What is the cheapest day to fly from Chicago to Sitka?

Travelers seeking maximum savings on their Chicago to Sitka flight should consider departing on Saturday at noon when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

In terms of precipitation, rainfall in Sitka ranges from 3.5 - 14.6 inches per month. October is typically the wettest month, when rainfall can reach 14.6 in. June is typically the driest time to visit Sitka when rainfall is around 3.5 in.

If weather is an important factor for your trip to Sitka, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 53.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 32.0 F).

What is the cheapest day to fly round-trip from Chicago to Sitka?

Flying to your destination on a Wednesday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Sitka. Check prices with Cheapflights to find a great deal for your trip.

What is the cheapest time of day to fly from CHI to SIT?

When flying from Chicago to Sitka, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 11% versus a flight in the morning.

What airport do you fly into for flights to Sitka from Chicago?

Located just 1.2 mi from the city center, Sitka is the airport most travelers will use when flying to Sitka from Chicago. Booking flights from Chicago to Sitka (SIT) should be relatively easy as there are 0 daily inbound flights from Chicago from 0 different airlines.

Can I find deals for flights from Chicago to Sitka that include hotel bookings?

Yes. In addition to deals on Chicago to Sitka flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Chicago to Sitka?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Sitka.

Can I find deals for business class flights from Chicago to Sitka?

Yes. Cheapflights offers flight deals from Chicago to Sitka by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$695+ Cheap Flights from Chicago to Sitka

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Cheap flight deals from Chicago to Sitka

Round-trip from	$695 (Alaska Airlines)

From Chicago (CHI) to Sitka

Search Deals

Find flight deals from Chicago to Sitka

Cheapest flights from Chicago to Sitka
Explore the most affordable flight options available from Chicago to Sitka. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 14, 2025.

jue. 9/111:01 pmORD - SIT

2 stops12h 58mAlaska Airlines

jue. 9/1811:00 amSIT - ORD

1 stop10h 03mAlaska Airlines

Deal found 8/12

$695

vie. 8/296:20 amORD - SIT

2 stops19h 39mAlaska Airlines

mar. 9/21:49 pmSIT - ORD

1 stop14h 14mAlaska Airlines

Deal found 8/14

$904

lun. 8/188:00 amORD - SIT

2 stops13h 20mAlaska Airlines

mié. 8/207:17 pmSIT - ORD

2 stops21h 31mAlaska Airlines

Deal found 8/14

$1,493

Best flights from Chicago to Sitka
Discover carefully curated flight deals from Chicago to Sitka that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated agosto 14, 2025.

jue. 9/111:01 pmORD - SIT

2 stops12h 58mAlaska Airlines

jue. 9/1811:00 amSIT - ORD

1 stop10h 03mAlaska Airlines

Deal found 8/12

$695

vie. 8/296:20 amORD - SIT

2 stops19h 39mAlaska Airlines

mar. 9/21:49 pmSIT - ORD

1 stop14h 14mAlaska Airlines

Deal found 8/14

$904

Last-minute flights from Chicago to Sitka
Discover last-minute flight deals from Chicago to Sitka. Data last updated agosto 14, 2025 and is based on user searches.

lun. 8/188:00 amORD - SIT

2 stops13h 20mAlaska Airlines

mié. 8/207:17 pmSIT - ORD

2 stops21h 31mAlaska Airlines

Deal found 8/14

$1,493

vie. 8/296:20 amORD - SIT

2 stops19h 39mAlaska Airlines

mar. 9/21:49 pmSIT - ORD

1 stop14h 14mAlaska Airlines

Deal found 8/14

$904

jue. 9/111:01 pmORD - SIT

2 stops12h 58mAlaska Airlines

jue. 9/1811:00 amSIT - ORD

1 stop10h 03mAlaska Airlines

Deal found 8/12

$695

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

jue. 9/11

1:01 pm-10:59 pm

2 stops12h 58m

Sitka

jue. 9/18

11:00 am-12:03 am

1 stop10h 03m

$695

ChicagoSitka

ORD - SIT

ORDSIT

Chicago O'Hare Intl

vie. 8/29

6:20 am-10:59 pm

2 stops19h 39m

Sitka

mar. 9/2

1:49 pm-7:03 am

1 stop14h 14m

$904

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Best time to book a flight from Chicago to Sitka

Have a flexible travel schedule? Discover the best time to fly to Sitka from Chicago with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Sitka

No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Sitka

Peruse reviews from past customers who have flown with Alaska Airlines from Chicago to Sitka to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Alaska Airlines

8.0

Very good

10,000 reviews

Reviews

1 / 20

8.0

Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)

Alaska Airlines

8.0

Very good

10,000 reviews

Alaska Airlines

8.0

Very good

10,000 reviews

Reviews

1 / 20

8.0

Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)

Related info for your journey

What airport do you fly into for flights to Sitka from Chicago?
Located just 1.2 mi from the city center, Sitka is the airport most travelers will use when flying to Sitka from Chicago. Booking flights from Chicago to Sitka (SIT) should be relatively easy as there are 0 daily inbound flights from Chicago from 0 different airlines.
Can I find deals for flights from Chicago to Sitka that include hotel bookings?
Yes. In addition to deals on Chicago to Sitka flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Chicago to Sitka?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Sitka.
Can I find deals for business class flights from Chicago to Sitka?
Yes. Cheapflights offers flight deals from Chicago to Sitka by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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$695+ Cheap flights from Chicago (CHI) to Sitka (SIT)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/11. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to Sitka with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Chicago to Sitka

Round-trip from

Find flight deals from Chicago to Sitka

Cheapest flights from Chicago to SitkaExplore the most affordable flight options available from Chicago to Sitka. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 14, 2025.

Explore the most affordable flight options available from Chicago to Sitka. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 14, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to Sitka that are best for you.

Best time to book a flight from Chicago to Sitka

Have a flexible travel schedule? Discover the best time to fly to Sitka from Chicago with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Sitka

Reviews of airlines servicing Sitka

Get insights into the airlines that provide service to Sitka. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Sitka. Reviews last updated agosto 14, 2025.

Peruse reviews from past customers who have flown with Alaska Airlines from Chicago to Sitka to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Sitka. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What airport do you fly into for flights to Sitka from Chicago?

Can I find deals for flights from Chicago to Sitka that include hotel bookings?

How can I find direct flights from Chicago to Sitka?

Can I find deals for business class flights from Chicago to Sitka?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Sitka

See prices for flight routes from nearby airports that may be better suited for you.

100% Free

Book with Flexibility

Travel Smart

Cheapest flights from Chicago to Sitka
Explore the most affordable flight options available from Chicago to Sitka. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 14, 2025.