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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

C$ 116 CHEAP FLIGHTS from Ontario to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

...and more

Travellers love KAYAK

41,299,237 searches in the past 7 days on KAYAK

Save 27% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals

Cheap Flight Deals 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.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Ontario to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Ontario to Chicago.

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

7:55 a.m. - 8:45 a.m.YTZ-MDW

1h 50mdirect

5:20 p.m. - 8:02 p.m.MDW-YTZ

1h 42mdirect

C$ 118Porter Airlines

Find Deal

Tue, 20 May - Tue, 3 Jun

2:45 p.m. - 3:51 p.m.YYZ-ORD

2h 06mdirect

7:04 a.m. - 9:58 a.m.ORD-YYZ

1h 54mdirect

C$ 128Air Canada

Find Deal

Tue, 20 May - Tue, 3 Jun

11:00 a.m. - 12:01 p.m.YYZ-ORD

2h 01mdirect

1:01 p.m. - 3:46 p.m.ORD-YYZ

1h 45mdirect

C$ 132Air Canada

Find Deal

Fri, 30 May - Sat, 31 May

5:00 p.m. - 10:41 p.m.YYZ-ORD

6h 41m1 stop

3:33 p.m. - 11:14 p.m.ORD-YYZ

6h 41m1 stop

C$ 180WestJet

Find Deal

Tue, 20 May - Tue, 3 Jun

6:30 a.m. - 1:15 p.m.YYZ-MDW

7h 45m1 stop

12:48 p.m. - 10:23 a.m.MDW-YYZ

20h 35m1 stop

C$ 180WestJet

Find Deal

Tue, 20 May - Tue, 3 Jun

4:05 p.m. - 4:54 p.m.YTZ-MDW

1h 49mdirect

5:50 p.m. - 8:32 p.m.MDW-YTZ

1h 42mdirect

C$ 180Porter Airlines

Find Deal

Fri, 23 May - Mon, 26 May

3:35 p.m. - 4:24 p.m.YTZ-MDW

1h 49mdirect

5:20 p.m. - 8:02 p.m.MDW-YTZ

1h 42mdirect

C$ 310Air Transat

Find Deal

Thu, 10 Jul - Sun, 13 Jul

6:15 a.m. - 7:59 a.m.YUL-ORD

2h 44mdirect

7:19 a.m. - 10:40 a.m.ORD-YUL

2h 21mdirect

C$ 349United Airlines

Find Deal

Fri, 23 May - Mon, 26 May

1:00 p.m. - 2:01 p.m.YYZ-ORD

2h 01mdirect

5:55 p.m. - 8:44 p.m.ORD-YYZ

1h 49mdirect

C$ 359United Airlines

Find Deal

Thu, 22 May - Wed, 28 May

7:55 a.m. - 8:45 a.m.YTZ-MDW

1h 50mdirect

5:50 p.m. - 8:32 p.m.MDW-YTZ

1h 42mdirect

C$ 504Air Transat

Find Deal

Thu, 15 May - Mon, 19 May

Useful Info

Low season	January
High season	August
Cheapest flight	C$ 116

Best time to beat the crowds but there is an average 5% increase in price.

Most popular time to fly (2% more expensive on average)

Flight from Toronto Island to Chicago Midway Airport

BrianFlew with Air CanadaYYZ-ORDOct 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.

Jo AnnFlew with Air CanadaYYZ-ORDJun 2024

It seemed that anyone who checked a bag was able to retrieve it quickly.

Verified travelerFlew with United AirlinesYYZ-ORDMar 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

Verified travelerFlew with Air CanadaYYZ-ORDFeb 2024

I would definitely choose Air Canada over dirty old United airplanes any day.

Verified travelerFlew with United AirlinesYYZ-ORDDec 2023

The departure time was very convenient with the United.

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.

Benton Harbor

New Buffalo

Portage

Merrillville

Schererville

Saint Joseph

Valparaiso

Hammond

Munster

Chesterton

Lansing

Monticello

Porter

Everything you need to know for your flight to Chicago

Cabin class

Complete your trip

Direct Flights

Flights to other cities

Origins

Other airports

Return flight deals

Cabin class types available on flights to Ontario

First Class flights to Chicagofrom C$ 805

Business Class flights to Chicagofrom C$ 770

Prem Econ Class flights to Chicagofrom C$ 496

Economy Class flights to Chicagofrom C$ 234

C$ 116 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 1/9. 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.

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

Cheap Flight Deals 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 flights from Ontario to Chicago

How does KAYAK find such low prices 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?

What is the Hacker Fare option on flights from Ontario to Chicago?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Ontario to Chicago?

Travelling to a place near Chicago?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Ontario

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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

Find direct flights for Chicago

Flights to other popular destinations

The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.

Flights from domestic origins to Chicago

Flights from all regions of Ontario to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Choose which airport to fly into in Chicago

Find deals for your return flight