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Flights from Toronto to Chicago

Airlines operating flights from Toronto to Chicago

Choose from 3 airlines flying from Toronto to Chicago, including Air Canada, Porter Airlines and American Airlines. Porter Airlines currently offers the cheapest ticket on this route.
Air Canada logo Air Canada
Porter Airlines logo Porter Airlines
American Airlines logo American Airlines
Airlines are determined based on actual purchased flight tickets from Toronto to Chicago according to previous 12 months data from Trip.com.

Find the cheapest direct flight options from Toronto to Chicago over the next three months. Book one-way tickets from £76 and round-trip tickets from £121.

Displayed flight fares from Toronto to Chicago are based on average prices across airlines for the next 3 months, according to the latest Trip.com database.

Flight details for Toronto to Chicago

The distance between Toronto and Chicago is 701.97km. It takes around 2 hours on average to fly from Toronto to Chicago. Based on Trip.com's data, travel demand peaks in July. The off-season for travel is September.

Cheapest one-way flight price£76
Cheapest return ticket price£121
Off-season travel monthSeptember
Peak season for travelJuly
Flight distance701.97km
Average flight time2 hours
Popular airlineAir Canada
Flight statistics for the Toronto–Chicago route are based on aggregated booking data from Trip.com over the past 12 months.

Trip.com price insights on flights from Toronto to Chicago

What is the cheapest month for one-way flights from Toronto to Chicago?

The average one way ticket price paid by Trip.com users from Toronto to Chicago in each month over the past 12 months.

Based on Trip.com data, the cheapest month to fly from Toronto to Chicago is June, with an average price of £124. The most expensive month is usually October, with average prices reaching £177.

£177
£151
£124
£98
    Cheapest
  • £126
    Mar
  • £135
    Apr
  • £126
    May
  • £124
    Jun
  • £130
    Jul
  • £155
    Aug
  • £138
    Sep
  • £177
    Oct
  • £164
    Nov
  • £157
    Dec
  • £135
    Jan
  • £139
    Feb

What is the cheapest month for return flights from Toronto to Chicago?

Average price of return flights from Toronto to Chicago purchased by Trip.com users by month over the past 12 months

Based on Trip.com's historical data, March is often the cheapest month for fly from Toronto to Chicago, with an average price of £169. October is usually the most expensive period, with prices averaging as high as £240.

£240
£205
£169
£134
  • £169
    Mar
  • £178
    Apr
  • £189
    May
  • £183
    Jun
  • £184
    Jul
  • £197
    Aug
  • £171
    Sep
  • £240
    Oct
  • £220
    Nov
  • £219
    Dec
  • £198
    Jan
  • £189
    Feb

Which day of the week is cheapest to fly from Toronto to Chicago?

Data is based on the past 12 months and shows the average weekly airfare from Toronto to Chicago on different days of the week according to Trip.com.

Based on Trip.com data from the past 12 months, the cheapest day to fly from Toronto to Chicago is Saturday. The average fare on this day is usually lower than on other days. Try to avoid flying on Friday as fares are usually the highest.

£153
£144
£135
£126
    Cheapest
  • £139
    Mon
  • £138
    Tue
  • £142
    Wed
  • £142
    Thu
  • £153
    Fri
  • £135
    Sat
  • £150
    Sun

During the St Patrick's Day, which day is cheapest to fly from Toronto to Chicago?

Data is based on the lowest one-way price from Toronto to Chicago during St Patrick's Day in the Trip.com database over the past three days.

During the St Patrick's Day, flights from Toronto to Chicago are cheapest on Mar 18, with the lowest price of £102.

£336
£219
£102
0
    Cheapest
  • £336
    Mar 13
  • £308
    Mar 14
  • £106
    Mar 15
  • £212
    Mar 16
  • £232
    Mar 17
  • £102
    Mar 18
  • £228
    Mar 19

Flight FAQs

  • Which airlines offer the cheapest flights from Toronto (YTO) to Chicago (CHI)?

