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$385 Cheap Flights from Chicago (ORD) to Sitka (SIT)

View $385 flight on Thu, Aug 27, 2026Opens 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 $385 for one-way flights and $549 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines
Thu, Sep 17 - Fri, Sep 18
ORD
Chicago
SIT
Sitka
$549 Roundtrip, found 3 days ago
$549
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Thu, Sep 17 from Chicago to Sitka, returning Fri, Sep 18, priced at $549 found 3 days ago
Alaska Airlines
Thu, Sep 17 - Fri, Sep 18
ORD
Chicago
SIT
Sitka
$554 Roundtrip, found 3 days ago
$554
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Thu, Sep 17 from Chicago to Sitka, returning Fri, Sep 18, priced at $554 found 3 days ago
Alaska Airlines
Thu, Sep 17 - Fri, Sep 18
ORD
Chicago
SIT
Sitka
$555 Roundtrip, found 3 days ago
$555
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Thu, Sep 17 from Chicago to Sitka, returning Fri, Sep 18, priced at $555 found 3 days ago
Alaska Airlines
Thu, Sep 17 - Fri, Sep 18
ORD
Chicago
SIT
Sitka
$559 Roundtrip, found 3 days ago
$559
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Thu, Sep 17 from Chicago to Sitka, returning Fri, Sep 18, priced at $559 found 3 days ago
Alaska Airlines
Thu, Sep 17 - Fri, Sep 18
ORD
Chicago
SIT
Sitka
$560 Roundtrip, found 3 days ago
$560
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Thu, Sep 17 from Chicago to Sitka, returning Fri, Sep 18, priced at $560 found 3 days ago
Alaska Airlines
Thu, Sep 17 - Fri, Sep 18
ORD
Chicago
SIT
Sitka
$606 Roundtrip, found 3 days ago
$606
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Thu, Sep 17 from Chicago to Sitka, returning Fri, Sep 18, priced at $606 found 3 days ago
Alaska Airlines
Thu, Sep 17 - Fri, Sep 18
ORD
Chicago
SIT
Sitka
$610 Roundtrip, found 3 days ago
$610
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Thu, Sep 17 from Chicago to Sitka, returning Fri, Sep 18, priced at $610 found 3 days ago
Alaska Airlines
Thu, Sep 17 - Fri, Sep 18
ORD
Chicago
SIT
Sitka
$612 Roundtrip, found 3 days ago
$612
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Thu, Sep 17 from Chicago to Sitka, returning Fri, Sep 18, priced at $612 found 3 days ago
Alaska Airlines
Thu, Sep 17 - Fri, Sep 18
ORD
Chicago
SIT
Sitka
$613 Roundtrip, found 3 days ago
$613
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Thu, Sep 17 from Chicago to Sitka, returning Fri, Sep 18, priced at $613 found 3 days ago
American Airlines
Mon, Sep 7 - Mon, Dec 7
ORD
Chicago
SIT
Sitka
$698 Roundtrip, found 6 days ago
$698
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Sep 7 from Chicago to Sitka, returning Mon, Dec 7, priced at $698 found 6 days ago

What you need to know for your flight from O'Hare Intl. to Sitka

Chicago (ORD) to Sitka (SIT) at a glance

Embark on a journey from Chicago O'Hare International Airport (ORD) to Sitka Airport (SIT) with a full-service carrier on this domestic long-haul route. Explore the beauty of Sitka's renowned attractions and neighborhoods while finding the itinerary that suits your travel needs. Discover essential information about flights from Chicago to Sitka and plan your adventure today.

  • Fastest flight duration: around 7h 15m in-flight, plus roughly 55 minutes layover with one stop
  • Route distance: roughly 2,300 miles (3,700 km)
  • Flights per week: around 7 departures on average
  • Typical fares (one-way): economy tickets often range from $220–$485, depending on seasonality and how far ahead you book

Flights from O'Hare International Airport (ORD) to Sitka Airport (SIT)

Based on recent traveler bookings, here are the most popular airlines flying from Chicago to Sitka, often favored for their one-stop services that typically connect through Seattle-Tacoma International Airport (SEA), with layovers lasting around 55 minutes. These options allow you to combine various factors such as price, total travel duration, and cabin class to craft the ideal itinerary for your journey.

  • Alaska Airlines: This full-service airline dominates the route, providing one-stop flights with one-way fares generally falling between $220 and $485. With an in-flight duration of 7 hours and 15 minutes, the entire travel experience, including layover time, averages around 8 hours.

Alternative routes from Chicago (ORD) to Sitka (SIT)

  • Chicago to Sitka (MDW-SIT): Midway International Airport (MDW) lies approximately 16 miles from O'Hare International Airport (ORD), offering convenient access for travelers heading to Sitka.
  • Chicago to Angoon (MDW-AGN): Midway International Airport (MDW) is roughly 16 miles from O'Hare International Airport (ORD), while Angoon Seaplane Base Airport (AGN) is located about 43 miles from Sitka Airport (SIT).
  • Chicago to Hoonah (ORD-HNH): Hoonah Airport (HNH) can be found nearly 72 miles from Sitka Airport (SIT), making it a viable option for those traveling from Chicago.

How to find the best prices for flights from Chicago (ORD) to Sitka (SIT)

Getting some of the best deals on flights from Chicago to Sitka is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are typically found when booking at least two months in advance, which aligns with when most travelers make their reservations. Morning departures between 5 a.m. and 12 p.m. not only tend to offer lower prices but are also the most popular flight times. Additionally, flying on Saturday provides both cheaper prices and is a favored travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.* Find Sitka hotel and flight deals.
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Sitka Airport from O'Hare International Airport

Sitka welcomes travelers from Chicago with a range of transport options based on price, convenience, and proximity. Here's how to reach Sitka efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Sitka, with options including free hotel shuttles and private rides, which can be arranged in advance with your hotel.
  • Car rental: Renting a car from Sitka Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Sitka Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.

Frequently asked questions

How much does a flight from Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT) cost?
You can find cheap one-way flights from $385 and cheap return flights from $549 Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT) with Expedia. One-way flights typically cost between $388 and $1628, and return flights often range between $710 and $1594. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT)?
The cheapest month to fly from ORD to SIT is September when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT)?
Enter ORD to SIT and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT)?
To find a cheap flight from Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT)?
Sort flights by "Departure (earliest)" on Expedia to find the earliest flight from ORD to SIT. To compare more early flights, use the "Early Morning" and "Morning" filters in your search.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT)?
Flights from ORD to SIT with one stop typically take around 9 hours 30 minutes, covering approximately 2,309 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT)?
Select the "Business class" and "First class" filters when looking for ORD to SIT flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
Is it cheaper to buy a plane ticket from Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT) flight and hotel package?
Securing a Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT)?
If you booked your Chicago, IL (ORD-O'Hare Intl.) to Sitka, AK (SIT) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Sitka
Airlines serving
Alaska Airlines
Roundtrip price
$548
Distance
2309 mi

Book with confidence

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 2026. You can also book with separate airlines for your outbound and return journeys, from $385 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.

 

Chicago to Sitka Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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