Cheap flights from Toronto to Chicago
from 108 US$

From 180 USD — compare hundreds of airlines

We search 100+ flight sitesDirect flights~1h 23mReturn route: Chicago → Toronto

The cheapest month is usually 2026-09 · 108 US$

Live fares from 100+ sites — free, with no hidden fees.

About this route

Compare flights from Toronto to Chicago, a about 701 km route (around 1h 23m nonstop). We gather live prices from hundreds of airlines and agencies so you can find the cheapest and book on the official site, with no hidden fees. Direct flights are available. Airlines such as American Airlines, Air Canada, Etihad Airways operate this route.

Nonstop time

1h 23m

Distance

701 km

Stops

Nonstop

Airlines

The airports on this route

Toronto

Toronto Pearson International AirportYYZ

About 22 km from downtown Toronto

Getting around: UP Express train to Union Station, buses, taxis and apps

The UP Express reaches Union Station in ~25 min — it nearly always beats traffic.

When to buy and when to fly

Prices by date

Fares found by date — cheapest days in green.

See prices for my dates →

109 US$

11/09

109 US$

12/09

108 US$

13/09

How to get the best price

1The sticker price is real — but it moves fastLow fares last hours or days. If the number works, search it today; waiting rarely improves it.

2Buy 4–8 weeks aheadThat window usually holds the best fares; holidays call for even more margin.

3Flexibility = moneyShifting departure 2–3 days can move the fare 100+ US$. Tuesdays and Wednesdays tend to be cheap.

Airlines on this route

American Airlines Air Canada Etihad Airways Iberia Porter Airlines Canada United Airlines WestJet

FAQ

What's the cheapest month to fly Toronto to Chicago?

It's usually 2026-09, from 108 USD. Use the price calendar to compare other dates.

How long is the flight from Toronto to Chicago?

A nonstop flight takes about 1h 23m and covers around 701 km. Connecting itineraries take longer.

Are there direct flights from Toronto to Chicago?

Yes, this route has nonstop flights. Filter by "nonstop" to see them.

Which airlines fly from Toronto to Chicago?

American Airlines, Air Canada, Etihad Airways, Iberia operate this route, among others. Compare them all in the results.

When should I book Toronto–Chicago flights?

As a rule of thumb, booking 3–8 weeks ahead and avoiding weekends and holidays tends to give the best prices. Use the calendar to spot the cheapest dates.