What is the cheapest airline that flies from Chicago to Sitka?

Alaska Airlines is the most popular carrier operating from Chicago to Sitka

When did momondo last update prices for flights from Chicago to Sitka Airport?

Prices for flights from Chicago to Sitka Airport refresh daily.

How old do you have to be to fly from Chicago to Sitka Airport?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Sitka Airport.

What documentation or ID do you need to fly to Sitka Airport?

The travel and health documents required for your trip to Sitka Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Sitka Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$356 Cheap Flights from Chicago to Sitka in 2025/26

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Find the cheapest flights from Chicago to Sitka

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:29 pm - 6:29 pmORD-SIT

28h 00m2 stops

11:26 am - 11:56 pmSIT-ORD

9h 30m1 stop

$601Alaska Airlines

Find Deal

Thu, Mar 5 - Mon, Mar 9

6:00 am - 10:59 pmORD-SIT

19h 59m3 stops

6:00 am - 11:59 pmSIT-ORD

14h 59m3 stops

$717Alaska Airlines

Find Deal

Mon, Dec 8 - Tue, Dec 9

10:00 am - 6:30 pmORD-SIT

11h 30m2 stops

6:00 am - 10:30 pmSIT-ORD

13h 30m3 stops

$718Alaska Airlines

Find Deal

Mon, Dec 8 - Tue, Dec 9

8:00 am - 6:30 pmORD-SIT

13h 30m2 stops

11:25 am - 2:39 pmSIT-ORD

24h 14m2 stops

$724Alaska Airlines

Find Deal

Mon, Dec 8 - Tue, Dec 9

10:00 am - 10:59 pmORD-SIT

15h 59m3 stops

11:25 am - 6:21 amSIT-ORD

39h 56m2 stops

$802Alaska Airlines

Find Deal

Tue, Dec 9 - Sat, Dec 13

10:00 am - 10:59 pmORD-SIT

15h 59m2 stops

7:18 pm - 6:21 amSIT-ORD

32h 03m2 stops

$803Alaska Airlines

Find Deal

Tue, Dec 9 - Sat, Dec 13

6:00 am - 10:59 pmORD-SIT

19h 59m3 stops

6:00 am - 11:59 pmSIT-ORD

14h 59m3 stops

$837Alaska Airlines

Find Deal

Mon, Dec 8 - Tue, Dec 9

6:00 am - 6:30 pmORD-SIT

15h 30m2 stops

6:00 am - 10:30 pmSIT-ORD

13h 30m3 stops

$838Alaska Airlines

Find Deal

Mon, Dec 8 - Tue, Dec 9

10:00 am - 6:30 pmORD-SIT

11h 30m2 stops

11:25 am - 2:39 pmSIT-ORD

24h 14m2 stops

$844Alaska Airlines

Find Deal

Mon, Dec 8 - Tue, Dec 9

3:05 pm - 6:30 pmORD-SIT

30h 25m3 stops

7:18 pm - 6:21 amSIT-ORD

32h 03m3 stops

$848Alaska Airlines

Find Deal

Tue, Dec 9 - Sat, Dec 13

Alaska Airlines flights from Chicago to Sitka

Our best Alaska Airlines deals on Chicago to Sitka flight tickets

Alaska Airlines

Mar 5

ORD1:00 pmChicago O'Hare Intl

12h 59m

3 stops

SIT10:59 pmSitka

Mar 9

SIT6:00 amSitka

14h 56m

3 stops

ORD11:56 pmChicago O'Hare Intl

$601

Find similar

Alaska Airlines

Dec 8

ORD6:00 amChicago O'Hare Intl

19h 59m

3 stops

SIT10:59 pmSitka

Dec 9

SIT6:00 amSitka

14h 59m

3 stops

ORD11:59 pmChicago O'Hare Intl

$717

Find similar

Alaska Airlines

Dec 8

ORD10:00 amChicago O'Hare Intl

11h 30m

2 stops

SIT6:30 pmSitka

Dec 9

SIT6:00 amSitka

13h 30m

3 stops

ORD10:30 pmChicago O'Hare Intl

$718

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Thu 3/5

5:29 pm-6:29 pm

2 stops28h 00m

Sitka

Mon 3/9

11:26 am-11:56 pm

1 stop9h 30m

$601

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Mon 12/8

6:00 am-10:59 pm

3 stops19h 59m

Sitka

Tue 12/9

6:00 am-11:59 pm

3 stops14h 59m

$717

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Mon 12/8

10:00 am-6:30 pm

2 stops11h 30m

Sitka

Tue 12/9

6:00 am-10:30 pm

3 stops13h 30m

$718

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Mon 12/8

8:00 am-6:30 pm

2 stops13h 30m

Sitka

Tue 12/9

11:25 am-2:39 pm

2 stops24h 14m

$724

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Tue 12/9

10:00 am-10:59 pm

