Cheap flights from Sitka to Chicago

Flights overview

Useful information for finding cheap flights from Sitka to Chicago and booking your next trip
Cheapest round-trip flights $530
Alaska 2 stops 11 hr Sat, May 30 — Sat, Jun 6
The cheapest round-trip flight from Sitka to Chicago is currently $530
Cheapest one-way flight $285
Alaska 2 stops 10 hr Wed, May 27
The cheapest one-way flight from Sitka to Chicago is currently $285
Last-minute weekend getaway $1,182
Alaska 3 stops 22 hr Thu, May 7 — Sun, May 10
The cheapest last-minute weekend getaway from Sitka to Chicago is currently $1,182
Cheapest business class flights $1,410
Alaska 2 stops 17 hr Sat, May 30 — Sat, Jun 6
The cheapest business class round-trip flight from Sitka to Chicago is currently $1,410
Fastest flight 7 hr 38 min The fastest flight with stops from Sitka to Chicago takes 7 hr 38 min
Nonstop flights None There are no direct flights on this route.

When is the cheapest time to fly?

The cheapest month to fly from Sitka to Chicago is typically October. The most expensive month to fly is typically July.
October
Cheapest
Typical prices: $570–1,250
July
Most expensive
Typical prices: $710–1,050

Popular airlines from Sitka to Chicago

  • Alaska
    from $530
    Typical price: $630–1,050
    134 weekly connecting flights
    SIT - ORD Every day

Popular airports near Sitka

  • Sitka Rocky Gutierrez Airport (SIT)
    Sitka United States 3 min 1 mi

Popular airports near Chicago

  • Chicago O'Hare International Airport (ORD)
    Chicago United States 26 min 16 mi
  • Chicago Midway International Airport (MDW)
    Chicago United States 25 min 9 mi
  • Milwaukee Mitchell International Airport (MKE)
    Milwaukee United States 1 hr 23 min 75 mi
  • Indianapolis International Airport (IND)
    Indianapolis United States 2 hr 58 min 165 mi

Frequently asked questions about flying from Sitka to Chicago

The cheapest flights from Sitka to Chicago are usually in October. Typical ticket prices in October range from $570 to $1,250.
The cheapest round-trip flight from Sitka to Chicago recently found on Google Flights was with Alaska from $530. The cheapest one-way flight was with Alaska from $285.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Alaska flight from Sitka to Chicago is $530, flying from May 30 to Jun 6.
The cheapest round-trip flight from Sitka to Chicago starts at $530 from Sat, May 30 to Sat, Jun 6. The cheapest one-way flight starts at $285 and departs on Wed, May 27.
7 hr 38 min is the shortest flight time from Sitka to Chicago.
Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.
It's easy to use Google Flights to find the cheapest days to fly from Sitka to Chicago.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.
What counts as the best airline for your flights from Sitka to Chicago really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Sitka to Chicago.

In terms of flights, Alaska is the most popular. Alaska offers 134 connecting flights per week. Alaska flies from Sitka Rocky Gutierrez Airport (SIT) to Chicago O'Hare International Airport (ORD) .

The number of connecting flights refers to distinct flights with at least one stop between Sitka and Chicago.
The cheapest round-trip flight from Sitka to Chicago recently found on Google Flights was with Alaska from $530. The cheapest one-way flight was with Alaska from $285.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Alaska flight from Sitka to Chicago is $530, flying from May 30 to Jun 6.
No airline flies direct from Sitka to Chicago.
  • There are 134 Alaska connecting flights from Sitka to Chicago per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
The cheapest last-minute deal between Sitka and Chicago at price $1,182 is offered by Alaska from Thu, May 7 to Sun, May 10.
No airline flies direct from Sitka to Chicago.
  • There are 134 Alaska connecting flights from Sitka to Chicago per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
There are no direct flights from Sitka to Chicago.
It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Sitka to Chicago, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.
The cheapest business class round-trip flights between Sitka and Chicago start at $1,410 from Sat, May 30 to Sat, Jun 6 with Alaska.
The cheapest economy class round-trip flights between Sitka and Chicago start at $530 from Sat, May 30 to Sat, Jun 6.
To book business class trips from Sitka to Chicago, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.
The best last-minute getaway deal for the next weekend between Sitka and Chicago starts at $1,182 from Thu, May 7 to Sun, May 10 with Alaska.
The cheapest last-minute deal between Sitka and Chicago at price $1,182 is offered by Alaska from Thu, May 7 to Sun, May 10.
To find last-minute flight deals from Sitka to Chicago, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.

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