leg2=from:SIT,to:ORD,departure:5/19/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:574.50&airProductToken=AQqOAQouCMGmARIEMTQ3MBiuHCCSaCj-5IwDMJbnjAM4T0AAWAFqAk1BcghPSDJZWFVNTgotCMGmARIDNjIyGJJoIJIBKMPojAMwgOqMAzhPQAFYAWoCTUFyCE9IMllYVU1OCi0IwaYBEgI5MRiSASCSmgEo3-uMAzDy7IwDOE9AAVgBagJNQXIIT0gyWVhVTU4KXgotCMGmARICOTIYkpoBIJIBKKS0jQMws7WNAzhRQABYAWoCTUFyCFFIMllYVU1OCi0IwaYBEgM1MzgYkgEgrhwo6riNAzDruo0DOFFAAVgBagJNQXIIUUgyWVhVTU4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, Apr 25 - Sat, May 2 ORD Chicago SIT Sitka $578 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIT,departure:4/25/2026TANYT&leg2=from:SIT,to:ORD,departure:5/2/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:577.02&airProductToken=AQqUAQovCMGmARIDMzI5GK4cIJIBKKyriwMwxa2LAzhPQABYAWoETUFJTnIIT0gyWVhVTU4KLwjBpgESAjYxGJIBIKmjASiPsYsDMKyyiwM4T0ABWAFqBE1BSU5yCE9IMllYVU1OCjAIwaYBEgI3MBipowEgkpoBKNa4iwMwg7mLAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4KlAEKMAjBpgESAjczGJKaASCpowEoyPSLAzD09IsDOFFAAFgBagRNQUlOcghRSDJZWFVNTgovCMGmARICNjAYqaMBIJIBKJz1iwMwifeLAzhRQAFYAWoETUFJTnIIUUgyWVhVTU4KLwjBpgESAzQxMBiSASCuHCjM94sDMNT5iwM4UUABWAFqBE1BSU5yCFFIMllYVU1OEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwDQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, May 12 - Tue, May 19 ORD Chicago SIT Sitka $580 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIT,departure:5/12/2026TANYT&leg2=from:SIT,to:ORD,departure:5/19/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:579.80&airProductToken=AQqQAQouCMGmARIDMzI1GK4cIO-4ASjB54wDMNbpjAM4UUAAWAFqAk1BcghRSDJZWFVNTgovCMGmARIEMjExMxjvuAEgkgEo6uqMAzCi64wDOFFAAVgBagJNQXIIUUgyWVhVTU4KLQjBpgESAjkxGJIBIJKaASjf64wDMPLsjAM4UUABWAFqAk1BcghRSDJZWFVNTgqPAQotCMGmARICNjIYkpoBIJIBKIm2jQMw5LeNAzhPQABYAWoCTUFyCE9IMllYVU1OCi4IwaYBEgQxMzY5GJIBIJJoKLm6jQMw47uNAzhPQAFYAWoCTUFyCE9IMllYVU1OCi4IwaYBEgQxNDk1GJJoIK4cKIi_jQMwhsGNAzhPQAFYAWoCTUFyCE9IMllYVU1OEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, Apr 25 - Sat, May 2 ORD Chicago SIT Sitka $583 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIT,departure:4/25/2026TANYT&leg2=from:SIT,to:ORD,departure:5/2/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:582.32&airProductToken=AQqUAQovCMGmARIDMzI5GK4cIJIBKKyriwMwxa2LAzhPQABYAWoETUFJTnIIT0gyWVhVTU4KLwjBpgESAjYxGJIBIKmjASiPsYsDMKyyiwM4T0ABWAFqBE1BSU5yCE9IMllYVU1OCjAIwaYBEgI3MBipowEgkpoBKNa4iwMwg7mLAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4KlQEKMAjBpgESAjczGJKaASCpowEoyPSLAzD09IsDOFFAAFgBagRNQUlOcghRSDJZWFVNTgowCMGmARIDMzE2GKmjASCSASjI-IsDMNv5iwM4UUABWAFqBE1BSU5yCFFIMllYVU1OCi8IwaYBEgMzMjgYkgEgrhwo4fyLAzDc_osDOFFAAVgBagRNQUlOcghRSDJZWFVNThIKCAEQARgBKgJBUxgBIgQIARABKAIoAygEMA0) ## Alternative airports near Sitka Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:SIT,departure:4/13/2026TANYT&leg2=from:SIT,to:ORD,departure:4/18/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) SIT Sitka, AK CheapestClosest 4 min [Flights from $760 ](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:SIT,departure:4/13/2026TANYT&leg2=from:SIT,to:ORD,departure:4/18/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Travel information | Origin airport | O'Hare Intl. | | ------------------- | --------------- | | Destination airport | Sitka | | Airlines serving | Alaska Airlines | | Roundtrip price | $514 | | Distance | 2309 mi | \*Flight schedules are subject to change. \*Available to One Key members. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [Hotels near Isabel Miller Museum ](https://www.expedia.com/Isabel-Miller-Museum-Hotels.0-l6085517-0.Travel-Guide-Filter-Hotels) - [Sitka Hotels ](https://www.expedia.com/Sitka-Hotels.d3171.Travel-Guide-Hotels) - [Hotels near Sitka Pioneer Home ](https://www.expedia.com/Sitka-Pioneer-Home-Hotels.0-l6085513-0.Travel-Guide-Filter-Hotels) - [Hotels near Baranof Castle State Historical Site ](https://www.expedia.com/Baranof-Castle-State-Historical-Site-Hotels.0-l553248621532649924-0.Travel-Guide-Filter-Hotels) - [Portland to Sitka ](https://www.expedia.com/lp/flights/178299/3171/portland-to-sitka) - [New York to Sitka ](https://www.expedia.com/lp/flights/178293/3171/new-york-to-sitka) - [Boston to Sitka ](https://www.expedia.com/lp/flights/178239/3171/boston-to-sitka) - [San Antonio to Sitka ](https://www.expedia.com/lp/flights/178303/3171/san-antonio-to-sitka) - [Dallas to Sitka ](https://www.expedia.com/lp/flights/178253/3171/dallas-to-sitka) - [Flights to Sitka Borough ](https://www.expedia.com/Destinations-In-Sitka-Borough.d553248635975748624.Flight-Destinations) - [Flights to Sitka ](https://www.expedia.com/Cheap-Flights-To-Sitka.d3171.Travel-Guide-Flights) - [Isabel Miller Museum ](https://www.expedia.com/Isabel-Miller-Museum-Sitka.d6085517.Vacation-Attraction) - [Sheet'ka Kwaan Naa Kahidi Tribal Community House ](https://www.expedia.com/Sheetka-Kwaan-Naa-Kahidi-Tribal-Community-House-Sitka.d553248621586065691.Vacation-Attraction) - [Sitka Pioneer Home ](https://www.expedia.com/Sitka-Pioneer-Home-Sitka.d6085513.Vacation-Attraction) - [Baranof Castle State Historical Site ](https://www.expedia.com/Baranof-Castle-State-Historical-Site-Sitka.d553248621532649924.Vacation-Attraction) - [St. Michael's Cathedral ](https://www.expedia.com/St-Michaels-Cathedral-Sitka.d6085519.Vacation-Attraction) - [Visit Sitka ](https://www.expedia.com/Sitka.dx3171) - [Car rentals near Sitka ](https://www.expedia.com/Car-Rentals-In-Sitka.d3171.Car-Rental-Guide)