Cheap flights from Ontario to Chicago

YYZ — CHI
31 Jan — 7 Feb1
Return
1 adult
Economy
From?
To?
Tue 31/1
Tue 7/2

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

Users have found that booking a flight from Region of Ontario to Chicago at least 60 days early can save you up to 45% on average compared to booking a flight this week. If booking 60 days before your flight isn’t an option for you, users have found flights from Region of Ontario to Chicago for as little as C$ 385 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as C$ 472 for flights departing within the next 3 days.

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

The best pricing can be found in the month of June. Prices to Chicago from Region of Ontario average C$ 348. You can even find prices in June for less than C$ 348, as users have found deals to Chicago from as low as C$ 217. The month of March appears to be one of the more expensive times to travel to Chicago from Region of Ontario. Flying in the targeted month can save you up to 14%.

When is the cheapest time to fly from Region of Ontario to Chicago (ON - CHI)?

When flying from Region of Ontario to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap flights from Ontario to Chicago in January, February 2023

The best prices found for Ontario to CHI flights for January, February
22 Feb. - 26 Feb.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 275

Porter Airlines

Deal found 24/1

16 Feb. - 19 Feb.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 279

Porter Airlines

Deal found 23/1

28 Feb. - 4 Mar.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 281

Porter Airlines

Deal found 25/1

Ontario to Chicago 2023 flight deals

Cheap flights to Chicago from Ontario found for this year
2 Mar. - 5 Mar.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 270

Porter Airlines

Deal found 23/1

1 Mar. - 5 Mar.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 273

Porter Airlines

Deal found 23/1

24 Mar. - 26 Mar.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m
C$ 274

Porter Airlines

Deal found 24/1

Cheap United Airlines flights from Ontario to Chicago

18 Feb. - 5 Mar.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 54m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

8h 53m
C$ 344

United Airlines

Deal found 25/1

27 Feb. - 4 Mar.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 00m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

5h 16m
C$ 345

United Airlines

Deal found 26/1

18 Feb. - 28 Feb.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

4h 54m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

4h 52m
C$ 346

United Airlines

Deal found 24/1

Cheap American Airlines flights from Ontario to Chicago

11 Mar. - 18 Mar.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 08m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 35m
C$ 314

American Airlines

Deal found 24/1

24 Feb. - 26 Feb.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 06m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

15h 30m
C$ 322

American Airlines

Deal found 23/1

23 Feb. - 1 Mar.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 06m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

6h 35m
C$ 325

American Airlines

Deal found 24/1

Direct flights to Chicago from Ontario

Save time with Ontario to Chicago direct flight deals
2 Mar. - 5 Mar.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 51m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 43m
C$ 195

Air Canada

Deal found 23/1

2 Mar. - 5 Mar.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 270

Porter Airlines

Deal found 23/1

3 Apr. - 14 Apr.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 47m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 42m
C$ 273

Porter Airlines

Deal found 24/1

Last minute flights from Ontario to Chicago

Late deals on round-trip flights to Chicago from Ontario, departing today and this week
1 Feb. - 8 Feb.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

11h 07m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

24h 15m
C$ 297

Multiple Airlines

Deal found 25/1

1 Feb. - 14 Feb.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

11h 07m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

2 stops

24h 34m
C$ 349

Multiple Airlines

Deal found 24/1

1 Feb. - 14 Feb.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

14h 44m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

13h 10m
C$ 352

Multiple Airlines

Deal found 24/1

One-way flights to Chicago from Ontario

The cheapest one-way flights from Ontario to Chicago
22 Feb.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
C$ 160

Porter Airlines

Deal found 25/1

3 Mar.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
C$ 162

Porter Airlines

Deal found 23/1

21 Mar.
YKF

Toronto Kitchener-Waterloo

ORD

Chicago O'Hare Intl

2 stops

17h 55m
C$ 164

Multiple Airlines

Deal found 26/1

Related info for your journey

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

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, Porter 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.

