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Flights from Chicago to Sitka Starting at NZD 926

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • Round-trip
      • ORD08:00
        37h 27m
        2 stops
        SIT18:27
        Wed, Dec 25|Chicago - Sitka|Alaska Airlines
        SIT11:35
        14h 55m
        2 stops
        ORD05:30
        Tue, Dec 31|Sitka - Chicago|Alaska Airlines
        NZD 926NZD 1,672
        45% OFF
        45% OFF
        NZD 1,672NZD 926

        Choose Alaska Airlines flights from Chicago to Sitka. The one-way connecting flight with Alaska Airlines departs from O'Hare International Airport on Wed, Dec 25-Tue, Dec 31, arriving at Sitka Rocky Gutierrez Airport. One-way Prices start from NZD 926 including taxes and charges.

      • ORD07:45
        13h 33m
        1 stop
        SIT18:18
        Fri, Jan 10|Chicago - Sitka|Alaska Airlines
        SIT11:36
        9h 23m
        1 stop
        ORD23:59
        Fri, Jan 17|Sitka - Chicago|Alaska Airlines
        NZD 938NZD 1,672
        44% OFF
        44% OFF
        NZD 1,672NZD 938

        Choose Alaska Airlines flights from Chicago to Sitka. The one-way connecting flight with Alaska Airlines departs from O'Hare International Airport on Fri, Jan 10-Fri, Jan 17, arriving at Sitka Rocky Gutierrez Airport. One-way Prices start from NZD 938 including taxes and charges.

      • ORD09:20
        11h 58m
        1 stop
        SIT18:18
        Fri, Jan 10|Chicago - Sitka|United Airlines
        SIT11:36
        15h 24m
        1 stop
        ORD06:00
        Fri, Jan 17|Sitka - Chicago|Alaska Airlines
        NZD 970NZD 1,672
        42% OFF
        42% OFF
        NZD 1,672NZD 970

        Choose United Airlines flights from Chicago to Sitka. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Fri, Jan 10-Fri, Jan 17, arriving at Sitka Rocky Gutierrez Airport. One-way Prices start from NZD 970 including taxes and charges.

      • ORD20:04
        25h 14m
        1 stop
        SIT18:18
        Mon, Jan 13|Chicago - Sitka|United Airlines
        SIT11:36
        15h 24m
        1 stop
        ORD06:00
        Mon, Jan 20|Sitka - Chicago|Alaska Airlines
        NZD 1,006
        NZD 1,006

        Choose United Airlines flights from Chicago to Sitka. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Mon, Jan 13-Mon, Jan 20, arriving at Sitka Rocky Gutierrez Airport. One-way Prices start from NZD 1,006 including taxes and charges.

      • ORD06:32
        14h 50m
        1 stop
        SIT18:22
        Sun, Dec 8|Chicago - Sitka|Alaska Airlines
        SIT11:23
        15h 33m
        1 stop
        ORD05:56
        Thu, Dec 12|Sitka - Chicago|Alaska Airlines
        NZD 1,052
        NZD 1,052

        Choose Alaska Airlines flights from Chicago to Sitka. The one-way connecting flight with Alaska Airlines departs from O'Hare International Airport on Sun, Dec 8-Thu, Dec 12, arriving at Sitka Rocky Gutierrez Airport. One-way Prices start from NZD 1,052 including taxes and charges.

      • ORD07:45
        13h 33m
        1 stop
        SIT18:18
        Mon, Jan 13|Chicago - Sitka|Alaska Airlines
        SIT11:36
        9h 23m
        1 stop
        ORD23:59
        Mon, Jan 20|Sitka - Chicago|Alaska Airlines
        NZD 1,060
        NZD 1,060

        Choose Alaska Airlines flights from Chicago to Sitka. The one-way connecting flight with Alaska Airlines departs from O'Hare International Airport on Mon, Jan 13-Mon, Jan 20, arriving at Sitka Rocky Gutierrez Airport. One-way Prices start from NZD 1,060 including taxes and charges.

