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Latest Flight Deals from Skagway to Chicago

Book one-way or return flights from Skagway to Chicago from as little as TWD 40,108. Choose from the popular airlines below and book your flight today!

  • Round-trip
      • SGY05:55
        14h 44m
        2 stops
        ORD23:39
        Tue, Jul 23|Skagway - Chicago|Air Excursion
        ORD06:00
        26h 40m
        2 stops
        SGY05:40
        Mon, Jul 29|Chicago - Skagway|Alaska Airlines
        TWD 40,108TWD 58,473
        31% OFF
        31% OFF
        TWD 58,473TWD 40,108
      • SGY14:55
        12h 45m
        2 stops
        ORD06:40
        Sun, Jul 21|Skagway - Chicago|Air Excursion
        ORD00:59
        13h 16m
        2 stops
        SGY11:15
        Sat, Jul 27|Chicago - Skagway|Alaska Airlines
        TWD 41,516TWD 58,473
        28% OFF
        28% OFF
        TWD 58,473TWD 41,516
      • SGY13:00
        3h 5m
        Direct
        CHI14:00
        Tue, Jul 9|Skagway - Chicago|Air Excursion
        Find More Flights
        Find More Flights

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

Searching for the best last minute flight from Skagway to Chicago? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Skagway to Chicago. Stay updated on price trends and snag the best deals for your upcoming trip.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Alternative Routes from Skagway to Chicago

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Skagway to Chicago.

  • Cheapest
    Air Excursion
    SGY
    05:55
    14h 44m
    4 transfer
    ORD
    23:39
    Skagway Airport - O'Hare International Airport
    Tue, Jul 23Air Excursion
    TWD 40,116
  • Air Excursion
    SGY
    05:55
    14h 44m
    4 transfer
    ORD
    23:39
    Skagway Airport - O'Hare International Airport
    Tue, Jul 23Air Excursion
    TWD 40,116
    Find More Flights

How do I find the cheapest flights?

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

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

    According to Trip.com's data, the lowest price is around TWD 40,341.

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

    • The distance from O'Hare International Airport to downtown is about 25km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14km. It takes about 30 minutes by taxi.

How to find a cheap flight from Skagway to Chicago

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 Skagway to Chicago. 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 Skagway to Chicago

Off-season for travel

September

Peak season for travel

July

Flight distance

3,773.56km

Popular airline

Air Excursion, LLC

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