Open interactive map →Cheap flights from Toronto to Chicago
Planning a trip from Toronto to Chicago? Tracked fares start at €126 to United States. The cheapest tracked fare is non-stop. Use the price calendar to compare months SkyHopp has data for, then click through to check seats and dates.
SkyHopp's cheapest tracked fare from Toronto to Chicago is €126. The cheapest tracked fare is non-stop. The calendar above lists the months with data; more months are needed before naming a cheapest month.
Flying the other way? Cheap flights from Chicago to Toronto.
One-way fares
From €126
Cheapest tracked fare (non-stop)
Return fares
From €261
Tracked return fares (out 13 Nov 2026, back 15 Nov 2026)
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Get an email when Toronto to Chicago fares are at or below your target price. The email includes the fare.
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Cheapest month to fly
- November 2026€126DirectCheapest
SkyHopp has tracked fares for this route in November at around €126. That is the only month with data so far, so it is too early to name a cheapest month.
Cheapest fare last seen 22 October 2026.
Entry requirements for United States
EU passportESTA required (visa-waiver)
US passportN/A (domestic)
Requirements vary by nationality and change without notice. Check requirements for your nationality →
About Chicago
Chicago is the great American city that the coasts overlook - a dense, architecturally extraordinary lakefront city with world-class museums, deep-dish pizza, and jazz and blues venues that trace the music's northern migration. O'Hare (ORD) and Midway (MDW) together give the city one of the world's widest airport choices.
Alternative routes
Other ways to reach Chicago
Frequently asked questions
How much does a flight from Toronto to Chicago cost?
The cheapest tracked fare from Toronto to Chicago is €126. The month-by-month price calendar on this page lists the months SkyHopp has fares for. A tracked return fare on this pair is currently from €261. Fares are refreshed as our flight partners publish new availability.
Are there direct flights from Toronto to Chicago?
Yes - non-stop fares appear in SkyHopp's tracked data from Toronto to Chicago. The cheapest tracked fare, from €126, is itself non-stop. Click through to the booking site to check schedules for your dates.
When is the cheapest time to fly from Toronto to Chicago?
SkyHopp does not yet have enough months of fares on this route to name a cheapest month. The calendar above lists the months that already have data. Set a price alert on this page to watch the fare.