Can I find flights from Region of Ontario to Chicago for under C$ 300 on Cheapflights?

Yes, there are multiple flights from Region of Ontario to Chicago for under C$ 300. The cheapest flight booked recently is on Porter Airlines for just C$ 270, but on average you can expect to pay C$ 286.

Are there direct flights from Region of Ontario to Chicago for under C$ 200 on Cheapflights?

Cheapflights has 20 direct flights from Region of Ontario to Chicago under C$ 200. A good price for a direct flight from Region of Ontario to Chicago is less than C$ 285.

Are there last-minute flights available from Region of Ontario to Chicago for under C$ 300?

There are currently 20+ open flights from Region of Ontario to Chicago within the next 7 days for less than C$ 300.

What days are direct flights available from Region of Ontario to Chicago?

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

How many flights depart from Region of Ontario to Chicago on average per day?

Travellers can expect 5 flights from Region of Ontario to Chicago on average per day.
Morning (6am - Midday) - 100% of flight departures

How long is the flight from Region of Ontario to Chicago?

For as low as C$ 270, Porter Airlines can have you in Chicago from Region of Ontario in 1h 50m. Region of Ontario and Chicago are separated by a distance of 703 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

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

The cheapest airline one-way is Porter Airlines, with whom users have recently found tickets for as low as C$ 160. However, be on the lookout for offers from Air Canada and American Airlines, as they are both options that can get you from Region of Ontario to Chicago for a low price.

What are the most popular routes from Region of Ontario to Chicago?

When deciding which route to take from Region of Ontario to Chicago consider Toronto Pearson Intl - Chicago O'Hare Intl, Toronto Island - Chicago Midway or Toronto Pearson Intl - Chicago Midway as they are the most popular.

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

Before booking your flight from Region of Ontario to Chicago check out the most popular airlines for this route: Undisclosed Carrier, American Airlines or Air Canada.

What are the most reliable airlines from Region of Ontario to Chicago?

No one likes to see their flight delayed. When booking a flight from Region of Ontario to Chicago consider choosing Copa Airlines (86%), Envoy Air (86%) or Republic Airways (85%) as they are the most reliable in getting you off to your destination on time.

What are the cheapest flights from Region of Ontario to Chicago?

On average you can expect to pay C$ 1,646 for a flight from Region of Ontario to Chicago. The cheapest flight overall is C$ 273 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 314.

Departure points for flights from Ontario to Chicago

Select to see more specific information for flights to Chicago from all departure points in Ontario

Top 10 airlines flying from Ontario to Chicago

The chart below displays the airlines Cheapflights users travelling from Ontario to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapestC$ 26AverageC$ 41FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
WestJetCheapestC$ 128AverageC$ 422FlexibilityNo cancel feeOn-time60%COVID-19 safety
Search WestJet flights
DeltaCheapestC$ 166AverageC$ 320FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
SwoopCheapestC$ 171AverageC$ 185FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Swoop flights
Flair AirlinesCheapestC$ 177AverageC$ 238FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Flair Airlines flights
American AirlinesCheapestC$ 210AverageC$ 406FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
Porter AirlinesCheapestC$ 224AverageC$ 322FlexibilityNo cancel feeOn-time52%COVID-19 safety
Search Porter Airlines flights
Air CanadaCheapestC$ 247AverageC$ 572FlexibilityNo cancel feeOn-time67%COVID-19 safety
Search Air Canada flights
United AirlinesCheapestC$ 267AverageC$ 643FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
Air New ZealandCheapestC$ 283AverageC$ 393FlexibilityNo cancel feeOn-time78%COVID-19 safety
Search Air New Zealand flights

Hourly flight availability from Ontario to Chicago

See what time of day planes typically take off from Ontario to Chicago
24%of flight departuresEarly morningMidnight to 6 am
32%of flight departuresMorning6 am to noon
35%of flight departuresAfternoonNoon to 6 pm
9%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM
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