$342 Cheap Flights from Chicago (ORD) to Sitka (SIT)

View $342 flight on Sat, Aug 30, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Sitka, AK (SIT)

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Cheap Flights from Chicago to Sitka (ORD-SIT)

Prices were available within the past 7 days and start at $342 for one-way flights and $511 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines
Wed, Sep 17 - Tue, Sep 23
ORD
Chicago
SIT
Sitka
$511 Roundtrip, just found
$511
Roundtrip
just found
Select Alaska Airlines flight, departing Wed, Sep 17 from Chicago to Sitka, returning Tue, Sep 23, priced at $511 just found
Alaska Airlines
Mon, Sep 15 - Sun, Sep 21
ORD
Chicago
SIT
Sitka
$555 Roundtrip, found 3 days ago
$555
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Mon, Sep 15 from Chicago to Sitka, returning Sun, Sep 21, priced at $555 found 3 days ago
Alaska Airlines
Wed, Sep 17 - Tue, Sep 23
ORD
Chicago
SIT
Sitka
$571 Roundtrip, just found
$571
Roundtrip
just found
Select Alaska Airlines flight, departing Wed, Sep 17 from Chicago to Sitka, returning Tue, Sep 23, priced at $571 just found
Alaska Airlines
Mon, Sep 15 - Sun, Sep 21
ORD
Chicago
SIT
Sitka
$573 Roundtrip, found 3 days ago
$573
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Mon, Sep 15 from Chicago to Sitka, returning Sun, Sep 21, priced at $573 found 3 days ago
Alaska Airlines
Sat, Sep 6 - Sat, Sep 13
ORD
Chicago
SIT
Sitka
$631 Roundtrip, found 1 day ago
$631
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Sat, Sep 6 from Chicago to Sitka, returning Sat, Sep 13, priced at $631 found 1 day ago
Alaska Airlines
Fri, Oct 10 - Wed, Oct 15
ORD
Chicago
SIT
Sitka
$663 Roundtrip, found 3 days ago
$663
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Fri, Oct 10 from Chicago to Sitka, returning Wed, Oct 15, priced at $663 found 3 days ago
Alaska Airlines
Sun, Mar 1 - Sat, Mar 7
ORD
Chicago
SIT
Sitka
$666 Roundtrip, found 1 day ago
$666
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Sun, Mar 1 from Chicago to Sitka, returning Sat, Mar 7, priced at $666 found 1 day ago
Alaska Airlines
Thu, Mar 12 - Sun, Mar 15
ORD
Chicago
SIT
Sitka
$695 Roundtrip, found 9 hours ago
$695
Roundtrip
found 9 hours ago
Select Alaska Airlines flight, departing Thu, Mar 12 from Chicago to Sitka, returning Sun, Mar 15, priced at $695 found 9 hours ago
Hawaiian Airlines
Mon, Sep 1 - Tue, Sep 2
ORD
Chicago
SIT
Sitka
$711 Roundtrip, found 13 hours ago
$711
Roundtrip
found 13 hours ago
Select Hawaiian Airlines flight, departing Mon, Sep 1 from Chicago to Sitka, returning Tue, Sep 2, priced at $711 found 13 hours ago
United
Sun, Mar 1 - Sat, Mar 7
ORD
Chicago
SIT
Sitka
$885 Roundtrip, found 1 day ago
$885
Roundtrip
found 1 day ago
Select United flight, departing Sun, Mar 1 from Chicago to Sitka, returning Sat, Mar 7, priced at $885 found 1 day ago

Alternative airports near Sitka

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Sitka, AK SIT. Cheapest and Closest option available. Average driving time to city center is 4 minutes. Flights from $989
SIT
Sitka, AK
CheapestClosest
Average driving time to city center4 min
Flights from $989
Flights from Chicago (ORD) to Sitka (SIT)
Origin airport
O'Hare Intl.
Destination airport
Sitka
Airlines serving
Alaska Airlines
Roundtrip price
$510
Distance
2309 mi

Chicago to Sitka Flights

The cheapest times to fly from Chicago to Sitka

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Sitka are during the month of September. You can find some of the cheapest flights from Chicago to Sitka with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Sitka

Sunday is one of the best days to book for cheap flights from Chicago to Sitka: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Sitka

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Sitka in 2025. You can also book with separate airlines for your outbound and return journeys, from $342 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Sitka flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Sitka airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Sitka Airport (SIT) cost?
Lock in a cheap one-way flight from $342 or cheap return flight from $511 from O'Hare Intl. Airport (ORD) to Sitka Airport (SIT) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Sitka Airport (SIT)?
Flying in September can help you save, as it's the cheapest month for flights between ORD and SIT. You'll usually find the lowest fares during the off-season.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Sitka Airport (SIT)?
Use the filter tool on Expedia to compare airlines and find the most affordable carrier that'll take you from ORD to SIT. Then, sort your results by "Price (lowest to highest)" to pick up the best deal available.
How many flights per day from O'Hare Intl. Airport (ORD) to Sitka Airport (SIT)?
You'll need to book a flight with a layover when traveling from O'Hare Intl. Airport (ORD) to Sitka Airport (SIT). There are no daily direct flights on this route. However, just filter your search to include one or two stops to discover the best option for your trip.
What day of the week has the most flights from ORD to SIT?
You'll typically find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Sitka Airport (SIT)?
To avoid potential delays on the O'Hare Intl. Airport (ORD) to Sitka Airport (SIT) route, aim to fly before 3 PM. Later departures are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Sitka Airport (SIT) last-minute?
Booking your ticket from ORD to SIT shortly before your trip is generally more expensive. But if you're flexible with your departure times and dates, you could land a cheap last-minute fare.
Is it cheaper to book an ORD to SIT flight and hotel package?
Compared with arranging hotels and flights separately, booking an ORD to SIT flight and hotel package with Expedia could result in significant savings. What's more, having everything in one easy place will take the hassle out of travel planning. Simply secure your flights and select from our extensive range of hotels, then tailor your trip with other add-ons like activities, tours and car rentals.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Sitka Airport (SIT)?
In most instances, you're able to cancel or reschedule your ORD to SIT flight. However, additional charges may apply, especially if you booked over 24 hours ago. Double-check your itinerary for the airline's fees and rules on flight changes, or if you'd like further details, visit our Customer Service portal.

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*Available to One Key members.