      • ORD13:07
        32h 15m
        1 stop
        SIT18:22
        Tue, Dec 3|Chicago - Sitka|Alaska Airlines
        SIT11:23
        14h 56m
        1 stop
        ORD05:19
        Mon, Dec 9|Sitka - Chicago|Alaska Airlines
        NZD 1,074
        NZD 1,074

        Choose Alaska Airlines flights from Chicago to Sitka. The one-way connecting flight with Alaska Airlines departs from O'Hare International Airport on Tue, Dec 3-Mon, Dec 9, arriving at Sitka Rocky Gutierrez Airport. One-way Prices start from NZD 1,074 including taxes and charges.

      • ORD17:00
        28h 22m
        1 stop
        SIT18:22
        Wed, Dec 4|Chicago - Sitka|Alaska Airlines
        SIT11:23
        9h 24m
        1 stop
        ORD23:47
        Tue, Dec 10|Sitka - Chicago|Alaska Airlines
        NZD 1,086
        NZD 1,086

        Choose Alaska Airlines flights from Chicago to Sitka. The one-way connecting flight with Alaska Airlines departs from O'Hare International Airport on Wed, Dec 4-Tue, Dec 10, arriving at Sitka Rocky Gutierrez Airport. One-way Prices start from NZD 1,086 including taxes and charges.

      • ORD06:00
        31h 43m
        2 stops
        SIT10:43
        Wed, Jan 1|Chicago - Sitka|Alaska Airlines
        SIT19:10
        43h 49m
        2 stops
        ORD17:59
        Tue, Jan 7|Sitka - Chicago|Alaska Airlines
        NZD 1,099
        NZD 1,099

        Choose Alaska Airlines flights from Chicago to Sitka. The one-way connecting flight with Alaska Airlines departs from O'Hare International Airport on Wed, Jan 1-Tue, Jan 7, arriving at Sitka Rocky Gutierrez Airport. One-way Prices start from NZD 1,099 including taxes and charges.

      • ORD06:00
        15h 27m
        1 stop
        SIT18:27
        Mon, Dec 2|Chicago - Sitka|Alaska Airlines
        SIT11:23
        15h 29m
        1 stop
        ORD05:52
        Sun, Dec 8|Sitka - Chicago|Alaska Airlines
        NZD 1,123
        NZD 1,123

        Choose Alaska Airlines flights from Chicago to Sitka. The one-way connecting flight with Alaska Airlines departs from O'Hare International Airport on Mon, Dec 2-Sun, Dec 8, arriving at Sitka Rocky Gutierrez Airport. One-way Prices start from NZD 1,123 including taxes and charges.

      • CHI13:00
        3h 5m
        Nonstop
        SIT14:00
        Mon, Dec 9|Chicago - Sitka|Alaska Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Find the best time to fly from Chicago to Sitka

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Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Alternative Routes from Chicago to Sitka

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Chicago to Sitka.

  • Cheapest
    Alaska Airlines
    ORD
    08:00
    37h 27m
    4 transfer
    SIT
    18:27
    O'Hare International Airport - Sitka Rocky Gutierrez Airport
    Wed, Dec 25Alaska Airlines
    NZD 926
  • Frontier Airlines
    MDW
    22:04
    23h 23m
    4 transfer
    SIT
    18:27
    Midway International Airport - Sitka Rocky Gutierrez Airport
    Mon, Dec 30Frontier Airlines
    NZD 1,187
  • Frontier Airlines
    MDW
    22:04
    23h 23m
    4 transfer
    SIT
    18:27
    Midway International Airport - Sitka Rocky Gutierrez Airport
    Mon, Dec 30Frontier Airlines
    NZD 1,187
    Find More Flights

FAQ

  • When are flight tickets from Chicago (CHI) to Sitka (SIT) the cheapest?

    Airlines adjust prices for flights from Chicago to Sitka based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Chicago (CHI) to Sitka (SIT) cost?

    According to Trip.com's data, the lowest price is around NZD 914.

  • What is the transportation method from the main airport to downtown in Sitka?

    • The distance from Sitka Rocky Gutierrez Airport to downtown is about 2 km. It takes about 20 minutes by taxi.

How to find a cheap flight from Chicago to Sitka

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Sitka. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Information from Chicago to Sitka

Off-season for travelSeptember
Peak season for travelSeptember
Flight distance3,740.01 km
Popular airlineAlaska Airlines

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