Title: Chicago to Sitka cheap flights from $238 (ORD to SIT) - Expedia.com ![Sitka which includes mountains, a coastal town and a bay or harbor](https://images.trvl-media.com/place/3171/45ab516d-fea5-4cce-b2ad-994e8810db21.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by State of Alaska/Mark Kelley ![](https://images.trvl-media.com/place/3171/45ab516d-fea5-4cce-b2ad-994e8810db21.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $238 Cheap Flights from Chicago (ORD) to Sitka (SIT) [View $238 flight on Wed, Apr 29, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:ORD,to:SIT,departure:4/29/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:237.67&airProductToken=AQqUAQovCMGmARIDMzI5GK4cIJIBKKzYiwMwxdqLAzhPQABYAWoETUFJTnIIT0gyWVhVTU4KLwjBpgESAjYxGJIBIKmjASiP3osDMKzfiwM4T0ABWAFqBE1BSU5yCE9IMllYVU1OCjAIwaYBEgI3MBipowEgkpoBKNbliwMwg-aLAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAN) ## 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:3/29/2026TANYT&leg2=from:SIT,to:ORD,departure:4/5/2026TANYT&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 $238 for one-way flights and $455 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) Sat, Apr 18 - Sat, Apr 25 ORD Chicago SIT Sitka $455 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIT,departure:4/18/2026TANYT&leg2=from:SIT,to:ORD,departure:4/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:454.49&airProductToken=AQqUAQovCMGmARIDMzQ5GK4cIJIBKNTVigMw6deKAzhPQABYAWoETUFJTnIIT0gyWVhVTU4KLwjBpgESAjcxGJIBIKmjASiV2YoDMLHaigM4T0ABWAFqBE1BSU5yCE9IMllYVU1OCjAIwaYBEgI3MBipowEgkpoBKNjeigMwg9-KAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4KlAEKMAjBpgESAjY3GJKaASCpowEoiayLAzC1rIsDOE9AAFgBagRNQUlOcghPSDJZWFVNTgovCMGmARICNjAYqaMBIJIBKNyxiwMwybOLAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4KLwjBpgESAzUzOBiSASCuHCiKtosDMIu4iwM4T0ABWAFqBE1BSU5yCE9IMllYVU1OEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwDQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, Apr 29 - Tue, May 5 ORD Chicago SIT Sitka $457 Roundtrip found 2 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIT,departure:4/29/2026TANYT&leg2=from:SIT,to:ORD,departure:5/5/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:456.67&airProductToken=AQqUAQovCMGmARIDMzI5GK4cIJIBKKzYiwMwxdqLAzhPQABYAWoETUFJTnIIT0gyWVhVTU4KLwjBpgESAjYxGJIBIKmjASiP3osDMKzfiwM4T0ABWAFqBE1BSU5yCE9IMllYVU1OCjAIwaYBEgI3MBipowEgkpoBKNbliwMwg-aLAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4KkgEKLwjBpgESAjYyGJKaASDqbCjjmIwDMJqZjAM4T0AAWAFqBE1BSU5yCE9IMllYVU1OCi4IwaYBEgI2NBjqbCCSASjPm4wDMMWcjAM4T0ABWAFqBE1BSU5yCE9IMllYVU1OCi8IwaYBEgMzMjgYkgEgrhwowZ6MAzC8oIwDOE9AAVgBagRNQUlOcghPSDJZWFVNThIKCAEQARgBKgJBUxgBIgQIARABKAIoAygEMA0) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, Apr 18 - Sat, Apr 25 ORD Chicago SIT Sitka $460 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIT,departure:4/18/2026TANYT&leg2=from:SIT,to:ORD,departure:4/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:459.79&airProductToken=AQqUAQovCMGmARIDMzQ5GK4cIJIBKNTVigMw6deKAzhPQABYAWoETUFJTnIIT0gyWVhVTU4KLwjBpgESAjcxGJIBIKmjASiV2YoDMLHaigM4T0ABWAFqBE1BSU5yCE9IMllYVU1OCjAIwaYBEgI3MBipowEgkpoBKNjeigMwg9-KAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4KlAEKMAjBpgESAjczGJKaASCpowEo6KWLAzCUposDOE9AAFgBagRNQUlOcghPSDJZWFVNTgovCMGmARICNjYYqaMBIJIBKKuriwMwvqyLAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4KLwjBpgESAzMyOBiSASCuHCiBrosDMPyviwM4T0ABWAFqBE1BSU5yCE9IMllYVU1OEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwDQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, Apr 29 - Tue, May 5 ORD Chicago SIT Sitka $462 Roundtrip found 2 