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Flights Toronto — Chicago

Toronto
YTO
Chicago
CHI

Cheap flights Toronto — Chicago

Below you can see the best deals on flights Toronto — Chicago for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 3 July, from AED 526.

Top 10 cheap flights Toronto — Chicago

Direct flights Toronto — Chicago

Direct flight options for Toronto — Chicago with no stopovers on upcoming dates. A direct flight is faster and more convenient — especially when travelling with luggage or children.

The fastest direct flight is operated by Air Transat — travel time is 1 h 50 min.

Top 10 direct flights Toronto — Chicago

About the Toronto — Chicago flight

On this page, you can book flights from Toronto to Chicago. The direct distance between the cities is 703 km, and flight frequency reaches 265 flights per week, providing a wide selection of departure times.

Flights are operated by airlines such as United Airlines, Air Canada, and American Airlines. Prices are dynamic, so we recommend using the low-fare calendar and checking information in advance on how to get to Toronto airport and how to get from Chicago airport to your destination.

Flight schedule Toronto — Chicago

The table shows direct flights Toronto → Chicago on the selected date. The flight takes approximately 1 h 50 min. Regular flights are operated by Air Canada, United Airlines, Porter Airlines and American Airlines. Departures from Pearson International Airport, Billy Bishop Toronto City Airport and Hamilton Airport airports, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

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Flight ticket prices by day: Toronto — Chicago

Below is a calendar of the lowest flight ticket prices for Toronto — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from AED 519 in F, and the most expensive are around AED 706 in n. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Toronto → Chicago, average one-way price

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
JanAED 552lowMayAED 677mediumSepAED 702medium
FebAED 527lowJunAED 802highOctAED 652medium
MarAED 577lowJulAED 852highNovAED 602low
AprAED 627mediumAugAED 827highDecAED 777high

Some values are estimated based on seasonality.

When to fly

Weather conditions in Chicago are most favorable in July and August, when the average high is 26.5°C. The coldest months are January and February with temperatures as low as -5°C, while peak precipitation occurs in May.

The most budget-friendly flights are available in September with prices starting AED 519. The most expensive period for travel is March, when the minimum ticket cost increases to AED 706.

The optimal time to book is September or October: during this period, the weather remains comfortable, and prices are among the lowest of the year. It is recommended to avoid the winter months due to the risk of flight delays caused by weather conditions.

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

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How to get the best deal on a Toronto — Chicago ticket

  • Consider departing from different airports: flights from Billy Bishop (YTZ) are often more convenient for those who value proximity to the city center, while the main hub, Pearson (YYZ), offers the maximum number of options.
  • Use the low-fare calendar on this page to find dates with tickets starting AED 519, as flight costs can vary significantly even within a single week.
  • Since the flight time is less than an hour and a half, legacy carriers like UA and AC often compete with low-cost airlines, offering comparable prices on basic fares.
  • To lock in a great price, book your tickets 4–6 weeks before departure, especially if your trip falls on a weekend or a public holiday.

Airlines

Ten airlines operate on the Toronto—Chicago route, with United Airlines, Air Canada, and American Airlines leading in flight frequency. Flights are primarily direct, providing up to 265 flights per week. You can check the detailed schedule and choose a suitable option by day of the week in the interactive list below.

  • Air Canada
    Air CanadaAC
    91x/week
    WebsiteFleet: 20346M pax/year
    • Direct flight YYZ → ORD82x/week
      Duration
      1h 58m
      Days
      un,MonS
    • Direct flight YTZ → ORD9x/week
      Duration
      1h 56m
      Days
      un,MonS
  • United Airlines
    United AirlinesUA
    77x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight YYZ → ORD67x/week
      Duration
      1h 59m
      Days
      un,MonS
    • Direct flight YTZ → ORD9x/week
      Duration
      1h 56m
      Days
      un,MonS
  • Porter Airlines
    Porter AirlinesPD
    31x/week
    WebsiteFleet: 714.5M pax/year
    • Direct flight YYZ → ORD23x/week
      Duration
      2h 6m
      Days
      un,MonS
    • Direct flight YTZ → MDW8x/week
      Duration
      1h 50m
      Days
      un,MonS
  • American Airlines
    American AirlinesAA
    20x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight YYZ → ORD20x/week
      Duration
      2h 4m
      Days
      un,MonS
  • All Nippon Airways
    All Nippon AirwaysNH
    13x/week
    WebsiteFleet: 21648M pax/year
    • Direct flight YYZ → ORD13x/week
  • Air Transat
    Air TransatTS
    9x/week
    WebsiteFleet: 405M pax/year
    • Direct flight YTZ → MDW9x/week
      Duration
      1h 50m
      Days
      un,MonS
  • Alaska Airlines
    Alaska AirlinesAS
    9x/week
    WebsiteFleet: 31545M pax/year
    • Direct flight YYZ → ORD9x/week
      Duration
      1h 58m
      Days
      un,MonS
  • Japan Airlines
    Japan AirlinesJL
    7x/week
    WebsiteFleet: 14540M pax/year
    • Direct flight YYZ → ORD7x/week
  • British Airways
    British AirwaysBA
    5x/week
    WebsiteFleet: 29243M pax/year
    • Direct flight YYZ → ORD5x/week
      Duration
      1h 58m
      Days
      un,MonS
  • Iberia
    IberiaIB
    3x/week
    WebsiteFleet: 9224M pax/year
    • Direct flight YYZ → ORD3x/week
      Duration
      2h 5m
      Days
      un,MonS

Cities and airports on the Toronto — Chicago route

Flights Toronto — Chicago depart from Pearson International Airport, Billy Bishop Toronto City Airport, Hamilton Airport and Region of Waterloo International Airport and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure airports
Arrival airports

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Frequently asked questions about the Toronto — Chicago flight

How long is the flight from Toronto to Chicago?

The average travel time for a direct flight is between 1 hour 20 minutes and 1 hour 40 minutes, given the route distance of 703 km.

Which airlines operate flights on this route?

Major carriers such as United Airlines, Air Canada, and American Airlines operate on this route, along with regional airlines including Porter Airlines.

Are there direct flights between the cities?

Yes, there are approximately 265 direct flights per week on this route, making it easy to find a convenient departure time throughout the day.

When is the best time to buy tickets to save money?

The best deals are usually available when booking 1–2 months before the trip. The current minimum for this season starts from 10,346 ₽.

Which airport do flights from Toronto arrive at?

Most flights arrive at Chicago's major international airports — O'Hare (ORD) and Midway (MDW).