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Cheap flights from Toronto to Chicago

One-way from $129, found by travellers in the last 7 days. Aviasales checks the live price.

Departure
Return
Prices for nearby dates
Tue, Oct 13$254Wed, Oct 14$185Thu, Oct 15Any priceFri, Oct 16$129Sat, Oct 17Any priceSun, Oct 18Any priceMon, Oct 19Any priceTue, Oct 20Any price

Cheapest one-way tickets

Recent finds on different dates, for 1 adult. Baggage and fare rules are shown on Aviasales, where the price is checked live.

Cheapest
$129
Air Canada, flight AC 8547Found yesterday, 1 adult
Check price on Aviasales
12:15pmTorontoFri, Oct 16
Travel time 2h 10m, nonstopYTZORD
1:25pmChicagoFri, Oct 16
$185
Porter Airlines Canada, flight PD 2387Found 5 days ago, 1 adult
Check price on Aviasales
10:10amTorontoWed, Oct 14
Travel time 1h 50m, nonstopYTZMDW
11:00amChicagoWed, Oct 14
$187
United Airlines, flight UA 5874Found 4 days ago, 1 adult
Check price on Aviasales
9:00pmTorontoTue, Oct 6
Travel time 2h 6m, nonstopYYZORD
10:06pmChicagoTue, Oct 6
$209
Air Canada, flight AC 7958Found 7 days ago, 1 adult
Check price on Aviasales
10:45amTorontoSun, Nov 22
Travel time 4h 8m, 1 stopYTZORD
1:53pmChicagoSun, Nov 22
$210
American Airlines, flight AA 3524Found 7 days ago, 1 adult
Check price on Aviasales
7:09amTorontoFri, Nov 20
Travel time 2h 30m, nonstopYYZORD
8:39amChicagoFri, Nov 20

Round trips

The cheapest return tickets found recently, price for the whole trip.

Plan the rest of the trip

  • Mobile data in United StatesTravel eSIM from $4, installed before you fly.
    Compare plans
  • Getting from the airportTransfers and car hire in Chicago, booked ahead at a fixed price.
    See options
  • Things to do in ChicagoPopular tours from $27.95 per person.
    See ideas
  • Travel insuranceTravel insurance quotes for United States from EKTA; check what each policy covers.
    Get a quote
  • Flight delayed?Delayed 3+ hours or cancelled for a reason within the airline’s control? Up to CA$1,000 per person under Canada’s rules.
    Check

Price calendar

The lowest one-way fare found for each day over the next 60 days. A dash means no recent fare; you can still pick that day.

October 2026

MoTuWeThFrSaSu1234–5$2966$1877–8$2309$27510–11–12$29313$25414$18515–16$12917–18–19–20–21–22–23–24–25–26–27–28–29–30–31–

November 2026

MoTuWeThFrSaSu1–2–3–4–5–6–7–8–9–10–11–12–13–14–15–16–17–18–19–20$21021–22$20923–24–25–26–27–28–29–30–

December 2026

MoTuWeThFrSaSu1–2–345678910111213141516171819202122232425262728293031
$187 or lessGreen: the cheapest fifth of fares on this route. Lowest in these 60 days: Oct 16, $129.

Lowest fares by month

In the fares found this week, October has the lowest: from $129 one-way, against $212 in April 2027. Pick a month to see its cheapest date.

$0$100$200$300$129OctNovDecJanFebMarAprMayJunJulAugSep
Show as a table
MonthCheapest one-wayDateStops
October$129Fri, Oct 16Nonstop
November$209Sun, Nov 22Nonstop
December—
January 2027—
February 2027—
March 2027—
April 2027$212Thu, Apr 8Nonstop
May 2027—
June 2027—
July 2027—
August 2027—
September 2027—

Questions travellers ask

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

In the fares found this week, October has the lowest: from $129 one-way, against $212 in April 2027.

Are there direct flights from Toronto to Chicago?

Yes. Recent fares include nonstop flights with Porter Airlines Canada, American Airlines, Air Canada and United Airlines.

How long is the flight from Toronto to Chicago?

A nonstop flight takes about 1h 50m. The distance is 446 mi.

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