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:

  • $191Porter Airlines flight Porter Airlines 
    FromToDepartureTime
    Ottawa, ON (YOW)Chicago, IL (MDW)04/20/202107:15 am
    Chicago, IL (MDW)Ottawa, ON (YOW)04/27/202107:00 am
    cheapoair.com check price
  • $191Porter Airlines flight Porter Airlines 
    FromToDepartureTime
    Ottawa, ON (YOW)Chicago, IL (MDW)02/17/202107:15 am
    Chicago, IL (MDW)Ottawa, ON (YOW)03/10/202103:00 pm
    cheapoair.com check price
  • $218Porter Airlines flight Porter Airlines 
    FromToDepartureTime
    Toronto, ON (YTZ)Chicago, IL (MDW)03/02/202109:00 am
    Chicago, IL (MDW)Toronto, ON (YTZ)03/16/202110:30 am
    cheapoair.com check price
  • $237Porter Airlines flight Porter Airlines 
    FromToDepartureTime
    Toronto, ON (YTZ)Chicago, IL (MDW)02/18/202106:10 pm
    Chicago, IL (MDW)Toronto, ON (YTZ)03/04/202103:25 pm
    cheapoair.com check price
  • $239Alaska Airlines flight Alaska Airlines 
    FromToDepartureTime
    Ontario, CA (ONT)Chicago, IL (ORD)02/06/202107:45 am
    Chicago, IL (ORD)Ontario, CA (ONT)02/11/202105:50 pm
    cheapoair.com check price
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Frontier AirlinesLas Vegas To Little Rock Frontier Airlines airfares from Las Vegas in May
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Multiple AirlinesOmaha To Charlotte Multiple Airlines airfares from Omaha in May
$612 Depart: 05/10/2020
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Jetblue AirwaysDallas To Buffalo Jetblue Airways airfares from Dallas in December
$334 Depart: 12/17/2020
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Multiple AirlinesHouston To Hamilton Multiple Airlines airfares from Houston in February
$7914 Depart: 02/16/2021
Return: 02/25/2021

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Alaska AirlinesLos Angeles To Harrisburg Alaska Airlines airfares from Los Angeles in April
$1499 Depart: 04/14/2021
Return: 04/28/2021

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