How long is the flight from Chicago to Sitka?

Airlines like Alaska Airlines fly from Chicago to Sitka in about 19h 39m. 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.

In terms of precipitation, rainfall in Sitka ranges from 3.5 - 14.6 inches per month. October is typically the wettest month, when rainfall can reach 14.6 in. June is typically the driest time to visit Sitka when rainfall is around 3.5 in.

If weather is an important factor for your trip to Sitka, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 53.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 32.0 F).

What is the cheapest time of day to fly from CHI to SIT?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Sitka as you normally would.

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.

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.

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.

$322+ Flights from Chicago to Sitka

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Cheap flight deals from Chicago to Sitka

Best flights from Chicago to Sitka
Discover carefully curated flight deals from Chicago to Sitka that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated diciembre 27, 2025.

vie. 6/196:20 amORD - SIT

3 stops19h 39mAlaska Airlines

sáb. 6/277:00 amSIT - ORD

2 stops19h 00mAlaska Airlines

Deal found 12/25

$650

One-way flights from Chicago to Sitka
Search for one-way flight options from Chicago to Sitka. Find affordable one-way fares based on user searches. Data last updated diciembre 27, 2025.

lun. 1/196:06 pmORD - SIT

2 stops27h 25mAlaska Airlines

Deal found 12/25

$322

Find flight deals from Chicago to Sitka

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$650 (Alaska Airlines)
One-way from	$322 (Kiwi.com)

Provider with most accurate pricing for Chicago (CHI)-Sitka flight deals.

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Provider most trusted by Cheapflights users for Chicago (CHI)-Sitka flights.

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From Chicago (CHI) to Sitka

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One-way flight from Chicago (CHI) to Sitka

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Fly from

Fly to

Route

Depart

Return

Price

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

vie. 6/19

6:20 am-10:59 pm

3 stops19h 39m

Sitka

sáb. 6/27

7:00 am-5:00 am

2 stops19h 00m

$650

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

lun. 1/19

6:06 pm-6:31 pm

2 stops27h 25m

$322

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

Compare providers for flights from Chicago to Sitka

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Sitka in December.

Provider	Price Accuracy	Trust Score*
FlightHub	Price Accuracy3 stars	Trust Score*1 star
eDreams	Price Accuracy3 stars	Trust 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

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

11,544 reviews

Reviews

1 / 20

10.0

Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.

Alaska Airlines

8.0

Very good

11,544 reviews

Alaska Airlines

8.0

Very good

11,544 reviews

Reviews

1 / 20

10.0

Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.

Related info for your journey

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 19h 39m. 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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$322+ Cheap flights from Chicago (CHI) to Sitka (SIT)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/19. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to Sitka with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Chicago to Sitka

Best flights from Chicago to SitkaDiscover carefully curated flight deals from Chicago to Sitka that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated diciembre 27, 2025.

Discover carefully curated flight deals from Chicago to Sitka that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated diciembre 27, 2025.

Find flight deals from Chicago to Sitka

Most accurate provider

Most trusted provider

Round-trip from

One-way from

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Use the filters below to find and compare flights from Chicago to Sitka that are best for you.

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 December.

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Sitka

Reviews of airlines servicing Sitka

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.

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?

How long is the flight from Chicago to Sitka?

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

How can I find direct flights from Chicago to Sitka?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Sitka

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Book with Flexibility

Travel Smart

Best flights from Chicago to Sitka
Discover carefully curated flight deals from Chicago to Sitka that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated diciembre 27, 2025.