Cheap flights from Toronto to Chicago

Toronto
YTO
Chicago FSS
CHI

Flight deals from Toronto to 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 23 September, from $123.

Top 10 cheap flights from Toronto to Chicago

PD
$ 133

Toronto — Chicago

10:10—11:00
14 Sep 2026
1 h 50 m
Direct flight
PD
$ 133

Toronto — Chicago

13:45—14:35
14 Sep 2026
1 h 50 m
Direct flight
PD
$ 133

Toronto — Chicago

10:10—11:00
13 Sep 2026
1 h 50 m
Direct flight
PD
$ 135

Toronto — Chicago

13:45—14:35
8 Sep 2026
1 h 50 m
Direct flight
PD
$ 135

Toronto — Chicago

10:10—11:00
8 Sep 2026
1 h 50 m
Direct flight
PD
$ 135

Toronto — Chicago

13:45—14:35
5 Sep 2026
1 h 50 m
Direct flight
PD
$ 135

Toronto — Chicago

10:10—11:00
5 Sep 2026
1 h 50 m
Direct flight
PD
$ 135

Toronto — Chicago

10:10—11:00
10 Sep 2026
1 h 50 m
Direct flight
PD
$ 135

Toronto — Chicago

13:45—14:35
10 Sep 2026
1 h 50 m
Direct flight
PD
$ 135

Toronto — Chicago

10:10—11:00
12 Sep 2026
1 h 50 m
Direct flight

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Toronto — Chicago flight

Looking for cheap flights from Toronto to Chicago? Compare fares from different airlines, check the flight schedule and travel time — and book your Toronto — Chicago ticket online at the best price.

The route has direct flights — around 796 flights per week, flights are operated by Air Canada, United Airlines, Porter Airlines, American Airlines and 6 more airlines, a nonstop flight takes about 1 h 50 min, the distance between the cities is around 703 km.

Planning your trip? You may find our Chicago travel guide, how to get from the airport into town and Chicago weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from $123Min. price
SeptemberCheapest
JunePeak season
YesDirect flights
703 kmDistance
1 h 50 minTravel time
10Airlines
796 / wkFlights

Flight schedule from Toronto to Chicago

The table shows direct flights from Toronto to 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.

Today
Any time
Last update: 14 Aug 2026

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 $123 in September, and the most expensive are around $186 in June. 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

Average one-way fares from Toronto to Chicago by month. Tickets are usually cheapest in February (around $127) and priciest in July (about $205) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$133lowMay$163mediumSep$169medium
Feb$127lowJun$193highOct$157medium
Mar$139lowJul$205highNov$145low
Apr$151mediumAug$199highDec$187high

Some values are estimated based on seasonality.

When to fly

Weather in Chicago: it is warmest in July (up to 27 °C on average) and coolest in January (around 0 °C). The driest month is November.

Tickets are usually cheapest in September and most expensive in June. Compare prices and weather by month in the charts below to pick the best time to fly.

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

  • Book ahead: fares for Toronto — Chicago are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • Toronto is served by more than one airport — compare fares and travel time to each before you book.
  • The cheapest month to fly to Chicago is usually September — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the Toronto — Chicago route are operated by 10 airlines; Air Canada runs the most flights (around 34% of all flights). Compare carriers, flight shares and schedules below.

  • Air CanadaAC
    91x/week
    WebsiteFleet: 20346M pax/year
    • Direct flight YYZ → ORD82x/week
      Duration
      1h 58m
      Days
      MTWTFSS
    • Direct flight YTZ → ORD9x/week
      Duration
      2h 6m
      Days
      MTWTFSS
    34.4%Open →
  • United AirlinesUA
    77x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight YYZ → ORD67x/week
      Duration
      2h
      Days
      MTWTFSS
    • Direct flight YTZ → ORD9x/week
      Duration
      1h 57m
      Days
      MTWTFSS
    28.9%Open →
  • Porter AirlinesPD
    31x/week
    WebsiteFleet: 714.5M pax/year
    • Direct flight YYZ → ORD23x/week
      Duration
      2h 6m
      Days
      MTWTFSS
    • Direct flight YTZ → MDW8x/week
      Duration
      1h 50m
      Days
      MTWTFSS
    11.6%Open →
  • American AirlinesAA
    20x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight YYZ → ORD20x/week
      Duration
      2h 5m
      Days
      MTWTFSS
    7.7%Open →
  • All Nippon AirwaysNH
    13x/week
    WebsiteFleet: 21648M pax/year
    • Direct flight YYZ → ORD13x/week
      Duration
      2h 2m
      Days
      MTWTFSS
    4.9%Open →
  • Air TransatTS
    9x/week
    WebsiteFleet: 405M pax/year
    • Direct flight YTZ → MDW9x/week
      Duration
      1h 50m
      Days
      MTWTFSS
    3.5%Open →
  • Alaska AirlinesAS
    9x/week
    WebsiteFleet: 31545M pax/year
    • Direct flight YYZ → ORD9x/week
    3.3%Open →
  • Japan AirlinesJL
    7x/week
    WebsiteFleet: 14540M pax/year
    • Direct flight YYZ → ORD7x/week
      Duration
      1h 55m
      Days
      MTWTFSS
    2.5%Open →
  • British AirwaysBA
    5x/week
    WebsiteFleet: 29243M pax/year
    • Direct flight YYZ → ORD5x/week
      Duration
      1h 55m
      Days
      MTWTFSS
    2.0%Open →
  • IberiaIB
    3x/week
    WebsiteFleet: 9224M pax/year
    • Direct flight YYZ → ORD3x/week
      Duration
      1h 55m
      Days
      MTWTFSS
    1.3%Open →

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

Toronto

YTO
Canada
About the cityHow to get thereWeatherAll about the country Canada
Arrival

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
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?

A nonstop Toronto — Chicago flight takes about 1 h 50 min — the distance between the cities is around 703 km.

How far is it from Toronto to Chicago?

The distance from Toronto to Chicago is about 703 km, which a nonstop flight covers in around 1 h 50 min.

Are there direct flights from Toronto to Chicago?

Yes, there are nonstop flights Toronto — Chicago — around 796 flights per week.

Which airlines fly from Toronto to Chicago?

Airlines operating Toronto — Chicago include Air Canada, United Airlines, Porter Airlines, American Airlines, All Nippon Airways. See the full list with schedules in the "Airlines" section on this page.

Which airports do Toronto — Chicago flights use?

Flights from Toronto depart from Pearson International Airport, Billy Bishop Toronto City Airport, Hamilton Airport, and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Toronto to Chicago?

The price of a Toronto — Chicago ticket depends on your travel date, season and demand: it is usually cheapest to fly in September, and most expensive in June. Tickets typically cost between $123 and $186. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Toronto — Chicago?

Flights Toronto — Chicago are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is September. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Toronto to Chicago?

To catch a low fare Toronto — Chicago, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually September.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from Toronto

See all
New York CityMontrealOttawaVancouverCalgaryHalifaxWashington, D.C.EdmontonDetroitWinnipegBostonLondonAtlantaSt. John'sQuebec CityMinneapolisPhiladelphiaSaskatoonThunder BayOrlandoCancunMonctonCharlotteLos AngelesSan FranciscoDallasReginaLas VegasKelownaNashvilleCharlottetownFort LauderdaleTampaMexico CityLondonVictoriaDublinFrankfurt am MainPunta CanaCleveland

Where else you can fly from Chicago

See all
New York CityDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverLondonNashvilleIndianapolisSan DiegoMontrealSt. LouisMilwaukeeCharlottePhiladelphiaColumbusKansas CityMiamiPhoenixLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochesterCleveland

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