Cheap flights from Toronto to Chicago

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The best prices from Toronto to Chicago are usually found in February or March, booked 60 days in advance, depart on a Wednesday or Thursday and return on a Monday

How to find the cheapest flight from
Toronto (YTO) to Chicago (CHI)

YTO - CHI
Price
C$ 288 - C$ 359
CHI
Temperature
1 - 29 °C
CHI
Rainfall
17 - 109 mm

Popular in

August

High demand for flights, 9% potential price rise

Cheapest in

February

Best time to find cheap flights, 12% potential price drop

Round-trip from

C$ 288

From Toronto to Chicago

One-way from

C$ 162

One-way flight from Toronto to Chicago

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Toronto to Chicago?

Travellers have found that booking a Tuesday departure is the best way to save up to 8% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

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

Find a great deal and save up to 81% by booking at least 57 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Toronto to Chicago within the next two weeks, with the cheapest ticket starting at C$ 437.

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

Flights from Toronto to Chicago lean towards being more expensive in August. Prices are generally better when you fly from Toronto to Chicago in February, with the cheapest ticket starting at C$ 241.

When is the cheapest time to fly from Toronto to Chicago (YTO - CHI)?

Unlike in the evening, when flights are generally more expensive, you can save up to 11% on flights from Toronto to Chicago by exploring options for tickets at noon.

Cheap flights from Toronto to Chicago in October, November 2020

The best prices found for YTO to CHI flights for October, November
25 Nov - 28 Nov
C$ 266pp
YYZ
Toronto Pearson Intl
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YYZ
Toronto Pearson Intl
13 Nov - 13 Nov
C$ 282pp
YYZ
Toronto Pearson Intl
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YYZ
Toronto Pearson Intl
2 Nov - 6 Dec
C$ 295pp
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

Toronto to Chicago 2020 flight deals

Cheap flights to Chicago from Toronto found for this year
25 Nov - 28 Nov
C$ 266pp
YYZ
Toronto Pearson Intl
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YYZ
Toronto Pearson Intl
12 Dec - 15 Dec
C$ 274pp
YYZ
Toronto Pearson Intl
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
 
1 STOP
YYZ
Toronto Pearson Intl
13 Nov - 13 Nov
C$ 282pp
YYZ
Toronto Pearson Intl
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YYZ
Toronto Pearson Intl

Direct flights to Chicago from Toronto

Save time with Toronto to Chicago direct flight deals
26 Feb - 1 Mar
C$ 255pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
26 Feb - 1 Mar
C$ 258pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
26 Feb - 1 Mar
C$ 263pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl

Last minute flights from Toronto to Chicago

Late deals on round-trip flights to Chicago from Toronto, departing today and this week
31 Oct - 2 Nov
C$ 300pp
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
31 Oct - 2 Nov
C$ 304pp
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
31 Oct - 2 Nov
C$ 307pp
YYZ
Toronto Pearson Intl
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
   
2 STOPS
YYZ
Toronto Pearson Intl

One-way flights to Chicago from Toronto

The cheapest one-way flights from Toronto to Chicago
10:55 a.m. - 11:45 a.m.
Porter Airlines
Direct
1h 50m
YTZ - MDW
Porter Airlines
C$ 162
KAYAK
2:30 p.m. - 3:51 a.m.
Air Canada
1 stop
14h 21m
YYZ - ORD
Air Canada
C$ 207
mytrip.com
1:30 a.m. - 8:03 a.m.
Delta
2 stops
7h 33m
YYZ - MDW
Delta
C$ 219
Delta

Related info for your journey

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

Flight FAQs

From Toronto to Chicago

Can I find flights from Toronto to Chicago for under C$ 263 on Cheapflights?

Yes, there are multiple flights from Toronto to Chicago for under C$ 263. The cheapest flight booked recently is on Air Canada for just C$ 246, but on average you can expect to pay C$ 274.

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

Airlines globally have implemented additional safety measures to accommodate you. Delta is one of them. Airline carriers are regularly disinfecting and sanitizing their aircraft. Masks are provided and are mandatory while on board. Pre-flight testing for symptoms and antibodies, alongside socially-distanced seating (for a limited time) will work towards keeping travellers safer while flying from Toronto to Chicago. Policies will vary by airline.

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

Air Canada, American Airlines, and United Airlines are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Are there direct flights from Toronto to Chicago for under C$ 263 on Cheapflights?

Cheapflights has 20 direct flights from Toronto to Chicago under C$ 263. A good price for a direct flight from Toronto to Chicago is less than C$ 290.

Are there last-minute flights available from Toronto to Chicago for under C$ 395?

There are currently 20+ open flights from Toronto to Chicago within the next 7 days for less than C$ 395.

What days are direct flights available from Toronto to Chicago?

Days when direct flights are available for this flight are: Sunday, Friday, Saturday.

How many flights depart from Toronto to Chicago on average per day?

Per day, 3 flights depart from Toronto to Chicago on average.
Morning (6am - Noon) - 67% of flight departures
Afternoon (Noon - 6pm) - 33% of flight departures

Is Toronto weather warmer or cooler than Chicago?

With an average temperature of 29 °C, peak weather can be found in July. As a traveller, expect to see changes in flight prices during that period. The temperatures in Chicago are hotter than in Toronto.

How long is the flight from Toronto to Chicago?

Departing from Toronto to Chicago will take you 1h 41m. The distance between Toronto and Chicago is about 703 km. Most flights are nonstop.

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

Air Canada, at C$ 247, was found to be the cheapest airline from Toronto to Chicago.Alternate airlines to your destination round-trip include Porter Airlines and United Airlines. Air Canada is 25% cheaper than the average price of flights available within the next 90 days to this destination.

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

The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as C$ 158. However, be on the lookout for offers from Porter Airlines and American Airlines, as they are both options that can get you from Toronto to Chicago for a low price.

Destination information for Chicago

Things to know before you go. Useful info for your trip from Toronto 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 Toronto

Billy Bishop Toronto City Airport (YTZ)
Kitchener (YKF)
Hamilton (YHM)

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Hourly flight availability from Toronto to Chicago

Morning 6 AM to noon 68% of YTO to US-CHI departures
Afternoon Noon to 6 PM 32% of YTO to US-CHI departures
Early morning Midnight to 6 AM 0% of YTO to US-CHI departures
Evening 6 PM to midnight 0% of YTO to US-CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Toronto to Chicago
Sunday
17 daily flights
Monday
16 daily flights
Tuesday
13 daily flights
Wednesday
9 daily flights
Thursday
17 daily flights
Friday
17 daily flights
Saturday
13 daily flights
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