Cheap flights from Ontario to Chicago

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How to find the cheapest flight from
Ontario to Chicago (CHI)

How far in advance should I book a flight from Ontario to Chicago?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 34 days in advance, which can save you up to 86% on flights from Ontario to Chicago compared to booking the week you need them. Waiting 34 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at C$ 460. For sooner than that we have options available in the next 3 days from C$ 623.

What is the cheapest month to fly from Ontario to Chicago?

April can be a great time to fly to Chicago from Ontario with a flight ticket averaging about C$ 335. Cheapflights users have found deals in the month of April for as cheap as C$ 253. The most expensive prices can be found in the month of January.

Cheap flights from Ontario to Chicago in October, November 2020

The best prices found for Ontario to CHI flights for October, November
30 Oct - 6 Nov
C$ 285pp
YYZ
Toronto Pearson Intl
Qantas Airways
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Qantas Airways
Direct
YYZ
Toronto Pearson Intl
20 Nov - 22 Nov
C$ 292pp
YXU
London
Air Canada
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
   
2 STOPS
YXU
London
20 Nov - 22 Nov
C$ 293pp
YXU
London
Air Canada
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
   
2 STOPS
YXU
London

Ontario to Chicago 2020 flight deals

Cheap flights to Chicago from Ontario found for this year
4 Dec - 8 Dec
C$ 256pp
YXU
London
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
 
1 STOP
YXU
London
5 Dec - 8 Dec
C$ 257pp
YYZ
Toronto Pearson Intl
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YYZ
Toronto Pearson Intl
5 Dec - 8 Dec
C$ 260pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YYZ
Toronto Pearson Intl

Direct flights to Chicago from Ontario

Save time with Ontario to Chicago direct flight deals
5 Dec - 8 Dec
C$ 264pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
27 Dec - 30 Dec
C$ 281pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
17 Mar - 22 Mar
C$ 284pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

Last minute flights from Ontario to Chicago

Late deals on round-trip flights to Chicago from Ontario, departing today and this week
8 Nov - 9 Nov
C$ 334pp
YYZ
Toronto Pearson Intl
American Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
YYZ
Toronto Pearson Intl
6 Nov - 14 Nov
C$ 335pp
YYZ
Toronto Pearson Intl
American Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
YYZ
Toronto Pearson Intl
8 Nov - 10 Nov
C$ 337pp
YYZ
Toronto Pearson Intl
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YYZ
Toronto Pearson Intl

One-way flights to Chicago from Ontario

The cheapest one-way flights from Ontario to Chicago
1:30 a.m. - 11:18 a.m.
Delta
2 stops
10h 48m
YYZ - MDW
Delta
C$ 221
Delta
6:40 a.m. - 11:45 a.m.
Porter Airlines
1 stop
6h 05m
YOW - MDW
Porter Airlines
C$ 222
FareScan
1:00 a.m. - 10:41 a.m.
Air Canada
1 stop
10h 41m
YOW - ORD
Air Canada
C$ 230
KAYAK

Related info for your journey

Useful info, stats and facts about Ontario to Chicago flights.

Flight FAQs

From Ontario to Chicago

Can I find flights from Ontario to Chicago for under C$ 265 on Cheapflights?

Yes, there are multiple flights from Ontario to Chicago for under C$ 265. The cheapest flight booked recently is on United Airlines for just C$ 256, but on average you can expect to pay C$ 282.

What safety measures are being taken by airlines flying from Ontario to Chicago to control the spread of COVID-19?

Delta is one of the many airlines that have implemented additional safety measures to control the spread of COVID-19. New policies for travellers booking flights from Ontario to Chicago include masks being provided and required on board, daily cleaning and sanitization, use of HEPA filters, pre-flight testing for antibodies and symptoms, and socially-distanced seating (for a limited time). Keep in mind that policies will vary by airline.

Which airlines flying from Ontario to Chicago have flexible cancellations due to COVID-19?

Some of our airline partners flying from Ontario to Chicago have new flexible policies in place due to COVID-19. Air Canada, American Airlines, and United Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like Air Canada with this kind of flexibility.

Are there direct flights from Ontario to Chicago for under C$ 265 on Cheapflights?

Cheapflights has 20 direct flights from Ontario to Chicago under C$ 265. A good price for a direct flight from Ontario to Chicago is less than C$ 323.

Are there last-minute flights available from Ontario to Chicago for under C$ 398?

There are currently 20+ open flights from Ontario to Chicago within the next 7 days for less than C$ 398.

What days are direct flights available from Ontario to Chicago?

Direct flights are available for this route on the following days: Sunday, Thursday, Saturday.

What are the most popular airlines that fly from Ontario to Chicago?

When booking a flight from Ontario to Chicago, you may want to consider flying on Major Airline, American Airlines or Air Canada as they are the most popular for this route.

What are the most popular routes from Ontario to Chicago?

Most travellers choose Toronto Pearson Intl - Chicago O'Hare Intl, Ottawa - Chicago O'Hare Intl or London - Chicago O'Hare Intl when deciding on the best route from Ontario to Chicago.

What are the cheapest flights from Ontario to Chicago?

Looking for the cheapest flight from Ontario to Chicago? While on average our users pay C$ 386, our data indicates the cheapest price to be C$ 204. The most popular route (Toronto Pearson Intl - Chicago O'Hare Intl), is priced around C$ 300.

What are the most reliable airlines from Ontario to Chicago?

No one likes to see their flight delayed. When booking a flight from Ontario to Chicago consider choosing SkyWest Airlines (100%), Japan Airlines (100%) or Royal Jordanian (100%) as they are the most reliable in getting you off to your destination on time.

How long is the flight from Ontario to Chicago?

There are many flights that can get you from Ontario to Chicago in 1h 50m. Fly via United Airlines, Porter Airlines, or American Airlines to get the fastest option. All flights are typically direct.

What are the cheapest airlines to flying from Ontario to Chicago round-trip?

Cheapflights users have booked flights from Ontario to Chicago round-trip from C$ 256. Other airlines that can offer you cheap pricing are Air Canada, from C$ 262, and Porter Airlines, from C$ 282.

What are the cheapest airlines to fly from Ontario to Chicago one-way?

For one-way options, check prices for United Airlines. According to our data, you can fly for as low as C$ 126. Users have also found prices from C$ 157 and C$ 175 on United Airlines and Air Canada, respectively.

Destination information for Chicago

Things to know before you go. Useful info for your trip from Ontario to Chicago
Today's exchange rate
C$ 1 = $0.76
Flight duration
1h 44m
Average temperature for October in Chicago
18.0 °C
Avg rainfall for October in Chicago
66.0 mm

Airports servicing

Chatham-Kent (XCM)
Fort Frances (YAG)
Sault Ste Marie (YAM)
Attawapiskat (YAT)
Fort Albany (YFA)
Kingston, Ontario (YGK)

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)
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