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.

$284 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.

6:00 am - 6:29 pm

ORD

SIT

15h 29m

2 stops

7:00 am - 5:57 pm

SIT

ORD

7h 57m

1 stop

$646Alaska Airlines

dom., jun. 7 - jue., jun. 11

6:00 am - 10:42 pm

ORD

SIT

19h 42m

1 stop

7:00 am - 6:44 pm

SIT

ORD

8h 44m

1 stop

$654Alaska Airlines

dom., jun. 7 - jue., jun. 11

8:00 am - 6:31 pm

ORD

SIT

37h 31m

2 stops

7:19 pm - 5:10 pm

SIT

ORD

42h 51m

3 stops

$752Alaska Airlines

vie., ene. 30 - mar., feb. 3

8:00 am - 6:31 pm

ORD

SIT

37h 31m

2 stops

11:30 am - 5:10 pm

SIT

ORD

50h 40m

2 stops

$756Alaska Airlines

vie., ene. 30 - mar., feb. 3

8:00 am - 10:59 pm

ORD

SIT

17h 59m

3 stops

6:00 am - 11:50 pm

SIT

ORD

14h 50m

3 stops

$766Alaska Airlines

vie., ene. 30 - mar., feb. 3

8:00 am - 6:31 pm

ORD

SIT

13h 31m

1 stop

11:30 am - 2:38 pm

SIT

ORD

24h 08m

1 stop

$775Alaska Airlines

vie., ene. 30 - mar., feb. 3

5:39 pm - 10:44 pm

ORD

SIT

8h 05m

1 stop

7:00 am - 5:57 pm

SIT

ORD

7h 57m

1 stop

$865Alaska Airlines

sáb., jun. 27 - lun., jul. 6

Alaska Airlines flights from Chicago to Sitka

Our best Alaska Airlines deals on Chicago to Sitka flight tickets

Alaska Airlines

Jun 7

ORD6:00 amChicago O'Hare Intl

15h 29m

2 stops

SIT6:29 pmSitka

Jun 11

SIT7:00 amSitka

7h 57m

1 stop

ORD5:57 pmChicago O'Hare Intl

$646

Alaska Airlines

Jun 7

ORD6:00 amChicago O'Hare Intl

19h 42m

1 stop

SIT10:42 pmSitka

Jun 11

SIT7:00 amSitka

8h 44m

1 stop

ORD6:44 pmChicago O'Hare Intl

$654

Alaska Airlines

Jan 30

ORD8:00 amChicago O'Hare Intl

37h 31m

2 stops

SIT6:31 pmSitka

Feb 3

SIT7:19 pmSitka

42h 51m

3 stops

ORD5:10 pmChicago O'Hare Intl

$752

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

dom. 6/7

6:00 am-6:29 pm

2 stops15h 29m

Sitka

jue. 6/11

7:00 am-5:57 pm

1 stop7h 57m

$646

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

dom. 6/7

6:00 am-10:42 pm

1 stop19h 42m

Sitka

jue. 6/11

7:00 am-6:44 pm

1 stop8h 44m

$654

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

vie. 1/30

8:00 am-6:31 pm

2 stops37h 31m

Sitka

mar. 2/3

7:19 pm-5:10 pm

3 stops42h 51m

$752

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

vie. 1/30

8:00 am-6:31 pm

2 stops37h 31m

Sitka

mar. 2/3

11:30 am-5:10 pm

2 stops50h 40m

$756

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

vie. 1/30

8:00 am-10:59 pm

3 stops17h 59m

Sitka

mar. 2/3

6:00 am-11:50 pm

3 stops14h 50m

$766

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

vie. 1/30

8:00 am-6:31 pm

1 stop13h 31m

Sitka

mar. 2/3

11:30 am-2:38 pm

1 stop24h 08m

$775

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

sáb. 6/27

5:39 pm-10:44 pm

1 stop8h 05m

Sitka

lun. 7/6

7:00 am-5:57 pm

1 stop7h 57m

$865

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

lun. 7/6

7:46 pm-10:44 pm

2 stops29h 58m

$284

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

lun. 7/6

7:40 pm-10:44 pm

1 stop30h 04m

$285

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

lun. 2/23

7:00 am-10:59 pm

3 stops18h 59m

$323

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 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	8h 05m
Direct flights	None

The fastest flight from Chicago to Sitka takes 8h 05m

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 8h 05m.
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.

An easier way to manage your Sitka trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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sáb. 2/14

sáb. 2/21

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Cheap flights from Chicago to Sitka from $284

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Sitka departing on 7/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Chicago to Sitka

Cheap round-trip flights

Cheap one-way flights

Alaska Airlines flights from Chicago to Sitka

Our best Alaska Airlines deals on Chicago to Sitka flight tickets

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

See travel insights to Sitka from

How to get the cheapest flight ticket from Chicago to Sitka

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.

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

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

When to book flights from Chicago to Sitka

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

Direct flights

How far is Chicago to Sitka by plane?

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

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

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

What is the most popular airline from Chicago to Sitka?

Why use momondo?

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

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

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

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

An easier way to manage your Sitka trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Airports servicing Alaska