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIT,departure:4/29/2026TANYT&leg2=from:SIT,to:ORD,departure:5/5/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:461.97&airProductToken=AQqUAQovCMGmARIDMzI5GK4cIJIBKKzYiwMwxdqLAzhPQABYAWoETUFJTnIIT0gyWVhVTU4KLwjBpgESAjYxGJIBIKmjASiP3osDMKzfiwM4T0ABWAFqBE1BSU5yCE9IMllYVU1OCjAIwaYBEgI3MBipowEgkpoBKNbliwMwg-aLAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4KlAEKMAjBpgESAjczGJKaASCpowEoqJaMAzDUlowDOE9AAFgBagRNQUlOcghPSDJZWFVNTgovCMGmARICNjYYqaMBIJIBKOubjAMw_pyMAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4KLwjBpgESAzMyOBiSASCuHCjBnowDMLygjAM4T0ABWAFqBE1BSU5yCE9IMllYVU1OEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwDQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, Apr 18 - Sat, Apr 25 ORD Chicago SIT Sitka $520 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIT,departure:4/18/2026TANYT&leg2=from:SIT,to:ORD,departure:4/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:519.20&airProductToken=AQqUAQovCMGmARIDMzQ5GK4cIJIBKNTVigMw6deKAzhRQABYAWoETUFJTnIIUUgyWVhVTU4KLwjBpgESAjY5GJIBIKmjASjF3IoDMKjeigM4UUABWAFqBE1BSU5yCFFIMllYVU1OCjAIwaYBEgI3MBipowEgkpoBKNjeigMwg9-KAzhRQAFYAWoETUFJTnIIUUgyWVhVTU4KlAEKMAjBpgESAjY3GJKaASCpowEoiayLAzC1rIsDOE9AAFgBagRNQUlOcghPSDJZWFVNTgovCMGmARICNjAYqaMBIJIBKNyxiwMwybOLAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4KLwjBpgESAzUzOBiSASCuHCiKtosDMIu4iwM4T0ABWAFqBE1BSU5yCE9IMllYVU1OEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwDQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, Apr 18 - Sat, Apr 25 ORD Chicago SIT Sitka $523 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIT,departure:4/18/2026TANYT&leg2=from:SIT,to:ORD,departure:4/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:522.17&airProductToken=AQqUAQovCMGmARIDMzQ5GK4cIJIBKNTVigMw6deKAzhRQABYAWoETUFJTnIIUUgyWVhVTU4KLwjBpgESAjY5GJIBIKmjASjF3IoDMKjeigM4UUABWAFqBE1BSU5yCFFIMllYVU1OCjAIwaYBEgI2MhipowEgkpoBKI3kigMwuuSKAzhRQAFYAWoETUFJTnIIUUgyWVhVTU4KlAEKMAjBpgESAjY3GJKaASCpowEoiayLAzC1rIsDOE9AAFgBagRNQUlOcghPSDJZWFVNTgovCMGmARICNjAYqaMBIJIBKNyxiwMwybOLAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4KLwjBpgESAzUzOBiSASCuHCiKtosDMIu4iwM4T0ABWAFqBE1BSU5yCE9IMllYVU1OEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwDQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, Apr 18 - Sat, Apr 25 ORD Chicago SIT Sitka $525 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIT,departure:4/18/2026TANYT&leg2=from:SIT,to:ORD,departure:4/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:524.50&airProductToken=AQqUAQovCMGmARIDMzQ5GK4cIJIBKNTVigMw6deKAzhPQABYAWoETUFJTnIIT0gyWVhVTU4KLwjBpgESAjcxGJIBIKmjASiV2YoDMLHaigM4T0ABWAFqBE1BSU5yCE9IMllYVU1OCjAIwaYBEgI3MBipowEgkpoBKNjeigMwg9-KAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4KlAEKMAjBpgESAjY3GJKaASCpowEoiayLAzC1rIsDOFFAAFgBagRNQUlOcghRSDJZWFVNTgovCMGmARICNjAYqaMBIJIBKNyxiwMwybOLAzhRQAFYAWoETUFJTnIIUUgyWVhVTU4KLwjBpgESAzQxMBiSASCuHCiMtIsDMJS2iwM4UUABWAFqBE1BSU5yCFFIMllYVU1OEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwDQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, May 2 - Sat, May 9 ORD Chicago SIT Sitka $527 Roundtrip found 12 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIT,departure:5/2/2026TANYT&leg2=from:SIT,to:ORD,departure:5/9/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:526.67&airProductToken=AQqUAQovCMGmARIDMzI5GK4cIJIBKIz6iwMwpfyLAzhPQABYAWoETUFJTnIIT0gyWVhVTU4KLwjBpgESAjYxGJIBIKmjASjv_4sDMIyBjAM4T0ABWAFqBE1BSU5yCE9IMllYVU1OCjAIwaYBEgI3MBipowEgkpoBKLaHjAMw44eMAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4KlAEKMAjBpgESAjY3GJKaASCpowEoycmMAzD1yYwDOFFAAFgBagRNQUlOcghRSDJZWFVNTgovCMGmARICNjAYqaMBIJIBKJzPjAMwidGMAzhRQAFYAWoETUFJTnIIUUgyWVhVTU4KLwjBpgESAzUzOBiSASCuHCjK04wDMMvVjAM4UUABWAFqBE1BSU5yCFFIMllYVU1OEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwDQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, May 19 - Tue, May 26 ORD Chicago SIT Sitka $528 Roundtrip found 6 