Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Sitka to Chicago from $650

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
1 adult, Economy, 0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Sitka to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Alaska Airlines Logo
1:40 pm - 11:59 pm
SIT
-
ORD
7h 19m
1 stop
Alaska Airlines Logo
3:09 pm - 10:06 am
ORD
-
SIT
21h 57m
3 stops
$650Alaska Airlines
Tue, Aug 25 - Sat, Aug 29
Alaska Airlines Logo
1:40 pm - 1:54 pm
SIT
-
ORD
21h 14m
2 stops
Alaska Airlines Logo
6:00 am - 10:59 pm
ORD
-
SIT
19h 59m
3 stops
$655Alaska Airlines
Tue, Aug 25 - Sat, Aug 29
Alaska Airlines Logo
1:40 pm - 11:59 pm
SIT
-
ORD
7h 19m
1 stop
Alaska Airlines Logo
3:09 pm - 10:59 pm
ORD
-
SIT
10h 50m
3 stops
$690Alaska Airlines
Tue, Aug 25 - Sat, Aug 29
Alaska Airlines Logo
10:57 am - 7:00 am
SIT
-
ORD
17h 03m
2 stops
Alaska Airlines Logo
3:09 pm - 10:06 am
ORD
-
SIT
21h 57m
3 stops
$705Alaska Airlines
Tue, Aug 25 - Sat, Aug 29
Alaska Airlines Logo
11:22 am - 6:39 am
SIT
-
ORD
16h 17m
2 stops
Alaska Airlines Logo
6:00 am - 10:59 pm
ORD
-
SIT
19h 59m
3 stops
$744Alaska Airlines
Tue, Mar 31 - Sat, Apr 4
Alaska Airlines Logo
11:22 am - 6:39 am
SIT
-
ORD
16h 17m
2 stops
Alaska Airlines Logo
6:00 am - 6:18 pm
ORD
-
SIT
39h 18m
2 stops
$746Alaska Airlines
Wed, Apr 1 - Sun, Apr 5
Alaska Airlines Logo
6:00 am - 11:59 pm
SIT
-
ORD
14h 59m
3 stops
Alaska Airlines Logo
8:00 am - 10:59 pm
ORD
-
SIT
17h 59m
3 stops
$812Alaska Airlines
Wed, Apr 1 - Sun, Apr 5
Alaska Airlines Logo
11:22 am - 11:59 pm
SIT
-
ORD
9h 37m
1 stop
Alaska Airlines Logo
6:00 am - 10:59 pm
ORD
-
SIT
19h 59m
2 stops
$834Alaska Airlines
Wed, Apr 1 - Sun, Apr 5
Alaska Airlines Logo
7:08 pm - 12:08 pm
SIT
-
ORD
14h 00m
3 stops
Alaska Airlines Logo
3:09 pm - 10:59 pm
ORD
-
SIT
10h 50m
3 stops
$916Alaska Airlines
Tue, Aug 25 - Sat, Aug 29
Alaska Airlines Logo
7:08 pm - 12:08 pm
SIT
-
ORD
14h 00m
3 stops
Alaska Airlines Logo
3:09 pm - 10:59 pm
ORD
-
SIT
10h 50m
3 stops
$923Alaska Airlines
Tue, Aug 25 - Sat, Aug 29

Alaska Airlines flights from Sitka to Chicago

Our best Alaska Airlines deals on Sitka to Chicago flight tickets
Alaska Airlines
Aug 25
SIT1:40 pmSitka
7h 19m
1 stop
ORD11:59 pmChicago O'Hare Intl
Aug 29
ORD3:09 pmChicago O'Hare Intl
21h 57m
3 stops
SIT10:06 amSitka
$650
Alaska Airlines
Jun 30
SIT2:09 pmSitka
11h 53m
2 stops
ORD5:02 amChicago O'Hare Intl
Jul 3
ORD8:05 pmChicago O'Hare Intl
25h 28m
2 stops
SIT6:33 pmSitka
$655
Alaska Airlines
Jun 30
SIT11:39 amSitka
14h 23m
3 stops
ORD5:02 amChicago O'Hare Intl
Jul 3
ORD8:05 pmChicago O'Hare Intl
25h 28m
2 stops
SIT6:33 pmSitka
$656

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 March 20, 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

Tue 8/25

1:40 pm-11:59 pm

1 stop7h 19m

Chicago O'Hare Intl

Sat 8/29

3:09 pm-10:06 am

3 stops21h 57m

$650

SitkaChicago

SIT - ORD

SITORD

Sitka

Tue 8/25

1:40 pm-1:54 pm

2 stops21h 14m

Chicago O'Hare Intl

Sat 8/29

6:00 am-10:59 pm

3 stops19h 59m

$655
Quickest round-trip

SitkaChicago

SIT - ORD

SITORD

Sitka

Tue 8/25

1:40 pm-11:59 pm

1 stop7h 19m

Chicago O'Hare Intl

Sat 8/29

3:09 pm-10:59 pm

3 stops10h 50m

$690

SitkaChicago

SIT - ORD

SITORD

Sitka

Tue 8/25

10:57 am-7:00 am

2 stops17h 03m

Chicago O'Hare Intl

Sat 8/29

3:09 pm-10:06 am

3 stops21h 57m

$705

SitkaChicago

SIT - ORD

SITORD

Sitka

Tue 3/31

11:22 am-6:39 am

2 stops16h 17m

Chicago O'Hare Intl

Sat 4/4

6:00 am-10:59 pm

3 stops19h 59m

$744

SitkaChicago

SIT - ORD

SITORD

Sitka

Wed 4/1

11:22 am-6:39 am

2 stops16h 17m

Chicago O'Hare Intl

Sun 4/5

6:00 am-6:18 pm

2 stops39h 18m

$746

SitkaChicago

SIT - ORD

SITORD

Sitka

Wed 4/1

6:00 am-11:59 pm

3 stops14h 59m

Chicago O'Hare Intl

Sun 4/5

8:00 am-10:59 pm

3 stops17h 59m

$812

SitkaChicago

SIT - ORD

SITORD

Sitka

Wed 4/1

11:22 am-11:59 pm

1 stop9h 37m

Chicago O'Hare Intl

Sun 4/5

6:00 am-10:59 pm

2 stops19h 59m

$834

SitkaChicago

SIT - ORD

SITORD

Sitka

Tue 8/25

7:08 pm-12:08 pm

3 stops14h 00m

Chicago O'Hare Intl

Sat 8/29

3:09 pm-10:59 pm

3 stops10h 50m

$916

SitkaChicago

SIT - ORD

SITORD

Sitka

Tue 8/25

7:08 pm-12:08 pm

3 stops14h 00m

Chicago O'Hare Intl

Sat 8/29

3:09 pm-10:59 pm

3 stops10h 50m

$923

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 15% 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

7h 19m

Direct flights

None
The fastest flight from Sitka to Chicago takes 7h 19m
There are no direct flights from Sitka to Chicago. There are no popular flight routes from Sitka to Chicago.
Search flight deals

  • 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 7h 19m.

  • 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
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
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.

An easier way to manage your Chicago 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sun 4/19
Sun 4/26
By creating a price alert you accept our terms of use and privacy policy.

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