Cheap flights from Alaska to Chicago

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Though residents complain about the cold weather that lasts almost through the whole year, at least on a winter day, they can duck into such popular clubs as Andy's, where there's hot jazz even at noon. The best time to visit is between May and October when the weather is the most predictable. Then you could head out to ivy-covered Wrigley Field to catch baseball's Cubs in action, or take a cruise boat under the bridges of the Chicago River at sunset.... (read more in our Chicago Travel Guide)

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Cheapest flights found for the next 6 months

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Anchorage 

Check our newest flight offers to Chicago:

  • $479United Airlines flight United Airlines 
    FromToDepartureTime
    Anchorage, AK (ANC)Chicago, IL (ORD)03/30/201809:10 pm
    Chicago, IL (ORD)Anchorage, AK (ANC)04/05/201804:10 pm
    flyfar.ca check price
  • $485United Airlines flight United Airlines 
    FromToDepartureTime
    Anchorage, AK (ANC)Chicago, IL (ORD)04/03/201811:35 pm
    Chicago, IL (ORD)Anchorage, AK (ANC)04/09/201804:08 pm
    flyfar.ca check price
  • $490United Airlines flight United Airlines 
    FromToDepartureTime
    Anchorage, AK (ANC)Chicago, IL (ORD)03/30/201809:10 pm
    Chicago, IL (ORD)Anchorage, AK (ANC)04/05/201804:10 pm
    flightnetwork.com check price
  • $498Alaska Airlines flight Alaska Airlines 
    FromToDepartureTime
    Anchorage, AK (ANC)Chicago, IL (ORD)04/03/201801:25 am
    Chicago, IL (ORD)Anchorage, AK (ANC)04/09/201806:00 am
    flyfar.ca check price
  • $499United Airlines flight United Airlines 
    FromToDepartureTime
    Anchorage, AK (ANC)Chicago, IL (ORD)04/03/201811:35 pm
    Chicago, IL (ORD)Anchorage, AK (ANC)04/09/201804:08 pm
    flightnetwork.com check price
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Chicago Pictures
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