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIT,departure:5/19/2026TANYT&leg2=from:SIT,to:ORD,departure:5/26/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:527.50&airProductToken=AQqUAQowCMGmARIEMTQ3MBiuHCCSaCjos40DMP21jQM4T0AAWAFqBE1BSU5yCE9IMllYVU1OCi8IwaYBEgM1NzQYkmggkgEo0biNAzCQuo0DOE9AAVgBagRNQUlOcghPSDJZWFVNTgovCMGmARICOTEYkgEgkpoBKL-6jQMw0ruNAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4KYgovCMGmARICOTIYkpoBIJIBKISDjgMwk4SOAzhRQABYAWoETUFJTnIIUUgyT0FTTU4KLwjBpgESAzUzOBiSASCuHCjKh44DMMuJjgM4UUABWAFqBE1BSU5yCFFIMk9BU01OEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwDQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, Apr 29 - Tue, May 5 ORD Chicago SIT Sitka $529 Roundtrip found 2 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SIT,departure:4/29/2026TANYT&leg2=from:SIT,to:ORD,departure:5/5/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:528.58&airProductToken=AQqUAQovCMGmARIDMzI5GK4cIJIBKKzYiwMwxdqLAzhPQABYAWoETUFJTnIIT0gyWVhVTU4KLwjBpgESAjYxGJIBIKmjASiP3osDMKzfiwM4T0ABWAFqBE1BSU5yCE9IMllYVU1OCjAIwaYBEgI3MBipowEgkpoBKNbliwMwg-aLAzhPQAFYAWoETUFJTnIIT0gyWVhVTU4KkgEKLwjBpgESAjYyGJKaASDqbCjjmIwDMJqZjAM4UUAAWAFqBE1BSU5yCFFIMllYVU1OCi4IwaYBEgI2MBjqbCCSASiQo4wDMImkjAM4UUABWAFqBE1BSU5yCFFIMllYVU1OCi8IwaYBEgM0MTAYkgEgrhwozKSMAzDUpowDOFFAAVgBagRNQUlOcghRSDJZWFVNThIKCAEQARgBKgJBUxgBIgQIARABKAIoAygEMA0) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=FTG_SPRING_PROMO_) ## Frequently asked questions ### How much does a flight from Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT) cost? ### What is the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT)? ### Which airlines fly direct from Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT)? ### How do I find cheap flights from Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT)? ### What is the best time to fly from Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT)? ### What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT)? ### How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT)? ### Can you fly business or first class from Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT)? ### How do I earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT) flight with Expedia? ### Is it cheaper to buy a plane ticket from Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT) at the last minute? ### Is it cheaper to book a Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT) flight and hotel package? ### Can I cancel or change the date of my flight from Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT)? ## Travel information | Origin airport | O'Hare Intl. | | ------------------- | --------------- | | Destination airport | Sitka | | Airlines serving | Alaska Airlines | | Roundtrip price | $454 | | Distance | 2309 mi | ## Book with confidence # Chicago to Sitka Flights The cheapest times to fly from Chicago to Sitka On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Sitka are during the month of April. You can find some of the cheapest flights from Chicago to Sitka with Expedia's search tool and vast selection of airlines. The best time to book a flight from Chicago to Sitka Sunday is one of the best days to book for cheap flights from Chicago to Sitka: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance. How to find cheap round-trip tickets from Chicago to Sitka Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Sitka in 2026\. You can also book with separate airlines for your outbound and return journeys, from $238 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference\*. This is available for a small fee, and is free to One Key Gold and Platinum tier members. Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Sitka flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps. You could also save big by booking one of Expedia's [vacation packages](https://www.expedia.com/package-deals). Bundling together your Chicago to Sitka airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures. \*Terms apply. Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023\. 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