Cheap flights from Chicago to Toronto

One-way fares from $99 · CHI → YTO · prices found by travellers in the last 48 hours

Compare all dates Toronto → Chicago
Cheapest fare
$99

Porter Airlines Canada · Tue, Nov 3

Cheapest month
November

from $99

Direct flights
Yes

Porter Airlines Canada and United Airlines

Flight time
1h 40m

700 km

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Cheapest month to fly from Chicago to Toronto

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 Cheapest $99
  2. December 2026 $148
  3. April 2027 $143

Cheapest dates in November 2026

The lowest fares we've seen for each day, cheapest first.

Porter Airlines Canada
Depart20:45 Tue, Nov 3ORD → YYZ 2h 01m · Direct
$99one way, per person
View deal
Porter Airlines Canada
Depart12:15 Thu, Nov 12ORD → YTZ 1h 45m · Direct
$130one way, per person
View deal
Porter Airlines Canada
Depart12:15 Mon, Nov 16ORD → YTZ 1h 45m · Direct
$141one way, per person
View deal
Porter Airlines Canada
Depart12:15 Wed, Nov 25ORD → YTZ 1h 45m · Direct
$143one way, per person
View deal
Porter Airlines Canada
Depart12:15 Sun, Nov 15ORD → YTZ 1h 45m · Direct
$148one way, per person
View deal
Porter Airlines Canada
Depart18:20 Fri, Nov 27ORD → YTZ 1h 45m · Direct
$152one way, per person
View deal
Porter Airlines Canada
Depart18:20 Sun, Nov 22ORD → YTZ 1h 45m · Direct
$222one way, per person
View deal
United Airlines
Depart07:03 Fri, Nov 20ORD → YYZ 1h 44m · Direct
$249one way, per person
View deal
See every date in November 2026 →

Plan the rest of your trip to Toronto

Where to stay, what to do and getting around, from our travel partners.

Where to stay

Hotels in TorontoCompare places to stay on Booking.com Find hotels →

Things to do

Things to do in TorontoTours, attractions and day trips on Klook Explore →

Getting around

Airport transfer in TorontoPre-book a driver to meet you at arrivals, with Kiwitaxi Book a transfer → Car hire in TorontoCompare rental cars from major brands on EconomyBookings Compare cars →

Stay connected

eSIM for CanadaMobile data from the moment you land, by Airalo Get eSIM →

About flights from Chicago to Toronto

Chicago (CHI) and Toronto (YTO) are about 700 km apart. Direct flights take around 1h 40m, and recent direct fares were with Porter Airlines Canada and United Airlines. Over the next few months, one-way fares start from $99, and November 2026 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from Chicago to Toronto?

The cheapest one-way fare we've seen recently is $99 with Porter Airlines Canada, departing Tuesday, November 3, 2026. Over the coming months, the lowest fare in each month ranges from $99 to $148.

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

November 2026 currently has the lowest fares, from $99 one way.

Are there direct flights from Chicago to Toronto?

Yes. Recent direct fares were with Porter Airlines Canada and United Airlines.

How long is the flight from Chicago to Toronto?

A direct flight takes about 1h 40m. Chicago and Toronto are around 700 km apart.

Which airlines fly from Chicago to Toronto?

Recent fares on this route were with Porter Airlines Canada and United Airlines.

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