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Cheap flights from Sitka to Chicago from $366

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Sitka to Chicago departing on 10/1. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Sitka to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:28 pm - 5:30 pm
SIT
-
ORD
19h 02m
2 stops
Multiple Airlines Logo
10:00 am - 10:59 pm
ORD
-
SIT
15h 59m
2 stops
$719Multiple Airlines
Sat, Sep 26 - Tue, Sep 29
Alaska Airlines Logo
1:55 pm - 6:20 am
SIT
-
ORD
13h 25m
1 stop
Alaska Airlines Logo
8:00 am - 6:37 pm
ORD
-
SIT
13h 37m
2 stops
$758Alaska Airlines
Tue, Sep 22 - Sat, Sep 26
Alaska Airlines Logo
6:03 am - 6:20 am
SIT
-
ORD
21h 17m
2 stops
Alaska Airlines Logo
7:20 am - 10:59 pm
ORD
-
SIT
18h 39m
2 stops
$784Alaska Airlines
Wed, Aug 19 - Tue, Aug 25
Alaska Airlines Logo
6:03 am - 6:20 am
SIT
-
ORD
21h 17m
2 stops
Alaska Airlines Logo
9:00 am - 10:59 pm
ORD
-
SIT
16h 59m
3 stops
$821Alaska Airlines
Wed, Aug 19 - Tue, Aug 25
Alaska Airlines Logo
11:39 am - 12:03 pm
SIT
-
ORD
21h 24m
2 stops
Alaska Airlines Logo
8:20 pm - 10:40 am
ORD
-
SIT
17h 20m
2 stops
$919Alaska Airlines
Sun, Aug 2 - Thu, Aug 6
Alaska Airlines Logo
11:39 am - 12:03 pm
SIT
-
ORD
21h 24m
2 stops
Alaska Airlines Logo
7:59 pm - 6:32 pm
ORD
-
SIT
25h 33m
3 stops
$920Alaska Airlines
Sun, Aug 2 - Thu, Aug 6
Alaska Airlines Logo
11:39 am - 12:03 pm
SIT
-
ORD
21h 24m
2 stops
Alaska Airlines Logo
6:42 pm - 10:44 pm
ORD
-
SIT
31h 02m
1 stop
$925Alaska Airlines
Sun, Aug 2 - Thu, Aug 6
Alaska Airlines Logo
7:30 pm - 6:20 am
SIT
-
ORD
31h 50m
3 stops
Alaska Airlines Logo
7:59 pm - 6:32 pm
ORD
-
SIT
25h 33m
3 stops
$998Alaska Airlines
Sun, Aug 2 - Thu, Aug 6
Alaska Airlines Logo
7:28 pm - 11:59 pm
SIT
-
ORD
25h 31m
3 stops
Alaska Airlines Logo
6:00 am - 10:59 pm
ORD
-
SIT
19h 59m
3 stops
$1,018Alaska Airlines
Wed, Aug 19 - Tue, Aug 25
Alaska Airlines Logo
1:48 pm - 6:20 am
SIT
-
ORD
13h 32m
1 stop
Alaska Airlines Logo
6:00 am - 12:50 pm
ORD
-
SIT
9h 50m
1 stop
$1,190Alaska Airlines
Wed, Aug 19 - Tue, Aug 25

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Alaska Airlines flights from Sitka to Chicago

Our best Alaska Airlines deals on Sitka to Chicago flight tickets
Alaska Airlines
Sep 22
SIT1:55 pmSitka
13h 25m
1 stop
ORD6:20 amChicago O'Hare Intl
Sep 26
ORD6:00 amChicago O'Hare Intl
19h 59m
3 stops
SIT10:59 pmSitka
$758
Alaska Airlines
Aug 19
SIT6:03 amSitka
21h 17m
2 stops
ORD6:20 amChicago O'Hare Intl
Aug 25
ORD7:20 amChicago O'Hare Intl
18h 39m
2 stops
SIT10:59 pmSitka
$784
Alaska Airlines
Aug 19
SIT6:03 amSitka
14h 56m
2 stops
ORD11:59 pmChicago O'Hare Intl
Aug 25
ORD6:00 amChicago O'Hare Intl
9h 50m
1 stop
SIT12:50 pmSitka
$821

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 July 21, 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

SitkaChicago

SIT - ORD

SITORD

Sitka

Sat 9/26

7:28 pm-5:30 pm

2 stops19h 02m

Chicago O'Hare Intl

Tue 9/29

10:00 am-10:59 pm

2 stops15h 59m

$719

SitkaChicago

SIT - ORD

SITORD

Sitka

Tue 9/22

1:55 pm-6:20 am

1 stop13h 25m

Chicago O'Hare Intl

Sat 9/26

8:00 am-6:37 pm

2 stops13h 37m

$758

SitkaChicago

SIT - ORD

SITORD

Sitka

Wed 8/19

6:03 am-6:20 am

2 stops21h 17m

Chicago O'Hare Intl

Tue 8/25

7:20 am-10:59 pm

2 stops18h 39m

$784

SitkaChicago

SIT - ORD

SITORD

Sitka

Wed 8/19

6:03 am-6:20 am

2 stops21h 17m

Chicago O'Hare Intl

Tue 8/25

9:00 am-10:59 pm

3 stops16h 59m

$821

SitkaChicago

SIT - ORD

SITORD

Sitka

Sun 8/2

11:39 am-12:03 pm

2 stops21h 24m

Chicago O'Hare Intl

Thu 8/6

8:20 pm-10:40 am

2 stops17h 20m

$919

SitkaChicago

SIT - ORD

SITORD

Sitka

Sun 8/2

11:39 am-12:03 pm

2 stops21h 24m

Chicago O'Hare Intl

Thu 8/6

7:59 pm-6:32 pm

3 stops25h 33m

$920

SitkaChicago

SIT - ORD

SITORD

Sitka

Sun 8/2

11:39 am-12:03 pm

2 stops21h 24m

Chicago O'Hare Intl

Thu 8/6

6:42 pm-10:44 pm

1 stop31h 02m

$925

SitkaChicago

SIT - ORD

SITORD

Sitka

Sun 8/2

7:30 pm-6:20 am

3 stops31h 50m

Chicago O'Hare Intl

Thu 8/6

7:59 pm-6:32 pm

3 stops25h 33m

$998

SitkaChicago

SIT - ORD

SITORD

Sitka

Wed 8/19

7:28 pm-11:59 pm

3 stops25h 31m

Chicago O'Hare Intl

Tue 8/25

6:00 am-10:59 pm

3 stops19h 59m

$1,018
Quickest round-trip

SitkaChicago

SIT - ORD

SITORD

Sitka

Wed 8/19

1:48 pm-6:20 am

1 stop13h 32m

Chicago O'Hare Intl

Tue 8/25

6:00 am-12:50 pm

1 stop9h 50m

$1,190

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 resultsSorted by cheapest first
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See travel insights to Chicago from

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 2% 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

13h 25m

Direct flights

None
The fastest flight from Sitka to Chicago takes 13h 25m
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 13h 25m.

  • 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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