Toronto to Chicago flights
The cheapest round trip we found from Toronto to Chicago is $252 (Dec 7 – 16, Nonstop), 13% below the usual $288.
YTO to CHI · Round trip · Economy · Prices per person in USD · Price found (2 days ago)
Cheapest found
Cheapest round trip by month
Lowest fare found per departure month| Month | Cheapest round trip |
|---|---|
| November 2026 | $273 |
| December 2026 | $252 (cheapest month) |
| January 2027 | No fares found yet |
| February 2027 | $303 |
| March 2027 | No fares found yet |
| April 2027 | No fares found yet |
| May 2027 | $407 |
Cheapest dates in the next 4 months
Round trip, per person-
Dec 7 – 16 9 nights · leave Mon$252 −13% vs usual$252 −13% vs usual Book
Porter Airlines Canada Nonstop · 2h 05m -
Dec 8 – 16 8 nights · leave Tue$252 −13% vs usual$252 −13% vs usual Book
Porter Airlines Canada Nonstop · 2h 05m
-
Feb 1 – 4, 2027 3 nights · leave Mon$303 +5% vs usual$303 +5% vs usual Book
Porter Airlines Canada Nonstop · 1h 55m
Prices change often. The booking site shows the final price before you pay. Other dates? Set an alert
Things to do in Chicago
One Go City pass for Shedd Aquarium, Skydeck Chicago, 360 CHICAGO and more
- All-Inclusive Pass Unlimited Visit as many attractions as you like for 1–5 days from $149 See pass
- Explorer Pass Pick 3–7 of 36 attractions from $109 See pass
- Essentials Pass A few top attractions, chosen as you go from $99 See pass
Go City prices checked Oct 23, 2026; the final price is on Go City. Partner links: we may earn a commission if you book, at no extra cost to you.
Plan the rest of your trip
Chicago · Dec 7 – 16- eSIM for United States Yesim · prepaid mobile data (opens Yesim in a new tab)
- Car rental Economybookings · compare rental companies (opens Economybookings in a new tab)
Partner links: we may earn a commission if you book, at no extra cost to you.
Good to know
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Toronto to Chicago: questions
How much does a flight from Toronto to Chicago cost?
The cheapest round trip we have found right now is $252, leaving December 7 and returning December 16. The usual price on this route is about $288, so this fare is 13% less. Prices are per person, economy, in USD.
What is the cheapest month to fly from Toronto to Chicago?
December 2026, with round trips from $252. The most expensive month in our data is May (from $407). Based on the 4 months ahead we have prices for.
Which airports do Toronto to Chicago flights use?
Toronto airports include Pearson International (YYZ), Hamilton (YHM) and Toronto City Centre (YTZ). Chicago airports include O'Hare International (ORD), Chicago Midway International (MDW) and Chicago Rockford International (RFD). The prices on this page cover every airport in both cities (YTO and CHI are the city codes).
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 $252, departing December 7 and returning December 16 on a nonstop flight, about 13% below the usual $288. The cheapest month to fly in our data is December, from $252. Prices are per person and were correct when found; the final price is set by the airline or booking site when you book.