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.

$133 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, Sep 25 - Mon, Sep 28

8:30 am - 2:52 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

7h 22m1 stop Montreal Pierre Elliott Trudeau Intl

2:00 pm - 4:42 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 42mnonstop

$202Air Canada

Thu, Sep 17 - Sun, Sep 20

8:30 am - 2:52 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

7h 22m1 stop Montreal Pierre Elliott Trudeau Intl

7:25 am - 10:07 amORD Chicago O'Hare Intl-YTZ Toronto Island

1h 42mnonstop

$202Air Canada

Sun, Sep 13 - Fri, Sep 25

7:00 am - 8:00 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 00mnonstop

9:20 pm - 11:59 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 39mnonstop

$212United Airlines

Sun, Sep 13 - Sun, Sep 20

7:00 am - 8:00 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 00mnonstop

12:59 pm - 3:46 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 47mnonstop

$212United Airlines

Thu, Sep 24 - Sun, Sep 27

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

2h 06mnonstop

9:55 am - 12:40 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 45mnonstop

$212Multiple Airlines

Sun, Sep 27 - Tue, Sep 29

7:00 am - 8:00 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 00mnonstop

9:55 am - 12:40 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 45mnonstop

$214Multiple Airlines

Tue, Sep 29 - Tue, Sep 29

11:53 am - 4:00 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

5h 07m1 stop Charlotte Douglas

8:30 pm - 11:26 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 56mnonstop

$222American Airlines

Wed, Oct 7 - Wed, Oct 14

1:15 pm - 2:20 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 05mnonstop

4:29 pm - 11:02 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

5h 33m1 stop New York LaGuardia

$238American Airlines

Fri, Nov 27 - Mon, Nov 30

4:35 pm - 5:30 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

1h 55mnonstop

6:10 pm - 8:50 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 40mnonstop

$257Porter Airlines

Fri, Dec 11 - Sun, Dec 13

4:35 pm - 5:30 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

1h 55mnonstop

6:10 pm - 8:50 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 40mnonstop

$265Porter Airlines

Recent last minute flight deals from Ontario to Chicago

Sat, Aug 29 - Sat, Sep 12

7:35 pm - 8:41 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 06mnonstop

2:00 pm - 4:42 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 42mnonstop

$300Air Canada

Sat, Aug 29 - Fri, Sep 11

7:35 pm - 8:41 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 06mnonstop

2:00 pm - 4:42 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 42mnonstop

$301Air Canada

Fri, Aug 28 - Fri, Sep 11

1:00 pm - 2:05 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 05mnonstop

5:53 pm - 8:44 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 51mnonstop

$310United Airlines

Fri, Aug 28 - Mon, Sep 14

7:00 am - 8:00 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 00mnonstop

9:18 pm - 11:59 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 41mnonstop

$310United Airlines

Sun, Aug 30 - Sun, Sep 13

9:44 am - 2:27 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

5h 43m1 stop Washington, D.C. Dulles Intl

8:40 pm - 11:26 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 46mnonstop

$327Multiple Airlines

Fri, Aug 28 - Fri, Sep 11

4:10 pm - 8:30 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

5h 20m1 stop Detroit Metropolitan Wayne County

8:55 am - 5:20 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

7h 25m1 stop Detroit Metropolitan Wayne County

$331Delta

Sat, Aug 29 - Sat, Sep 12

3:19 pm - 9:18 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

6h 59m1 stop New York LaGuardia

3:00 pm - 9:43 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

5h 43m1 stop Philadelphia

$337American Airlines

Wed, Aug 26 - Tue, Sep 8

5:25 pm - 10:11 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

5h 46m1 stop Washington, D.C. Reagan-National

4:53 pm - 10:35 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

4h 42m1 stop Charlotte Douglas

$428American Airlines

Sun, Aug 30 - Sun, Sep 6

11:39 am - 12:44 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 05mnonstop

2:55 pm - 5:44 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 49mnonstop

$509Porter Airlines

Sat, Aug 29 - Sun, Sep 6

11:39 am - 12:44 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 05mnonstop

2:55 pm - 5:44 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 49mnonstop

$517Porter Airlines

Recent direct flight deals from Ontario to Chicago

Fri, Sep 25 - Sun, Sep 27

7:35 pm - 8:41 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 06mnonstop

7:25 am - 10:07 amORD Chicago O'Hare Intl-YTZ Toronto Island

1h 42mnonstop

$203Air Canada

Thu, Sep 24 - Sun, Sep 27

7:35 pm - 8:41 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 06mnonstop

7:25 am - 10:07 amORD Chicago O'Hare Intl-YTZ Toronto Island

1h 42mnonstop

$203Air Canada

Thu, Sep 10 - Sun, Sep 13

5:15 pm - 6:18 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 03mnonstop

8:50 am - 11:49 amORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 59mnonstop

$212United Airlines

Mon, Sep 14 - Mon, Sep 21

9:00 pm - 10:05 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 05mnonstop

9:18 pm - 11:59 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 41mnonstop

$212United Airlines

Thu, Sep 24 - Sun, Sep 27

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

2h 06mnonstop

9:55 am - 12:40 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 45mnonstop

$212Multiple Airlines

Sun, Sep 27 - Tue, Sep 29

7:00 am - 8:00 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 00mnonstop

9:55 am - 12:40 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 45mnonstop

$214Multiple Airlines

Thu, Oct 8 - Thu, Oct 15

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

2h 10mnonstop

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

1h 59mnonstop

$256American Airlines

Fri, Nov 27 - Mon, Nov 30

4:35 pm - 5:30 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

1h 55mnonstop

6:10 pm - 8:50 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 40mnonstop

$257Porter Airlines

Fri, Dec 11 - Sun, Dec 13

4:35 pm - 5:30 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

1h 55mnonstop

6:10 pm - 8:50 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 40mnonstop

$265Porter Airlines

Tue, Nov 17 - Tue, Nov 24

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

2h 20mnonstop

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

1h 50mnonstop

$299American Airlines

Useful Info

Low season	December
High season	September
Cheapest flight	$133

Best time to beat the crowds with an average 10% drop in price.

Most popular time to fly and prices are also 31% lower on average.

Flight from Toronto to Chicago O'Hare Airport

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

Saint Joseph

Hammond

Elk Grove Village

Des Plaines

Hoffman Estates

South Holland

Portage

Oakbrook Terrace

Willowbrook

Lansing

Delavan

Alsip

Northbrook

Lisle

Valparaiso

Everything you need to know for your flight to Chicago

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Chicago (ORD)

$133 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

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

FAQs for booking Ontario to Chicago flights

Traveling to a place near Chicago?

Everything you need to know for your flight to Chicago

Information on your arrival and departure airports

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

Find direct flights for Chicago

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Flights from domestic origins to Ontario

Choose which airport to fly into in Chicago