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.

$136 CHEAP FLIGHTS from Ontario to Chicago (ORD)

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Flight Deals

Cheap Flights from Ontario to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Ontario to Chicago

Fri, Nov 13 - Mon, Nov 16

4:35 pm - 5:40 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 05mnonstop

12:15 pm - 3:00 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 45mnonstop

$215Porter Airlines

Fri, Dec 4 - Sat, Dec 5

4:35 pm - 5:40 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 05mnonstop

12:15 pm - 3:00 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 45mnonstop

$215Porter Airlines

Fri, Dec 4 - Fri, Dec 11

6:23 pm - 7:43 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 20mnonstop

8:45 pm - 11:41 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 56mnonstop

$226American Airlines

Fri, Nov 20 - Sun, Nov 22

3:15 pm - 4:35 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 20mnonstop

8:45 pm - 11:59 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

2h 14mnonstop

$226American Airlines

Thu, Nov 12 - Sun, Nov 15

8:20 am - 9:23 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 03mnonstop

8:45 am - 11:27 amORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 42mnonstop

$230Air Canada

Thu, Nov 12 - Sun, Nov 15

12:05 pm - 1:20 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 15mnonstop

1:55 pm - 4:42 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 47mnonstop

$239Air Canada

Sat, Oct 31 - Sat, Oct 31

10:53 am - 11:57 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 04mnonstop

6:12 pm - 11:52 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

4h 40m1 stop Washington, D.C. Dulles Intl

$245United Airlines

Sat, Nov 7 - Sun, Nov 8

6:40 pm - 12:01 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

6h 21m1 stop Newark

11:05 am - 2:03 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 58mnonstop

$249Lufthansa

Sat, Nov 7 - Sun, Nov 8

6:40 pm - 12:01 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

6h 21m1 stop Newark

7:03 am - 9:47 amORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 44mnonstop

$257Lufthansa

Fri, Nov 6 - Sat, Nov 7

7:26 pm - 8:48 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 22mnonstop

7:00 am - 5:49 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

9h 49m1 stop Newark

$274United Airlines

Recent last minute flight deals from Ontario to Chicago

Sat, Oct 24 - Fri, Oct 30

12:15 pm - 1:25 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 10mnonstop

1:55 pm - 4:42 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 47mnonstop

$229Air Canada

Sat, Oct 24 - Fri, Oct 30

12:15 pm - 1:25 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 10mnonstop

1:55 pm - 4:42 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 47mnonstop

$230Air Canada

Mon, Oct 26 - Tue, Nov 10

4:35 pm - 5:40 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 05mnonstop

6:20 pm - 9:05 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 45mnonstop

$374Porter Airlines

Mon, Oct 26 - Mon, Nov 9

4:35 pm - 5:40 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 05mnonstop

6:20 pm - 9:05 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 45mnonstop

$387Porter Airlines

Wed, Oct 21 - Sat, Oct 24

7:29 am - 8:39 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 10mnonstop

11:45 am - 2:33 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 48mnonstop

$394Qantas Airways

Thu, Oct 22 - Sun, Oct 25

6:25 pm - 7:30 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 05mnonstop

8:30 pm - 11:29 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 59mnonstop

$394Iberia

Wed, Oct 21 - Mon, Nov 23

7:29 am - 8:39 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 10mnonstop

2:50 pm - 5:40 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 50mnonstop

$438American Airlines

Sat, Oct 24 - Sat, Nov 7

7:29 am - 8:39 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 10mnonstop

8:45 pm - 11:46 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

2h 01mnonstop

$441American Airlines

Wed, Oct 21 - Mon, Nov 23

5:15 pm - 6:30 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 15mnonstop

5:00 am - 11:48 amORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

5h 48m1 stop Newark

$510United Airlines

Thu, Oct 22 - Sat, Nov 21

10:15 am - 11:21 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 06mnonstop

6:17 pm - 9:15 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 58mnonstop

$512United Airlines

Recent direct flight deals from Ontario to Chicago

Fri, Nov 13 - Mon, Nov 16

4:35 pm - 5:40 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 05mnonstop

12:15 pm - 3:00 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 45mnonstop

$215Porter Airlines

Fri, Dec 4 - Sat, Dec 5

4:35 pm - 5:40 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 05mnonstop

12:15 pm - 3:00 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 45mnonstop

$215Porter Airlines

Fri, Dec 4 - Fri, Dec 11

6:23 pm - 7:43 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 20mnonstop

8:45 pm - 11:41 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 56mnonstop

$226American Airlines

Fri, Nov 20 - Sun, Nov 22

3:15 pm - 4:35 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 20mnonstop

8:45 pm - 11:59 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

2h 14mnonstop

$226American Airlines

Thu, Nov 12 - Sun, Nov 15

8:20 am - 9:23 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 03mnonstop

8:45 am - 11:27 amORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 42mnonstop

$230Air Canada

Thu, Nov 12 - Sun, Nov 15

12:05 pm - 1:20 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 15mnonstop

1:55 pm - 4:42 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 47mnonstop

$239Air Canada

Sat, Nov 14 - Mon, Nov 16

1:17 pm - 2:37 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 20mnonstop

8:45 pm - 11:46 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

2h 01mnonstop

$286Alaska Airlines

Sat, Nov 14 - Mon, Nov 16

6:21 pm - 7:41 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 20mnonstop

8:45 pm - 11:46 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

2h 01mnonstop

$286Multiple Airlines

Fri, Dec 11 - Sun, Dec 13

10:53 am - 11:57 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 04mnonstop

1:57 pm - 4:47 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 50mnonstop

$316United Airlines

Sat, Dec 5 - Mon, Dec 7

6:45 am - 7:54 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 09mnonstop

6:17 pm - 9:15 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 58mnonstop

$329United Airlines

Useful Info

Low season	February
High season	August
Cheapest flight	$136

Best time to beat the crowds but there is an average 4% increase in price.

Most popular time to fly with an average 13% increase in price.

Flight from Toronto to Chicago O'Hare Airport

NicholFlew with United Airlines-Aug 2026

If you are a US citizen, make sure you allow enough time for customs in Toronto Pearson airport. My trip was really quick and smooth, but I've seen it at other times where it has been busier and needed more time.

BrianFlew with Air Canada-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-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

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.

Gurnee

Merrillville

South Haven

Oak Brook

Tinley Park

Hammond

Saint Joseph

Des Plaines

Elk Grove Village

Hoffman Estates

Oakbrook Terrace

Portage

South Holland

Willowbrook

Lansing

Lisle

Alsip

Valparaiso

Northbrook

Delavan

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$136 Find Cheap Flights from Ontario to Chicago - Compare and Save

Cheap Flights from Ontario to Chicago

Recent round-trip flight deals from Ontario to Chicago

Recent one-way flight deals from Ontario to Chicago

Recent last minute flight deals from Ontario to Chicago

Recent direct flight deals from Ontario to Chicago

Good to know

Low season

High season

Cheapest flight

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

FAQs for booking Ontario to Chicago flights

Traveling to a place near Chicago?

More options for your flight to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Information on your arrival and departure airports

Cabin class types available on flights to Chicago

Find direct flights for Chicago

Flights from domestic origins to Ontario

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