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.

$157 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

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

$227Air 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

$228Air Canada

Sat, Oct 31 - Sun, Nov 1

7:44 pm - 8:29 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

13h 45m1 stop Washington, D.C. Dulles Intl

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

1h 58mnonstop

$231Lufthansa

Sat, Dec 5 - Sat, Dec 5

8:35 am - 9:44 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 09mnonstop

6:15 pm - 11:52 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

4h 37m1 stop Washington, D.C. Dulles Intl

$232Lufthansa

Fri, Dec 11 - Sat, Dec 12

7:44 pm - 11:29 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

4h 45m1 stop Washington, D.C. Dulles Intl

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

1h 58mnonstop

$245United Airlines

Fri, Nov 27 - Sat, Nov 28

7:44 pm - 12:01 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

5h 17m1 stop Washington, D.C. Dulles Intl

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

1h 44mnonstop

$245United Airlines

Fri, Nov 6 - Mon, Nov 9

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

$263Porter Airlines

Fri, Nov 20 - Sun, Nov 22

10:35 am - 11:40 amYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 05mnonstop

6:20 pm - 9:06 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 46mnonstop

$263Porter Airlines

Thu, Nov 19 - Thu, Nov 19

7:09 am - 8:39 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 30mnonstop

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

2h 14mnonstop

$305American Airlines

Thu, Nov 19 - Thu, Nov 19

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

$305American Airlines

Recent last minute flight deals from Ontario to Chicago

Sun, Oct 11 - Thu, Oct 15

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

$351American Airlines

Mon, Oct 12 - Fri, Oct 16

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

2h 10mnonstop

2:00 pm - 4:48 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 48mnonstop

$369Air Canada

Sun, Oct 11 - Thu, Oct 15

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

2h 10mnonstop

2:00 pm - 4:48 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 48mnonstop

$369Air Canada

Sun, Oct 11 - Fri, Oct 16

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

2h 05mnonstop

8:06 am - 10:59 amORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 53mnonstop

$384American Airlines

Sat, Oct 10 - Sat, Oct 17

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

2h 05mnonstop

9:46 am - 12:34 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 48mnonstop

$394Porter Airlines

Tue, Oct 13 - Tue, Oct 20

2:26 pm - 8:30 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

7h 04m1 stop Detroit Metropolitan Wayne County

5:29 pm - 10:56 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

4h 27m1 stop Detroit Metropolitan Wayne County

$406Delta

Mon, Oct 12 - Sat, Oct 31

2:26 pm - 6:29 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

5h 03m1 stop Detroit Metropolitan Wayne County

7:00 am - 11:19 amORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

3h 19m1 stop Detroit Metropolitan Wayne County

$407Delta

Tue, Oct 13 - Sat, Nov 14

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

2h 06mnonstop

2:30 pm - 11:26 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

7h 56m1 stop Newark

$436United Airlines

Tue, Oct 13 - Sat, Nov 14

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

2h 00mnonstop

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

1h 58mnonstop

$436United Airlines

Tue, Oct 13 - Sat, Oct 17

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

2h 10mnonstop

9:46 am - 12:34 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 48mnonstop

$547Porter Airlines

Recent direct 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

$227Air 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

$228Air Canada

Mon, Oct 19 - Thu, Oct 22

8:50 am - 9:48 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

1h 58mnonstop

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

1h 39mnonstop

$259United Airlines

Fri, Nov 6 - Mon, Nov 9

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

$263Porter Airlines

Fri, Nov 20 - Sun, Nov 22

10:35 am - 11:40 amYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 05mnonstop

6:20 pm - 9:06 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 46mnonstop

$263Porter Airlines

Wed, Nov 25 - Fri, Nov 27

8:35 am - 9:44 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 09mnonstop

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

1h 50mnonstop

$305United Airlines

Thu, Nov 19 - Thu, Nov 19

7:09 am - 8:39 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 30mnonstop

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

2h 14mnonstop

$305American Airlines

Thu, Nov 19 - Thu, Nov 19

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

$305American Airlines

Sat, Nov 28 - Sun, Nov 29

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

2h 09mnonstop

10:15 am - 12:52 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 37mnonstop

$305Multiple Airlines

Fri, Nov 27 - Wed, Dec 2

3:35 pm - 4:44 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 09mnonstop

4:30 pm - 7:10 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 40mnonstop

$305Multiple Airlines

Useful Info

Low season	December
High season	August
Cheapest flight	$157

Best time to beat the crowds with an average 14% drop in price.

Most popular time to fly with an average 14% 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.

Merrillville

Gurnee

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

Delavan

Valparaiso

Northbrook

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$157 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

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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?

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

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Flights from domestic origins to Ontario

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