$106 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 2/3. 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, 0 bags

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Everything you should know

Cheapest round-trip
$184
Overall average: $285
American Airlines
Tue 2/17Tue 2/24
YYZ - ORD • Non-stop
Cheapest non-stop
$193
Typical prices: $257-$335
Air Canada
Tue 2/3Fri 2/6
YYZ - ORD • Non-stop
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Flight Deals
Useful Info
Flight Deals

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

Tue, Feb 17 - Tue, Feb 24
American Airlines Logo
11:40 am - 12:35 pm
YYZ
-
ORD
1h 55mnonstop
American Airlines Logo
6:00 am - 1:00 pm
ORD
-
YYZ
6h 00m1 stop
$184American Airlines
Thu, Feb 5 - Sun, Feb 8
American Airlines Logo
6:00 am - 7:15 am
YYZ
-
ORD
2h 15mnonstop
American Airlines Logo
8:09 am - 3:30 pm
ORD
-
YYZ
6h 21m1 stop
$185American Airlines
Tue, Feb 3 - Fri, Feb 6
Air Canada Logo
6:45 pm - 7:45 pm
YYZ
-
ORD
2h 00mnonstop
Air Canada Logo
8:40 pm - 11:19 pm
ORD
-
YYZ
1h 39mnonstop
$193Air Canada
Wed, Jan 28 - Sun, Feb 1
Air Canada Logo
4:50 pm - 5:48 pm
YYZ
-
ORD
1h 58mnonstop
Air Canada Logo
8:40 pm - 11:19 pm
ORD
-
YYZ
1h 39mnonstop
$194Air Canada
Fri, Jan 30 - Sun, Feb 1
United Airlines Logo
9:00 pm - 10:05 pm
YYZ
-
ORD
2h 05mnonstop
United Airlines Logo
9:15 pm - 11:59 pm
ORD
-
YYZ
1h 44mnonstop
$199United Airlines
Thu, Feb 19 - Mon, Feb 23
Delta Logo
6:00 am - 1:20 pm
YUL
-
ORD
8h 20m1 stop
Delta Logo
10:35 am - 3:55 pm
ORD
-
YUL
4h 20m1 stop
$217Delta
Thu, Feb 19 - Mon, Feb 23
Delta Logo
6:00 am - 1:20 pm
YUL
-
ORD
8h 20m1 stop
Delta Logo
10:35 am - 3:55 pm
ORD
-
YUL
4h 20m1 stop
$218Delta
Thu, Feb 5 - Sun, Feb 8
Multiple Airlines Logo
7:00 am - 10:36 pm
YOW
-
ORD
16h 36m1 stop
Multiple Airlines Logo
4:38 pm - 5:15 pm
ORD
-
YOW
23h 37m1 stop
$260Multiple Airlines
Thu, Feb 5 - Sun, Feb 8
Multiple Airlines Logo
7:00 am - 10:36 pm
YOW
-
ORD
16h 36m1 stop
Multiple Airlines Logo
4:38 pm - 5:15 pm
ORD
-
YOW
23h 37m1 stop
$267Multiple Airlines
Mon, Feb 23 - Thu, Feb 26
United Airlines Logo
5:40 pm - 11:43 pm
YXU
-
ORD
7h 03m2 stops
United Airlines Logo
7:10 am - 5:05 pm
ORD
-
YXU
8h 55m2 stops
$574United Airlines
Useful Info

Good to know

Low seasonNovember
Cheapest flight$107
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 1% increase in price.
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 Canada
YYZ
-
ORD
Oct 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 Airlines
YYZ
-
ORD
Mar 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Gurnee
South Haven
Merrillville
Oak Brook
Saint Joseph
Tinley Park
Elk Grove Village
Des Plaines
Hoffman Estates
Hammond
Willowbrook
Portage
South Holland
Delavan
Northbrook
Pleasant Prairie
Lansing
Elmhurst
Valparaiso
Lisle

Everything you need to know for your flight to Chicago

Information on your arrival and departure airports

Chicago (ORD)