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.

$299 Cheap Flights from Chicago to Sitka in 2026

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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.

7:59 pm - 12:54 pm

ORD

SIT

19h 55m

2 stops

6:00 am - 10:59 pm

SIT

ORD

13h 59m

3 stops

$581Alaska Airlines

Sat, May 23 - Wed, May 27

8:05 pm - 10:43 am

ORD

SIT

17h 38m

2 stops

7:30 pm - 6:20 am

SIT

ORD

31h 50m

3 stops

$635Alaska Airlines

Sat, Aug 1 - Sun, Aug 9

8:05 pm - 10:44 pm

ORD

SIT

29h 39m

1 stop

7:30 pm - 6:20 am

SIT

ORD

31h 50m

3 stops

$637Alaska Airlines

Sat, Aug 1 - Sun, Aug 9

7:00 am - 10:59 pm

ORD

SIT

18h 59m

3 stops

7:06 pm - 11:59 pm

SIT

ORD

25h 53m

3 stops

$684Alaska Airlines

Tue, Mar 17 - Sat, Mar 21

7:00 am - 10:59 pm

ORD

SIT

18h 59m

3 stops

11:22 am - 11:59 pm

SIT

ORD

33h 37m

2 stops

$686Alaska Airlines

Tue, Mar 17 - Sat, Mar 21

7:00 am - 10:59 pm

ORD

SIT

18h 59m

2 stops

7:06 pm - 11:59 pm

SIT

ORD

25h 53m

2 stops

$689Alaska Airlines

Tue, Mar 17 - Sat, Mar 21

5:52 pm - 10:42 pm

ORD

SIT

7h 50m

1 stop

7:00 am - 7:03 pm

SIT

ORD

9h 03m

1 stop

$698Alaska Airlines

Sat, May 23 - Wed, May 27

8:05 pm - 10:43 am

ORD

SIT

17h 38m

2 stops

2:09 pm - 6:20 am

SIT

ORD

13h 11m

1 stop

$703Alaska Airlines

Sat, Aug 1 - Sun, Aug 9

8:05 pm - 10:44 pm

ORD

SIT

29h 39m

1 stop

2:09 pm - 6:20 am

SIT

ORD

13h 11m

1 stop

$705Alaska Airlines

Sat, Aug 1 - Sun, Aug 9

5:39 pm - 10:59 pm

ORD

SIT

32h 20m

3 stops

7:30 pm - 6:20 am

SIT

ORD

31h 50m

3 stops

$761Alaska Airlines

Sat, Aug 1 - Sun, Aug 9

Alaska Airlines flights from Chicago to Sitka

Our best Alaska Airlines deals on Chicago to Sitka flight tickets

Alaska Airlines

May 23

ORD7:59 pmChicago O'Hare Intl

19h 55m

2 stops

SIT12:54 pmSitka

May 27

SIT6:00 amSitka

13h 59m

3 stops

ORD10:59 pmChicago O'Hare Intl

$581

Alaska Airlines

Aug 1

ORD8:05 pmChicago O'Hare Intl

17h 38m

2 stops

SIT10:43 amSitka

Aug 9

SIT7:30 pmSitka

31h 50m

3 stops

ORD6:20 amChicago O'Hare Intl

$635

Alaska Airlines

Aug 1

ORD8:05 pmChicago O'Hare Intl

29h 39m

1 stop

SIT10:44 pmSitka

Aug 9

SIT7:30 pmSitka

31h 50m

3 stops

ORD6:20 amChicago O'Hare Intl

$637

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Sat 5/23

7:59 pm-12:54 pm

2 stops19h 55m

Sitka

Wed 5/27

6:00 am-10:59 pm

3 stops13h 59m

$581

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Sat 8/1

8:05 pm-10:43 am

2 stops17h 38m

Sitka

Sun 8/9

7:30 pm-6:20 am

3 stops31h 50m

$635

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Sat 8/1

8:05 pm-10:44 pm

1 stop29h 39m

Sitka

Sun 8/9

7:30 pm-6:20 am

3 stops31h 50m

$637

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Tue 3/17

7:00 am-10:59 pm

3 stops18h 59m

Sitka

Sat 3/21

7:06 pm-11:59 pm

3 stops25h 53m

$684

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Tue 3/17

7:00 am-10:59 pm

3 stops18h 59m

Sitka

Sat 3/21

11:22 am-11:59 pm

2 stops33h 37m

$686

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Tue 3/17

7:00 am-10:59 pm

2 stops18h 59m

Sitka

Sat 3/21

7:06 pm-11:59 pm

2 stops25h 53m

$689

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Sat 5/23

5:52 pm-10:42 pm

1 stop7h 50m

Sitka

Wed 5/27

7:00 am-7:03 pm

1 stop9h 03m

$698

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Sat 8/1

8:05 pm-10:43 am

2 stops17h 38m

Sitka

Sun 8/9

2:09 pm-6:20 am

1 stop13h 11m

$703

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Sat 8/1

8:05 pm-10:44 pm

1 stop29h 39m

Sitka

Sun 8/9

2:09 pm-6:20 am

1 stop13h 11m

$705

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

Sat 8/1

5:39 pm-10:59 pm

3 stops32h 20m

Sitka

Sun 8/9

7:30 pm-6:20 am

3 stops31h 50m

$761

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 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

Can stopping save me money on Chicago to Sitka flights?

You could potentially save up to 14% on your flight if you consider stops on a Chicago to Sitka flight.

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 18h 37m.
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.

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.