Cheap flights from Ontario to Chicago

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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 34 days early can save you up to 86% on average compared to booking a flight this week. If booking 34 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$ 436 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$ 591 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 April. Prices to Chicago from Region of Ontario average C$ 318. You can even find prices in April for less than C$ 318, as users have found deals to Chicago from as low as C$ 240. The month of January 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 10%.

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 2022

The best prices found for Ontario to CHI flights for January, February
3 Feb. - 4 Feb.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

2 stops

18h 44m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 42m
C$ 243

United Airlines

View Deal

Deal found 21/1/22

25 Feb. - 27 Feb.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 259

Porter Airlines

View Deal

Deal found 21/1/22

25 Feb. - 28 Feb.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 260

Porter Airlines

View Deal

Deal found 22/1/22

Ontario to Chicago 2022 flight deals

Cheap flights to Chicago from Ontario found for this year
28 May - 31 May
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 50m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 40m
C$ 187

Flair Airlines

View Deal

Deal found 21/1/22

26 May - 31 May
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 50m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 40m
C$ 204

Flair Airlines

View Deal

Deal found 23/1/22

15 May - 17 May
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 50m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

6h 12m
C$ 223

Air Canada

View Deal

Deal found 22/1/22

Direct flights to Chicago from Ontario

Save time with Ontario to Chicago direct flight deals
26 May - 31 May
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 50m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 40m
C$ 204

Flair Airlines

View Deal

Deal found 23/1/22

11 Mar. - 21 Mar.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 259

Porter Airlines

View Deal

Deal found 23/1/22

7 Mar. - 12 Mar.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 53m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 42m
C$ 259

Air Canada

View Deal

Deal found 23/1/22

Last minute flights from Ontario to Chicago

Late deals on round-trip flights to Chicago from Ontario, departing today and this week
3 Feb. - 4 Feb.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

2 stops

18h 44m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 42m
C$ 243

United Airlines

View Deal

Deal found 21/1/22

29 Jan. - 31 Jan.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

13h 45m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

21h 55m
C$ 307

American Airlines

View Deal

Deal found 22/1/22

29 Jan. - 12 Feb.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

16h 51m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

17h 41m
C$ 309

American Airlines

View Deal

Deal found 22/1/22

One-way flights to Chicago All airports from Ontario

The cheapest one-way flights from Ontario to Chicago
9 Jun.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 50m
C$ 104

Flair Airlines

View Deal

Deal found 23/1/22

28 May
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 50m
C$ 109

Flair Airlines

View Deal

Deal found 21/1/22

26 Apr.
YTZ

Toronto Island

ORD

Chicago O'Hare Intl

1 stop

5h 13m
C$ 146

Air Canada

View Deal

Deal found 23/1/22

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, 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.

Can I find flights from Region of Ontario to Chicago for under C$ 200 on Cheapflights?

Yes, there are multiple flights from Region of Ontario to Chicago for under C$ 200. The cheapest flight booked recently is on Flair Airlines for just C$ 187, but on average you can expect to pay C$ 253.

Are there direct flights from Region of Ontario to Chicago for under C$ 300 on Cheapflights?

Cheapflights has 20 direct flights from Region of Ontario to Chicago under C$ 300. A good price for a direct flight from Region of Ontario to Chicago is less than C$ 267.

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: Wednesday.

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

Travellers can expect 1 flight 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$ 187, Flair 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 Flair Airlines, with whom users have recently found tickets for as low as C$ 104. However, be on the lookout for offers from Air Canada and Porter 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 Island - Chicago O'Hare Intl 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: Major Airline, 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 ANA (100%), Republic Airways (100%) or Envoy Air (93%) 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$ 196 for a flight from Region of Ontario to Chicago. The cheapest flight overall is C$ 141 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 204.

Can I fly to Chicago from Ontario right now?

Information is based on travel restrictions from Ontario to Chicago

Most visitors from Ontario need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Ontario must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Chicago.

Quarantine requirements
Visitors from Ontario are not required to quarantine after entering Chicago.

Can I fly back to Ontario from Chicago?

Returning to Ontario from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) test taken 72 hours before departing to Ontario.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Ontario.

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 6 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
American Airlines
CheapestC$ 164
AverageC$ 429
FlexibilityNo cancel fee
On-time71%
COVID-19 safety
Air Canada
CheapestC$ 177
AverageC$ 447
FlexibilityNo cancel fee
On-time67%
COVID-19 safety
Delta
CheapestC$ 186
AverageC$ 467
FlexibilityNo cancel fee
On-timeN/A
COVID-19 safety
Porter Airlines
CheapestC$ 215
AverageC$ 369
FlexibilityNo cancel fee
On-time52%
COVID-19 safety
United Airlines
CheapestC$ 221
AverageC$ 450
FlexibilityNo cancel fee
On-time69%
COVID-19 safety
WestJet
CheapestC$ 222
AverageC$ 450
FlexibilityNo cancel fee
On-time60%
COVID-19 safety

Hourly flight availability from Ontario to Chicago

See what time of day planes typically take off from Ontario to Chicago
16%of flight departuresEarly morningMidnight to 6 am
40%of flight departuresMorning6 am to noon
39%of flight departuresAfternoonNoon to 6 pm
5%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM