Toronto to Chicago flights
Round trip · Economy · Prices per person in USD
Prices updated
Prices are typical right now
$278 is close to the usual $284 for Toronto → Chicago.
Buy now or wait? We're still learning this route. We have 1 day of prices so far and need about a week to say whether to book or wait.
Not ready to book? Get an email when Toronto → Chicago drops below your price.Cheapest round trip by month
Lowest fare found per departure month| Month | Cheapest round trip |
|---|---|
| September 2026 | No fares found yet |
| October 2026 | $280 |
| November 2026 | $278 (cheapest month) |
| December 2026 | No fares found yet |
| January 2027 | No fares found yet |
| February 2027 | No fares found yet |
| March 2027 | $380 |
Cheapest dates in the next 4 months
Round trip, per person-
Nov 18 – 27 9 nights · leave Wed$278$278 Book
Porter Airlines Canada Nonstop · 2h 05m -
Oct 10 – 12 2 nights · leave Sat$280$280 Book
American Airlines Nonstop · 2h 05m -
Oct 23 – 25 2 nights · leave Fri$287$287 Book
Porter Airlines Canada Nonstop · 1h 50m
-
Oct 7 – 14 7 nights · leave Wed$375 +32% vs usual$375 +32% vs usual Book
American Airlines Nonstop · 2h 10m
-
Nov 29 – Dec 1 2 nights · leave Sun$384 +35% vs usual$384 +35% vs usual Book
United Airlines Nonstop · 2h 09m -
Oct 9 – 11 2 nights · leave Fri$505 +78% vs usual$505 +78% vs usual Book
Porter Airlines Canada Nonstop · 1h 50m
Prices change often. The booking site shows the final price before you pay. Other dates? Set an alert
Things to do in Chicago
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Airport transfer to Chicago
Fixed prices from ORD on KiwitaxiTo see transfer prices here, turn on partner content in .
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Plan the rest of your trip
Chicago · Nov 18 – 27Travel insurance · EKTA Airport transfer · Kiwitaxi
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Good to know
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Toronto to Chicago: questions
How much is a flight from Toronto to Chicago?
The cheapest round trip we have found right now is $278, leaving November 18 and returning November 27. The usual price on this route is about $284, so this fare is 2% less. Prices are per person, economy, in USD.
What is the cheapest month to fly from Toronto to Chicago?
November 2026, with round trips from $278. The most expensive month in our data is March (from $380). Based on the 3 months ahead we have prices for.
About this route
We track round-trip economy fares from Toronto (Canada) to Chicago (United States) using Travelpayouts / Aviasales data. The cheapest round trip we've found is $278, departing November 18 and returning November 27 on a nonstop flight, about 2% below the usual $284. Right now we're following 6 upcoming date combinations on this route. The cheapest month to fly in our data is November, from $278. Prices are per person and were correct when found; the final price is set by the airline or booking site when you book.