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Sitka

$728+ 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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SIT
nov. 29 — déc. 61
sam. 11/29
sam. 12/6
1 adult, Economy
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Find 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 octobre 30, 2025.

This Alaska Airlines deal was found by Cheapflights users on 10/29. 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.
jeu. 11/278:00 amORD - SIT
2 stops37h 32mAlaska Airlines
dim. 11/307:20 pmSIT - ORD
3 stops42h 35mAlaska Airlines
Deal found 10/29$728
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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.
jeu. 11/1310:00 amORD - SIT
3 stops15h 59mAlaska Airlines
lun. 11/1711:21 amSIT - ORD
2 stops50h 09mAlaska Airlines
Deal found 10/29$860
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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.
jeu. 11/610:00 amORD - SIT
3 stops15h 59mAlaska Airlines
dim. 11/911:21 amSIT - ORD
2 stops40h 01mAlaska Airlines
Deal found 10/28$1,168

Cheap 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 octobre 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$728
(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
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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 octobre 30, 2025.
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

jeu. 11/27

8:00 am-6:32 pm

2 stops37h 32m

Sitka

dim. 11/30

7:20 pm-4:55 pm

3 stops42h 35m

$728

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

jeu. 11/13

10:00 am-10:59 pm

3 stops15h 59m

Sitka

lun. 11/17

11:21 am-4:30 pm

2 stops50h 09m

$860

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

jeu. 11/6

6:00 am-10:59 pm

3 stops19h 59m

Sitka

dim. 11/9

11:21 am-1:54 pm

3 stops47h 33m

$1,282

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Compare providers for flights from Chicago to Sitka

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Sitka in October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Sitka flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Sitka flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.

Reviews of airlines servicing Sitka

Get insights into the airlines that provide service to Sitka. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Sitka. Reviews last updated octobre 30, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines from Chicago to Sitka to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,217 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.8

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,217 reviews
Alaska Airlines
8.0
Very good
11,217 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.8

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

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 37h 32m. 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.

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