3 stops15h 59m

Sitka

Sat 12/13

11:25 am-6:21 am

2 stops39h 56m

$802

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Tue 12/9

10:00 am-10:59 pm

2 stops15h 59m

Sitka

Sat 12/13

7:18 pm-6:21 am

2 stops32h 03m

$803

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Mon 12/8

6:00 am-10:59 pm

3 stops19h 59m

Sitka

Tue 12/9

6:00 am-11:59 pm

3 stops14h 59m

$837

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Mon 12/8

6:00 am-6:30 pm

2 stops15h 30m

Sitka

Tue 12/9

6:00 am-10:30 pm

3 stops13h 30m

$838

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Mon 12/8

10:00 am-6:30 pm

2 stops11h 30m

Sitka

Tue 12/9

11:25 am-2:39 pm

2 stops24h 14m

$844

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Tue 12/9

3:05 pm-6:30 pm

3 stops30h 25m

Sitka

Sat 12/13

7:18 pm-6:21 am

3 stops32h 03m

$848

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to Sitka

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest day to depart on your flight to Sitka?

On average, the least expensive day to fly to Sitka from Chicago is on a Saturday. momondo users have found tickets for Saturday departures for as low as $505. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Thursday as prices are generally higher than usual. According to our data, the average ticket price to Sitka on Thursday is $587.

What is the cheapest time of day to depart on your flight to Sitka?

According to our data, the cheapest time of day to fly to Sitka is at noon. momondo users have found flights departing from Chicago to Sitka at noon for as low as $566. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights in the morning are often more expensive with an average ticket price of $629.

When to book flights from Chicago to Sitka

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Sitka according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago to Sitka (CHI to SIT) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Sitka

Fastest flight time	18h 37m
Direct flights	None

The fastest flight from Chicago to Sitka takes 18h 37m

There are no direct flights from Chicago to Sitka. There are no popular flight routes from Chicago to Sitka.

Search flight deals

How far is Chicago to Sitka by plane?
There are 2321.6 mi between Chicago and Sitka. In terms of flight time, this usually takes a little over 11h 30m.
When did momondo last update prices for flights from Chicago to Sitka Airport?
Prices for flights from Chicago to Sitka Airport refresh daily.
How old do you have to be to fly from Chicago to Sitka Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Sitka Airport.
What documentation or ID do you need to fly to Sitka Airport?
The travel and health documents required for your trip to Sitka Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Sitka Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular airline from Chicago to Sitka?
Based on momondo bookings for flights between Chicago and Sitka, the leading airline is Alaska Airlines, making up 100% of the total bookings.

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Sitka?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Sitka for you.

Can I find flights from Chicago to Sitka with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Sitka from Chicago with this policy.

How can momondo help me find flights from Chicago to Sitka?

Once you have performed a search for Chicago to Sitka flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Sitka right now. Can momondo alert me if prices change?

Price alerts on flights to Sitka from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.