Cheap flights from Toronto to Chicago

One-way fares from $229 · YTO → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → Toronto
Cheapest fare
$229

Air Canada · Fri, Nov 20

Cheapest month
November

from $229

Direct flights
Yes

Porter Airlines Canada, American Airlines, United Airlines + 1 more

Flight time
2h 03m

700 km

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Cheapest month to fly from Toronto to Chicago

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

  1. November 2026 Cheapest $229

Cheapest dates in November 2026

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

Air Canada
Depart08:30 Fri, Nov 20YTZ → ORD 4h 06m · 1 stop
$229one way, per person
View deal
Porter Airlines Canada
Depart16:35 Wed, Nov 18YTZ → ORD 2h 05m · Direct
$237one way, per person
View deal
Porter Airlines Canada
Depart10:29 Sun, Nov 15YTZ → ORD 2h 05m · Direct
$240one way, per person
View deal
Porter Airlines Canada
Depart10:29 Fri, Nov 27YTZ → ORD 2h 05m · Direct
$247one way, per person
View deal
American Airlines
Depart18:21 Sat, Nov 7YYZ → ORD 2h 20m · Direct
$256one way, per person
View deal
American Airlines
Depart18:21 Mon, Nov 9YYZ → ORD 2h 20m · Direct
$261one way, per person
View deal
Flair Airlines
Depart07:35 Thu, Nov 12YYZ → ORD 6h 52m · 1 stop
$261one way, per person
View deal
United Airlines
Depart06:45 Sat, Nov 14YYZ → ORD 2h 09m · Direct
$268one way, per person
View deal
See every date in November 2026 →

Plan the rest of your trip to Chicago

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

Where to stay

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Things to do

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

Getting around

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

Stay connected

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About flights from Toronto to Chicago

Toronto (YTO) and Chicago (CHI) are about 700 km apart. Direct flights take around 2h 03m, and recent direct fares were with Porter Airlines Canada, American Airlines, United Airlines and Air Canada. Over the next few months, one-way fares start from $229, 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 Toronto to Chicago?

The cheapest one-way fare we've seen recently is $229 with Air Canada, departing Friday, November 20, 2026.

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

November 2026 currently has the lowest fares, from $229 one way.

Are there direct flights from Toronto to Chicago?

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

How long is the flight from Toronto to Chicago?

A direct flight takes about 2h 03m. Toronto and Chicago are around 700 km apart.

Which airlines fly from Toronto to Chicago?

Recent fares on this route were with Air Canada, Porter Airlines Canada, American Airlines, Flair Airlines and United Airlines.

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