$95 Find Cheap Flights from Ontario to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 9/7. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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Cheap Flights from Ontario to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Ontario to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Ontario to Chicago

Wed, Aug 13 - Wed, Aug 20
Air Canada Logo
8:15 am - 9:09 amYYZ-ORD
1h 54mnonstop
Air Canada Logo
8:25 pm - 11:10 pmORD-YYZ
1h 45mnonstop
$143Air Canada
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Fri, Sep 19 - Mon, Sep 22
Air Canada Logo
8:20 am - 9:51 amYUL-ORD
2h 31mnonstop
Air Canada Logo
3:35 pm - 6:50 pmORD-YUL
2h 15mnonstop
$143Air Canada
Find Deal
Mon, Sep 1 - Fri, Sep 5
American Airlines Logo
6:30 am - 7:26 amYYZ-ORD
1h 56mnonstop
American Airlines Logo
3:05 pm - 5:47 pmORD-YYZ
1h 42mnonstop
$161American Airlines
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Sat, Aug 30 - Fri, Sep 5
American Airlines Logo
3:14 pm - 4:10 pmYYZ-ORD
1h 56mnonstop
American Airlines Logo
3:05 pm - 5:47 pmORD-YYZ
1h 42mnonstop
$163American Airlines
Find Deal
Thu, Jul 17 - Sat, Jul 19
United Airlines Logo
7:00 am - 7:59 amYYZ-ORD
1h 59mnonstop
United Airlines Logo
7:40 pm - 8:33 amORD-YYZ
11h 53m1 stop
$174United Airlines
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Thu, Oct 30 - Sun, Nov 2
United Airlines Logo
11:00 am - 11:59 amYYZ-ORD
1h 59mnonstop
United Airlines Logo
9:20 pm - 11:59 pmORD-YYZ
1h 39mnonstop
$182United Airlines
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Mon, Jul 21 - Wed, Jul 23
Logo
8:15 pm - 7:55 amYYZ-ORD
12h 40m1 stop
Logo
8:25 pm - 11:10 pmORD-YYZ
1h 45mnonstop
$198
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Fri, Jul 18 - Fri, Jul 25
Logo
8:50 am - 11:56 amYTZ-ORD
4h 06m1 stop
Logo
7:03 pm - 9:31 pmORD-YTZ
25h 28m2 stops
$335
Find Deal
Fri, Sep 5 - Sun, Sep 7
WestJet Logo
5:15 pm - 4:43 pmYOW-ORD
24h 28m2 stops
WestJet Logo
5:30 pm - 12:40 amORD-YOW
30h 10m1 stop
$374WestJet
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Fri, Aug 22 - Sun, Aug 24
WestJet Logo
5:55 am - 4:44 pmYOW-ORD
11h 49m2 stops
WestJet Logo
5:30 pm - 6:45 amORD-YOW
12h 15m1 stop
$398WestJet
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Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$95
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Montreal to Chicago O'Hare Airport

Flights from Ontario to Chicago: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from Ontario to Chicago 
Learn how KAYAK collects reviews and tips from users.
BrianFlew with Air CanadaYYZ-ORDOct 2024
Be prepared for a labyrinthine experience traversing the various levels and passages of the Toronto airport. Bring quality walking shoes, as it is likely well over a km in total walking time.
Verified travelerFlew with United AirlinesYYZ-ORDMar 2024
Carry-on baggage sizing for United US bound flights appears to be much smaller than for Canadian flights, which forced me to check my bag at the last minute. So check online ahead of time

FAQs for booking Ontario to Chicago flights

  • How does KAYAK find such low prices on flights from Ontario to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Ontario to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Ontario to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Ontario is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Ontario to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Ontario with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Ontario to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Ontario up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Everything you need to know for your flight to Chicago

Information on your arrival and departure airports

Chicago (ORD)

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