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Flights from Chicago to Skagway
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Flights from Chicago to Skagway Starting at NZD 2,115

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

  • Round-trip
      • ORD14:00
        22h 21m
        2 stops
        SGY09:21
        Fri, Feb 14|Chicago - Skagway|Alaska Airlines
        SGY09:36
        17h 17m
        2 stops
        ORD05:53
        Thu, Feb 20|Skagway - Chicago|Air Excursion
        NZD 2,115NZD 3,763
        44% OFF
        44% OFF
        NZD 3,763NZD 2,115

        Choose Alaska Airlines flights from Chicago to Skagway. The one-way connecting flight with Alaska Airlines departs from O'Hare International Airport on Fri, Feb 14-Thu, Feb 20, arriving at Skagway Airport. One-way Prices start from NZD 2,115 including taxes and charges.

      • ORD07:45
        30h 50m
        2 stops
        SGY11:35
        Mon, Feb 17|Chicago - Skagway|Alaska Airlines
        SGY14:55
        35h 58m
        2 stops
        ORD05:53
        Sun, Feb 23|Skagway - Chicago|Air Excursion
        NZD 2,194NZD 3,763
        42% OFF
        42% OFF
        NZD 3,763NZD 2,194

        Choose Alaska Airlines flights from Chicago to Skagway. The one-way connecting flight with Alaska Airlines departs from O'Hare International Airport on Mon, Feb 17-Sun, Feb 23, arriving at Skagway Airport. One-way Prices start from NZD 2,194 including taxes and charges.

      • ORD17:54
        20h 41m
        2 stops
        SGY11:35
        Fri, Mar 7|Chicago - Skagway|Alaska Airlines
        SGY15:25
        29h 34m
        2 stops
        ORD23:59
        Fri, Mar 14|Skagway - Chicago|Air Excursion
        NZD 2,206NZD 3,763
        41% OFF
        41% OFF
        NZD 3,763NZD 2,206

        Choose Alaska Airlines flights from Chicago to Skagway. The one-way connecting flight with Alaska Airlines departs from O'Hare International Airport on Fri, Mar 7-Fri, Mar 14, arriving at Skagway Airport. One-way Prices start from NZD 2,206 including taxes and charges.

      • ORD17:56
        20h 39m
        2 stops
        SGY11:35
        Sat, Mar 1|Chicago - Skagway|Alaska Airlines
        SGY14:55
        30h 4m
        2 stops
        ORD23:59
        Sat, Mar 8|Skagway - Chicago|Air Excursion
        NZD 2,301
        NZD 2,301

        Choose Alaska Airlines flights from Chicago to Skagway. The one-way connecting flight with Alaska Airlines departs from O'Hare International Airport on Sat, Mar 1-Sat, Mar 8, arriving at Skagway Airport. One-way Prices start from NZD 2,301 including taxes and charges.

      • ORD19:59
        18h 36m
        2 stops
        SGY11:35
        Fri, Feb 14|Chicago - Skagway|United Airlines
        SGY11:50
        15h 3m
        2 stops
        ORD05:53
        Thu, Feb 20|Skagway - Chicago|Air Excursion
        NZD 2,690
        NZD 2,690

        Choose United Airlines flights from Chicago to Skagway. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Fri, Feb 14-Thu, Feb 20, arriving at Skagway Airport. One-way Prices start from NZD 2,690 including taxes and charges.

      • ORD19:55
        18h 40m
        2 stops
        SGY11:35
        Fri, Mar 7|Chicago - Skagway|United Airlines
        SGY15:25
        11h 28m
        2 stops
        ORD05:53
        Fri, Mar 14|Skagway - Chicago|Air Excursion
        NZD 2,966
        NZD 2,966

        Choose United Airlines flights from Chicago to Skagway. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Fri, Mar 7-Fri, Mar 14, arriving at Skagway Airport. One-way Prices start from NZD 2,966 including taxes and charges.

