Cheap flights from Ontario to Chicago

Travel > North America > United States > Ontario to Chicago flights

If you want to visit a vibrant, energetic city that's rich in heritage, culture, entertainment, and commerce, Chicago runs right up there with the big dogs. You could start by visiting downtown which is the center for government, finance, and commerce of Chicago and is encircled by The Loop, named for the elevated train tracks that loop around the central area. Tall skyscrapers such as the world's second-tallest building, the Sears Tower, and the Chicago Board of Trade are landmarks... (read more in our Chicago Travel Guide)

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Cheapest flights found for the next 6 months

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Kitchener 
London 
Niagara Falls 
Ontario, London 
Ottawa 
Toronto 
Windsor 

Check our newest flight offers to Chicago:

  • $202Porter Airlines flight Porter Airlines 
    FromToDepartureTime
    Toronto, ON (YTZ)Chicago, IL (MDW)03/01/201701:35 pm
    Chicago, IL (MDW)Toronto, ON (YTZ)03/07/201703:05 pm
    cheapoair.com check price
  • $258Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    Ontario, CA (ONT)Chicago, IL (MDW)03/22/201702:40 pm
    Chicago, IL (MDW)Ontario, CA (ONT)04/04/201707:45 pm
    flyfar.ca check price
  • $259Porter Airlines flight Porter Airlines 
    FromToDepartureTime
    Windsor, ON (YQG)Chicago, IL (MDW)02/25/201712:10 pm
    Chicago, IL (MDW)Windsor, ON (YQG)03/07/201710:20 am
    flighthub.com check price
  • $290Porter Airlines flight Porter Airlines 
    FromToDepartureTime
    Ottawa, ON (YOW)Chicago, IL (MDW)03/08/201707:15 am
    Chicago, IL (MDW)Ottawa, ON (YOW)03/14/201710:20 am
    flightnetwork.com check price
  • $373Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    London, ON (YXU)Chicago, IL (ORD)03/03/201709:15 am
    Chicago, IL (ORD)London, ON (YXU)03/18/201706:00 am
    travelgrove.com check price
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Jetblue AirwaysNew York City To Fort Lauderdale Jetblue Airways airfares from New York City in February
$251 Depart: 02/23/2017
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$2620 Depart: 06/17/2017
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Cathay PacificNew York City To Vancouver Cathay Pacific airfares from New York City in February
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Multiple AirlinesNew York City To Vigo Multiple Airlines airfares from New York City in March
$773 Depart: 03/28/2017
Return: 04/12/2017

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Multiple AirlinesPhoenix To Oranjestad Multiple Airlines airfares from Phoenix in March
$2013 Depart: 03/29/2017
Return: 04/12/2017

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