What are the cheapest airlines flying from Chicago to Sitka round-trip?

According to our current data, Alaska Airlines ($680), and Hawaiian Airlines ($701) offers the cheapest pricing from Chicago to Sitka.

What is the cheapest day to fly from Chicago to Sitka?

Travelers seeking maximum savings on their Chicago to Sitka flight should consider departing on Saturday at noon when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

What is the cheapest day to fly round-trip from Chicago to Sitka?

Flying to your destination on a Wednesday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Sitka. Check prices with Cheapflights to find a great deal for your trip.

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.

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.

$343+ Flights from Chicago to Sitka - Compare & Save Big

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1. Tell us where you want to go

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Cheap flight deals from Chicago to Sitka

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 2 stars
Round-trip from	$671 (Trip.com)
One-way from	$343 (Alaska Airlines)

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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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 May 1, 2025.

Fri 6/1312:59 amORD - SIT

2 stops12h 06mMultiple Airlines

Sat 6/211:40 pmSIT - ORD

1 stop7h 19mMultiple Airlines

Deal found 4/30

$671

Fri 6/1312:59 amORD - SIT

1 stop12h 06mAlaska Airlines

Sat 6/211:40 pmSIT - ORD

1 stop7h 19mAlaska Airlines

Deal found 4/30

$680

Sat 6/146:00 amORD - SIT

1 stop19h 44mHawaiian Airlines

Sat 6/211:40 pmSIT - ORD

1 stop7h 19mHawaiian Airlines

Deal found 4/30

$701

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 May 1, 2025.

Fri 6/1312:59 amORD - SIT

2 stops12h 06mMultiple Airlines

Sat 6/211:40 pmSIT - ORD

1 stop7h 19mMultiple Airlines

Deal found 4/30

$671

Fri 6/1312:59 amORD - SIT

2 stops12h 06mAlaska Airlines

Sat 6/2110:57 amSIT - ORD

2 stops10h 02mAlaska Airlines

Deal found 4/30

$680

Sat 6/146:00 amORD - SIT

1 stop19h 44mHawaiian Airlines

Sat 6/211:40 pmSIT - ORD

1 stop7h 19mHawaiian Airlines

Deal found 4/30

$701

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 May 1, 2025.

Sat 8/166:00 amORD - SIT

1 stop19h 44mAlaska Airlines

Deal found 5/1

$343

Sat 6/143:09 pmORD - SIT

1 stop10h 35mHawaiian Airlines

Deal found 4/30

$371

Fri 6/1312:59 amORD - SIT

2 stops12h 06mMultiple Airlines

Deal found 4/30

$547

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Fri 6/13

12:59 am-10:05 am

2 stops12h 06m

Sitka

Sat 6/21

1:40 pm-11:59 pm

1 stop7h 19m

$671

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Fri 6/13

12:59 am-10:05 am

1 stop12h 06m

Sitka

Sat 6/21

1:40 pm-11:59 pm

1 stop7h 19m

$680

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Sat 6/14

6:00 am-10:44 pm

1 stop19h 44m

Sitka

Sat 6/21

1:40 pm-11:59 pm

1 stop7h 19m

$701

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Sat 8/16

6:00 am-10:44 pm

1 stop19h 44m

$343

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Sat 6/14

3:09 pm-10:44 pm

1 stop10h 35m

$371

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Fri 6/13

12:59 am-10:05 am

2 stops12h 06m

$547

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

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

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

When flying from Chicago to Sitka, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 11% versus a flight in the morning.

Rainfall in Sitka by month

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.

Temperature in Sitka by month

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).

Reviews of airlines servicing Sitka

Alaska Airlines

8.0

Very good

9,972 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Alaska Airlines

8.0

Very good

9,972 reviews

Alaska Airlines

8.0

Very good

9,972 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Hawaiian Airlines

7.9

Good

2,409 reviews

Alaska Airlines

8.0

Very good

9,972 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.
What are the cheapest airlines flying from Chicago to Sitka round-trip?
According to our current data, Alaska Airlines ($680), and Hawaiian Airlines ($701) offers the cheapest pricing from Chicago to Sitka.
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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Alternative routes for Chicago to Sitka

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$343+ 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 8/16. 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

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Find flight deals from Chicago to Sitka

Cheapest flights from Chicago to SitkaExplore 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 May 1, 2025.

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 May 1, 2025.

Cheapflights Fare Finder

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

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

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

Find hourly flight availability from Chicago to Sitka. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 1, 2025.

Rainfall in Sitka by month

Plan your trip to Sitka by taking into account the average rainfall totals by month.

Temperature in Sitka by month

Plan your trip to Sitka by taking into account the average temperature totals by month.

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 May 1, 2025.

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?

What are the cheapest airlines flying from Chicago to Sitka round-trip?

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

See prices for flight routes from nearby airports that may be better suited for you.

100% Free

Book with Flexibility

Travel Smart

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 May 1, 2025.