$100 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 3/16. 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
$175
Overall average: $301
Air Canada
Fri 5/1Mon 5/4
YUL - ORD • Non-stop
Cheapest one-way
$100
Typical prices: $197-$298
Air Canada
Mon 3/16
YUL - 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

Fri, May 1 - Mon, May 4
Air Canada Logo
6:30 pm - 8:08 pm
YUL
-
ORD
2h 38mnonstop
Air Canada Logo
11:05 am - 2:16 pm
ORD
-
YUL
2h 11mnonstop
$175Air Canada
Sat, Mar 14 - Mon, Mar 16
Air Canada Logo
9:25 am - 11:18 am
YUL
-
ORD
2h 53mnonstop
Air Canada Logo
7:15 am - 10:20 am
ORD
-
YUL
2h 05mnonstop
$176Air Canada
Sat, Mar 28 - Sat, Apr 4
Air Canada Logo
9:25 am - 11:18 am
YUL
-
ORD
2h 53mnonstop
Air Canada Logo
8:40 am - 11:51 am
ORD
-
YUL
2h 11mnonstop
$178Air Canada
Thu, Mar 12 - Mon, Mar 16
Air Canada Logo
6:25 pm - 8:10 pm
YUL
-
ORD
2h 45mnonstop
Air Canada Logo
12:50 pm - 3:57 pm
ORD
-
YUL
2h 07mnonstop
$179Air Canada
Wed, Mar 18 - Mon, Mar 23
Air Canada Logo
1:10 pm - 2:55 pm
YUL
-
ORD
2h 45mnonstop
Air Canada Logo
3:35 pm - 6:40 pm
ORD
-
YUL
2h 05mnonstop
$184Air Canada
Wed, Mar 25 - Wed, Apr 1
United Airlines Logo
6:00 am - 8:00 am
YUL
-
ORD
3h 00mnonstop
United Airlines Logo
6:01 pm - 12:13 am
ORD
-
YUL
5h 12m
1 stop
$185United Airlines
Mon, May 4 - Sat, May 9
United Airlines Logo
6:35 pm - 11:44 pm
YUL
-
ORD
6h 09m
1 stop
United Airlines Logo
6:03 pm - 9:26 pm
ORD
-
YUL
2h 23mnonstop
$191United Airlines
Thu, Mar 12 - Sun, Mar 15
Multiple Airlines Logo
1:10 pm - 2:55 pm
YUL
-
ORD
2h 45mnonstop
Multiple Airlines Logo
6:00 am - 3:16 pm
ORD
-
YUL
8h 16m
1 stop
$200Multiple Airlines
Wed, Mar 25 - Tue, Mar 31
American Airlines Logo
1:10 pm - 2:10 pm
YYZ
-
ORD
2h 00mnonstop
American Airlines Logo
8:12 am - 10:56 am
ORD
-
YYZ
1h 44mnonstop
$208American Airlines
Tue, Mar 10 - Tue, Mar 17
Multiple Airlines Logo
3:00 pm - 6:29 pm
YTZ
-
ORD
28h 29m
1 stop
Multiple Airlines Logo
12:05 pm - 8:03 pm
ORD
-
YTZ
30h 58m
2 stops
$272Multiple Airlines
Useful Info

Good to know

Low seasonNovember
Cheapest flight$100
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 1% 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 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
Lansing
Pleasant Prairie
Elmhurst
Lisle
Valparaiso

Everything you need to know for your flight to Chicago

Information on your arrival and departure airports

Chicago (ORD)