    Based on Trip.com data, Porter Airlines offers one-way fares as low as £76 on Cheapest nonstop routes (e.g. YTZ to MDW on Sun, Apr 19), while Porter Airlines offers Cheapest nonstop round-trips from £121 departing on Sat, May 2 and returning on Sat, May 9.
  • At the moment, you can catch a direct flight from Toronto to Chicago with the following airlines, including: Air Canada Porter Airlines American Airlines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.
  • It takes about 2 hours to fly from Toronto (YTO) to Chicago (CHI).
  • By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Toronto to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.
  • Based on Trip.com data in the past 4 weeks, there is 153 flight per week flying from Toronto to Chicago. You can check the weekly schedule for popular airlines on this route below: Air Canada: S/M/T/W/T/F/S -- AC5141 (07:23) Air Canada: S/M/T/W/T/F/S -- AC5143 (08:58)
  • To find best deals on flights from Toronto to Chicago, you can use various tools on Trip.com:
    · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Sun, Apr 19, with one-way flights priced at just £76.
    · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Porter Airlines.
    · Set up price alerts to easily monitor ticket prices without having to check every day.
    · Check Trip.com flight deals and promo codes frequently.
    · Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around July.
    · Get exclusive promo codes for Trip.com app users.
  • The cheapest months to fly from Toronto to Chicago is September, when demand for travel is lower.
  • After crunching the numbers on our March flight calendar, it's currently cheapest to fly from Toronto to Chicago on March 28, 2026 with Porter Airlines, with prices starting at £76.
  • You can land at any one of the following hubs in Chicago, with Toronto Pearson International Airport to O'Hare International Airport (YYZ-ORD) is by far the most common option on this route: Midway International Airport (MDW) O'Hare International Airport (ORD) Chicago Rockford International Airport (RFD).
  • The time difference between Chicago and Toronto is 1h.
  • Tickets can only be changed or cancelled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.

Trip.com airline insights on flights from Toronto to Chicago

Which airlines offer the cheapest direct flights from Toronto to Chicago?

Data is based on the past 12 months and reflects the average fare of all direct flights from Toronto to Chicago on Trip.com.

Based on Trip.com data from the past 12 months, the airline offering the cheapest direct flights from Toronto to Chicago is Porter Airlines, with an average fare of £157.

£146
£157
£169
£180
£191
Porter Airlines
£157
Porter Airlines
WestJet
£163
WestJet
United Airlines
£164
United Airlines
Air Canada
£174
Air Canada
Air Transat
£176
Air Transat
American Airlines
£191
American Airlines

Which airlines operate the most flights from Toronto to Chicago?

The data is based on the past month and shows the number of flights each airline has from Toronto to Chicago on Trip.com.

According to Trip.com data from the past month, the airline with the most flights from Toronto to Chicago is Air Canada, operating 80 flights per week.

16
37
59
80
Air Canada
80
Air Canada
United Airlines
79
United Airlines
Air New Zealand
45
Air New Zealand
Porter Airlines
43
Porter Airlines
Qantas Airways
37
Qantas Airways
Alaska Airlines
37
Alaska Airlines

How many flights fly from Toronto to Chicago each day?

The data is based on the past month and shows the number of flights per day of the week from Toronto to Chicago on Trip.com.

Based on Trip.com data from the past month, flights from Toronto to Chicago are most frequent on Friday, while the fewest flights operate on Tuesday.

311
275
239
203
Highest
252
Mon
239
Tue
242
Wed
250
Thu
311
Fri
271
Sat
302
Sun

Note: Prices shown on this page are the estimated lowest prices and include all taxes and fees found in the last 24 hours.

Book with no extra fees

Prices displayed on this page are all-inclusive (including taxes, fuel surcharges, civil aviation development fund, etc.), with all fees confirmed before payment. Fees for luggage, meals, Wi-Fi, or other additional services are also included as shown in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page have been updated within the last 24 hours—sometimes even in real time. The more popular the route, the more accurate the data.

Change & Cancellation Policy

Trip.com shows the cancellation and change policies for each flight ticket during the booking process, including any fees and applicable conditions. Please check the following scenarios:
Voluntary cancellation/change:
To request a change or cancellation, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and flight segment, and submit your request. Please note that additional charges may apply according to the airline's ticket policy.
Cancellation/change due to a flight schedule change:
If the flight schedule has changed and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please visit the customer support pages.