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Cheap flights from Sitka to Chicago from $710

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Sitka to Chicago departing on 8/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Sitka to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Alaska Airlines Logo
11:23 am - 6:20 am
SIT
-
ORD
15h 57m
2 stops
Alaska Airlines Logo
9:00 am - 10:59 pm
ORD
-
SIT
16h 59m
3 stops
$710Alaska Airlines
Tue, Aug 25 - Wed, Aug 26
Alaska Airlines Logo
1:48 pm - 6:20 am
SIT
-
ORD
13h 32m
1 stop
Alaska Airlines Logo
6:54 pm - 12:50 pm
ORD
-
SIT
20h 56m
1 stop
$725Alaska Airlines
Tue, Aug 25 - Wed, Aug 26

Alaska Airlines flights from Sitka to Chicago

Our best Alaska Airlines deals on Sitka to Chicago flight tickets
Alaska Airlines
Aug 25
SIT11:23 amSitka
15h 57m
2 stops
ORD6:20 amChicago O'Hare Intl
Aug 26
ORD9:00 amChicago O'Hare Intl
16h 59m
3 stops
SIT10:59 pmSitka
$710
Alaska Airlines
Aug 25
SIT11:23 amSitka
15h 57m
2 stops
ORD6:20 amChicago O'Hare Intl
Aug 26
ORD9:00 amChicago O'Hare Intl
30h 50m
1 stop
SIT12:50 pmSitka
$725

momondo Fare Finder

 
Customize your flight search to find flights from Sitka to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated May 22, 2026.
Use the filters below to find and compare flights from Sitka to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

SitkaChicago

SIT - ORD

SITORD

Sitka

Tue 8/25

11:23 am-6:20 am

2 stops15h 57m

Chicago O'Hare Intl

Wed 8/26

9:00 am-10:59 pm

3 stops16h 59m

$710

SitkaChicago

SIT - ORD

SITORD

Sitka

Tue 8/25

1:48 pm-6:20 am

1 stop13h 32m

Chicago O'Hare Intl

Wed 8/26

6:54 pm-12:50 pm

1 stop20h 56m

$725
Cheapest one-way
Quickest one-way

SitkaChicago

SIT - ORD

SITORD

Sitka

Mon 6/22

11:39 am-6:20 am

2 stops15h 41m

$2,382

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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How to get the cheapest flight ticket from Sitka to Chicago

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

Can stopping save me money on Sitka to Chicago flights?

You could potentially save up to 10% on your flight if you consider stops on a Sitka to Chicago flight.

When to book flights from Sitka to Chicago

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

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

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

Fastest flight time

15h 57m

Direct flights

None
The fastest flight from Sitka to Chicago takes 15h 57m
There are no direct flights from Sitka to Chicago. There are no popular flight routes from Sitka to Chicago.
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Frequently asked questions about flying from Sitka to Chicago

  • How far is Sitka to Chicago by plane?

    A flight from Sitka to Chicago will travel around 2321.6 mi. A reasonable flight in good conditions will take 15h 57m.

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

    Prices for flights from Sitka Airport to Chicago are updated daily.

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Sitka Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Sitka to Chicago. momondo saves you time and could save you money on your trip.

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

Yes. All flights to Chicago from Sitka on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo provides multiple filters to help you find the best flight to Chicago from Sitka. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Sitka and alert you when they change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport