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Flights from Anchorage to Chicago
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Find Anchorage to Chicago flights starting at CAD 209.

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

  • One way
  • Round-trip
      • Cheapest direct
        ANC20:53
        6h 27m
        Nonstop
        ORD06:20
        Wed, Dec 25|Anchorage - Chicago|United Airlines
        CAD 209CAD 278
        25% OFF
        25% OFF
        CAD 278CAD 209
      • ANC21:20
        6h 1m
        Nonstop
        ORD06:21
        Sun, Nov 24|Anchorage - Chicago|United Airlines
        CAD 217CAD 278
        22% OFF
        22% OFF
        CAD 278CAD 217
      • ANC21:20
        6h 1m
        Nonstop
        ORD06:21
        Mon, Nov 25|Anchorage - Chicago|United Airlines
        CAD 218CAD 278
        21% OFF
        21% OFF
        CAD 278CAD 218
      • ANC00:33
        8h 34m
        1 stop
        ORD12:07
        Sun, Dec 8|Anchorage - Chicago|Alaska Airlines
        CAD 209
        CAD 209
      • ANC02:28
        18h 31m
        1 stop
        ORD23:59
        Mon, Jan 6|Anchorage - Chicago|Alaska Airlines
        CAD 212
        CAD 212
      • ANC14:10
        30h 48m
        1 stop
        ORD23:58
        Tue, Dec 3|Anchorage - Chicago|Delta Air Lines
        CAD 217
        CAD 217
      • ANC12:00
        8h 47m
        1 stop
        ORD23:47
        Tue, Dec 10|Anchorage - Chicago|Alaska Airlines
        CAD 220
        CAD 220
      • ANC17:45
        8h 43m
        1 stop
        ORD05:28
        Mon, Nov 18|Anchorage - Chicago|Alaska Airlines
        CAD 221
        CAD 221
      • ANC17:35
        8h 25m
        1 stop
        ORD05:00
        Sun, Nov 10|Anchorage - Chicago|Alaska Airlines
        CAD 221
        CAD 221
      • ANC01:55
        19h 4m
        1 stop
        ORD23:59
        Wed, Nov 13|Anchorage - Chicago|Alaska Airlines
        CAD 222
        CAD 222
      • ANC13:00
        3h 5m
        Nonstop
        CHI14:00
        Thu, Nov 14|Anchorage - Chicago|United Airlines
        Find More Flights
        Find More Flights

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

When is the cheapest time to fly from Anchorage to Chicago?

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.
Find Cheapest Airlines Flying from Anchorage to Chicago

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

United Airlines
From CAD 209
Alaska Airlines
From CAD 209
Delta Air Lines
From CAD 217
American Airlines
From CAD 223
ANA airlines

Find more flights and airlines

Alternative Routes for Anchorage to Chicago Flights

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

  • Cheapest
    Alaska Airlines
    ANC
    00:33
    8h 34m
    1 transfer
    ORD
    12:07
    Ted Stevens Anchorage International Airport - O'Hare International Airport
    Sun, Dec 8Alaska Airlines
    CAD 209
  • Delta Air Lines
    ANC
    17:15
    12h 43m
    2 transfer
    MDW
    08:58
    Ted Stevens Anchorage International Airport - Midway International Airport
    Sun, Dec 15Delta Air Lines
    CAD 222
  • Delta Air Lines
    ANC
    17:15
    12h 43m
    2 transfer
    MDW
    08:58
    Ted Stevens Anchorage International Airport - Midway International Airport
    Sun, Dec 15Delta Air Lines
    CAD 222
    Find More Flights

FAQ

  • When are flight tickets from Anchorage (ANC) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Anchorage to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much are flights from Anchorage (ANC) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around CAD 480.

  • 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, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.

  • What's the most popular airline for direct flights from Anchorage (ANC) to Chicago (CHI)?

    American Airlines operates 1 direct flights from Anchorage (ANC) to Chicago (CHI).

  • How many airports in Chicago (CHI)?

How to find a cheap flight from Anchorage 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 Anchorage 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 for Anchorage to Chicago Flights

Cheapest direct flight priceCAD 208
Cheapest return ticket priceCAD 446
Off-season travel monthDecember
Peak season for travelAugust
Flight distance4,590.77km
Popular airlineAlaska Airlines

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