Cheap flights from Sitka to Chicago from $509

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 9/4. 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 (SIT-CHI)

Cheap round-trip flights

 Logo
11:00 am - 12:03 amSIT-ORD
10h 03m2 stops
 Logo
6:20 am - 6:27 pmORD-SIT
15h 07m2 stops
Thu, Sep 4 - Wed, Sep 10
 Logo
11:00 am - 12:03 amSIT-ORD
10h 03m2 stops
 Logo
1:01 pm - 10:59 pmORD-SIT
12h 58m3 stops
Thu, Sep 4 - Wed, Sep 10
Hawaiian Airlines Logo
1:49 pm - 12:03 amSIT-ORD
7h 14m1 stop
Hawaiian Airlines Logo
6:20 am - 12:53 pmORD-SIT
9h 33m1 stop
$554Hawaiian Airlines
Find Deal
Thu, Sep 4 - Wed, Sep 10

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 August 6, 2025.
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

SitkaChicago

SIT - ORD

SITORD

Sitka

Thu 9/4

11:00 am-12:03 am

2 stops10h 03m

Chicago O'Hare Intl

Wed 9/10

6:20 am-6:27 pm

2 stops15h 07m

$509

SitkaChicago

SIT - ORD

SITORD

Sitka

Thu 9/4

11:00 am-12:03 am

2 stops10h 03m

Chicago O'Hare Intl

Wed 9/10

1:01 pm-10:59 pm

3 stops12h 58m

$552

SitkaChicago

SIT - ORD

SITORD

Sitka

Thu 9/4

1:49 pm-12:03 am

1 stop7h 14m

Chicago O'Hare Intl

Wed 9/10

6:20 am-12:53 pm

1 stop9h 33m

$554

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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

Best Price Found

$509

Fastest flight time

7h 14m

Direct flights

None

Airports in Chicago

1 airport
The best flight deal from Sitka to Chicago found on momondo in the last 72 hours is $509
The fastest flight from Sitka to Chicago takes 7h 14m
There are no direct flights from Sitka to Chicago. Popular non-direct route for this connection is Sitka Airport - Chicago O'Hare Intl Airport.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
  • 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 14m.

  • 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.

  • How do I get Price Alerts for flights from Sitka to Chicago?

    You can take advantage of momondo’s Price Alerts by first searching for your flights to Sitka from Chicago. Flight offers will be shown to you in real-time. From there you can create a Price Alert by using our on-site widget.

  • How can I save money on flights from Sitka to Chicago with momondo?

    Leverage our AI within our “Price Forecast” tool, which predicts if it’s better to book now or wait until prices decrease. You can strategically pick the best days to fly and save money on your trip by using our “Price Calendar” tool. “Explore” shows an overview of how much it costs to fly to anywhere from a selected city or airport. Our “Discover” content is a great option for travel inspiration and money-saving tips, while “Price Alerts” will update you when prices change, so you can book when fares are right.

  • How does momondo find its flight prices?

    We compare prices from 700+ competitors to help you find the price that works best for you. momondo operates in over 30 international markets, bringing you access to a wide range of fares and deals. Search for your travel using momondo for a diverse range of options from airlines and OTAs.

Traveling to a place near Chicago?

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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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1 adult
Mon 8/11
Mon 8/18

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