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.

$128 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

Wed, Nov 4 - Wed, Nov 11

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

$205Porter Airlines

Sat, Oct 3 - Sun, Oct 4

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

$206Air Canada

Thu, Nov 12 - Sun, Nov 15

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

2h 05mnonstop

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

1h 46mnonstop

$206Porter Airlines

Thu, Oct 8 - Sun, Oct 11

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

2h 00mnonstop

7:09 am - 9:54 amORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 45mnonstop

$207Lufthansa

Thu, Oct 8 - Sun, Oct 11

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

2h 00mnonstop

11:05 am - 5:33 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

5h 28m1 stop Montreal Pierre Elliott Trudeau Intl

$207Air Canada

Thu, Oct 8 - Sun, Oct 11

11:00 am - 12:00 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 00mnonstop

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

1h 59mnonstop

$210Lufthansa

Tue, Nov 3 - Tue, Nov 10

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

2h 30mnonstop

9:00 am - 3:10 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

5h 10m1 stop Charlotte Douglas

$213American Airlines

Sat, Nov 14 - Tue, Nov 17

11:36 am - 1:01 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 25mnonstop

6:02 am - 11:59 amORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

4h 57m1 stop Washington, D.C. Reagan-National

$213American Airlines

Sat, Oct 3 - Sun, Oct 4

7:00 pm - 11:21 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

5h 21m1 stop Newark

7:09 am - 9:54 amORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 45mnonstop

$213United Airlines

Sat, Oct 24 - Mon, Oct 26

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

1h 58mnonstop

4:40 pm - 11:26 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

5h 46m1 stop Newark

$213United Airlines

Recent last minute flight deals from Ontario to Chicago

Tue, Sep 22 - Sun, Oct 11

8:50 am - 9:53 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 03mnonstop

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

1h 47mnonstop

$348United Airlines

Wed, Sep 23 - Sun, Oct 18

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

2h 05mnonstop

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

1h 39mnonstop

$348United Airlines

Wed, Sep 23 - Sun, Oct 18

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

2h 03mnonstop

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

1h 46mnonstop

$348Multiple Airlines

Tue, Sep 22 - Thu, Oct 15

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

2h 06mnonstop

2:15 pm - 5:01 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 46mnonstop

$348Multiple Airlines

Sat, Sep 26 - Tue, Oct 6

10:45 am - 2:52 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

5h 07m1 stop Montreal Pierre Elliott Trudeau Intl

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

1h 48mnonstop

$349Air Canada

Sat, Sep 26 - Fri, Oct 2

10:45 am - 2:52 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

5h 07m1 stop Montreal Pierre Elliott Trudeau Intl

7:25 am - 10:13 amORD Chicago O'Hare Intl-YTZ Toronto Island

1h 48mnonstop

$349Air Canada

Sat, Sep 26 - Fri, Oct 2

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

5h 07m1 stop Charlotte Douglas

4:00 pm - 11:46 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

6h 46m1 stop Philadelphia

$375American Airlines

Sat, Sep 26 - Mon, Sep 28

11:40 am - 12:45 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 05mnonstop

3:42 pm - 6:35 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 53mnonstop

$377Porter Airlines

Fri, Sep 25 - Sat, Sep 26

6:30 am - 7:40 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 10mnonstop

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

1h 56mnonstop

$377Porter Airlines

Wed, Sep 23 - Fri, Mar 5

3:13 pm - 4:18 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 05mnonstop

1:45 pm - 9:37 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

6h 52m1 stop New York LaGuardia

$420American Airlines

Recent direct flight deals from Ontario to Chicago

Wed, Nov 4 - Wed, Nov 11

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

$205Porter Airlines

Sat, Oct 3 - Sun, Oct 4

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

$206Air Canada

Thu, Nov 12 - Sun, Nov 15

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

2h 05mnonstop

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

1h 46mnonstop

$206Porter Airlines

Thu, Oct 8 - Sun, Oct 11

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

2h 00mnonstop

7:09 am - 9:54 amORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 45mnonstop

$207Lufthansa

Thu, Oct 1 - Sun, Oct 4

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

$208Air Canada

Thu, Oct 8 - Sun, Oct 11

11:00 am - 12:00 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 00mnonstop

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

1h 59mnonstop

$210Lufthansa

Wed, Nov 4 - Sun, Nov 8

3:15 pm - 4:35 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

$231American Airlines

Mon, Dec 7 - Sun, Dec 13

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

2h 30mnonstop

9:42 am - 12:32 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 50mnonstop

$231American Airlines

Sat, Oct 31 - Tue, Nov 3

5:55 pm - 7:05 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 10mnonstop

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

1h 50mnonstop

$231United Airlines

Fri, Nov 6 - Fri, Nov 6

6:45 am - 7:54 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

$231United Airlines

Useful Info

Low season	December
High season	August
Cheapest flight	$128

Best time to beat the crowds with an average 15% drop 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.

Merrillville

Gurnee

South Haven

Oak Brook

Tinley Park

Hammond

Saint Joseph

Des Plaines

Elk Grove Village

Hoffman Estates

Portage

South Holland

Oakbrook Terrace

Willowbrook

Lansing

Alsip

Delavan

Lisle

Northbrook

Valparaiso

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$128 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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