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Sitka

$483+ Cheap flights from Chicago (CHI) to Sitka (SIT)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SIT
Mar 15 — Mar 221
Sun 3/15
Sun 3/22
1 adult, Economy
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Cheap flight deals from Chicago to Sitka

Cheapest flights from Chicago to Sitka
Explore the most affordable flight options available from Chicago to Sitka. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 13, 2026.

This Alaska Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:55 pm
ORD
-
SIT
2 stops51h 26m
Alaska Airlines
Sat 10/3110:57 am
SIT
-
ORD
2 stops17h 03m
Alaska Airlines
Deal found 2/10$483
This Alaska Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:00 am
ORD
-
SIT
2 stops15h 33m
Alaska Airlines
Sun 5/311:15 am
SIT
-
ORD
2 stops16h 25m
Alaska Airlines
Deal found 2/10$531
This Alaska Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/17:20 am
ORD
-
SIT
2 stops18h 24m
Alaska Airlines
Wed 7/811:04 am
SIT
-
ORD
2 stops16h 16m
Alaska Airlines
Deal found 2/11$581
This Alaska Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/127:00 am
ORD
-
SIT
2 stops18h 59m
Alaska Airlines
Thu 3/1911:22 am
SIT
-
ORD
1 stop16h 17m
Alaska Airlines
Deal found 2/12$630
This Alaska Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/147:20 am
ORD
-
SIT
2 stops18h 24m
Alaska Airlines
Sun 6/2111:04 am
SIT
-
ORD
2 stops16h 16m
Alaska Airlines
Deal found 2/11$635
This Alaska Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/277:00 am
ORD
-
SIT
3 stops18h 59m
Alaska Airlines
Tue 3/311:26 am
SIT
-
ORD
2 stops9h 30m
Alaska Airlines
Deal found 2/12$684

Find flight deals from Chicago to Sitka

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Sitka (SIT). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 13, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$531
(Alaska Airlines)
Provider with most accurate pricing for Chicago (CHI)-Sitka flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Sitka flights.
Search Deals
From Chicago (CHI) to Sitka
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Sitka that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 13, 2026.
Use the filters below to find and compare flights from Chicago to Sitka that are best for you.

Fly from

Chicago

Fly to

Sitka

Route

Depart

Return

Price

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Thu 4/30

6:00 am-6:33 pm

2 stops15h 33m

Sitka

Sun 5/3

11:15 am-6:40 am

2 stops16h 25m

$531

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Wed 7/1

7:20 am-10:44 pm

2 stops18h 24m

Sitka

Wed 7/8

1:45 pm-6:20 am

1 stop13h 35m

$581

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Thu 3/12

7:00 am-10:59 pm

2 stops18h 59m

Sitka

Thu 3/19

6:00 am-11:59 pm

2 stops14h 59m

$630

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Sun 6/14

7:20 am-10:44 pm

2 stops18h 24m

Sitka

Sun 6/21

11:04 am-6:20 am

2 stops16h 16m

$635

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

  • Most accurate provider: When it comes to deals on Chicago-Sitka flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Sitka flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Sitka flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Sitka flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Sitka flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Sitka

Have a flexible travel schedule? Discover the best time to fly to Sitka from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Sitka
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Sitka. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Sitka from Chicago?

    Located just 1.2 mi from the city center, Sitka is the airport most travelers will use when flying to Sitka from Chicago. Booking flights from Chicago to Sitka (SIT) should be relatively easy as there are 0 daily inbound flights from Chicago from 0 different airlines.

  • How long is the flight from Chicago to Sitka?

    Airlines like Alaska Airlines fly from Chicago to Sitka in about 15h 33m. The time it takes to get you to your destination can typically vary by up to . The distance from Chicago to Sitka is about 2307 mi.

  • Can I find deals for flights from Chicago to Sitka that include hotel bookings?

    Yes. In addition to deals on Chicago to Sitka flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Sitka?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Sitka.

  • Can I find deals for business class flights from Chicago to Sitka?

    Yes. Cheapflights offers flight deals from Chicago to Sitka by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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