      • ORD19:59
        18h 36m
        2 stops
        SGY11:35
        Mon, Feb 17|Chicago - Skagway|United Airlines
        SGY14:55
        11h 58m
        2 stops
        ORD05:53
        Sun, Feb 23|Skagway - Chicago|Air Excursion
        NZD 2,975
        NZD 2,975

        Choose United Airlines flights from Chicago to Skagway. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Mon, Feb 17-Sun, Feb 23, arriving at Skagway Airport. One-way Prices start from NZD 2,975 including taxes and charges.

      • ORD09:00
        27h 21m
        2 stops
        SGY09:21
        Sat, Mar 1|Chicago - Skagway|United Airlines
        SGY14:55
        21h 14m
        2 stops
        ORD15:09
        Sat, Mar 8|Skagway - Chicago|Air Excursion
        NZD 3,123
        NZD 3,123

        Choose United Airlines flights from Chicago to Skagway. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Sat, Mar 1-Sat, Mar 8, arriving at Skagway Airport. One-way Prices start from NZD 3,123 including taxes and charges.

      • CHI01:00 pm
        3h 5m
        Nonstop
        SGY02:00 pm
        Thu, Feb 20|Chicago - Skagway|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.

Chicago to Skagway flight time & flight schedules

Flight info.
Departure
Arrival
Weekly Schedule

  1. AS333

    Alaska Airlines

    07:45

    ORD

    4.7h

    10:28

    SEA

    SMTWTFS
    Search

  2. AS061

    Alaska Airlines

    07:15

    SEA

    2.6h

    08:52

    JNU

    SMTWTFS

  3. X41405

    Air Excursion

    10:30

    JNU

    1.1h

    11:35

    SGY

    SMTWTFS

  4. UA1705

    United Airlines

    09:00

    ORD

    4.7h

    11:44

    SEA

    SMTWTFS
    Search

  5. AS071

    Alaska Airlines

    20:25

    SEA

    2.5h

    21:52

    JNU

    SMTWTFS

  6. X41501

    Air Excursion

    06:00

    JNU

    1.2h

    07:10

    SGY

    SMTWTFS

  7. AS353

    Alaska Airlines

    17:28

    ORD

    4.7h

    20:11

    SEA

    SMTWTFS
    Search

  8. AS061

    Alaska Airlines

    07:15

    SEA

    2.6h

    08:52

    JNU

    SMTWTFS

  9. X41405

    Air Excursion

    10:30

    JNU

    1.1h

    11:35

    SGY

    SMTWTFS

  10. AS335

    Alaska Airlines

    17:58

    ORD

    4.6h

    20:35

    SEA

    SMTWTFS
    Search

  11. AS071

    Alaska Airlines

    20:25

    SEA

    2.5h

    21:52

    JNU

    SMTWTFS

  12. X41501

    Air Excursion

    06:00

    JNU

    1.2h

    07:10

    SGY

    SMTWTFS

  13. UA2211

    United Airlines

    19:59

    ORD

    4.7h

    22:42

    SEA

    SMTWTFS
    Search

  14. AS061

    Alaska Airlines

    07:15

    SEA

    2.6h

    08:52

    JNU

    SMTWTFS

  15. X41405

    Air Excursion

    10:30

    JNU

    1.1h

    11:35

    SGY

    SMTWTFS
Find more flights and airlines

Find the best time to fly from Chicago to Skagway

We monitor flight fares to help you find the best deals effortlessly

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

FAQ

  • When are flight tickets from Chicago (CHI) to Skagway (SGY) the cheapest?

    Airlines adjust prices for flights from Chicago to Skagway 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 Skagway (SGY) cost?

    According to Trip.com's data, the lowest price is around NZD 2,234.

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

    • The distance from Skagway Airport to downtown is about 1 km. It takes about 20 minutes by taxi.

How to find a cheap flight from Chicago to Skagway

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 Skagway. 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 Skagway

Off-season for travelApril
Peak season for travelApril
Flight distance3,773.56 km
Popular airlineAlaska Airlines

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