Flights to Chicago
The cheapest flights to Chicago from every Canadian airport we track. Prices are updated every few hours.
We track flights to Chicago from 3 Canadian airports and update the prices every few hours.
The cheapest round trip fare we found right now is CAD$388 from Toronto, for a trip leaving around November 27.
1 deal is live. The biggest saving is Toronto: CAD$404, 22% below its usual price.
The cheapest months to leave right now: November (CAD$388), December (CAD$404) and February (CAD$401).
Fares change quickly. Get free alerts and we email you when a fare to Chicago drops well below its usual price.
Fares well below their usual price. Checked automatically before they are shown.
Save 111 · 22% below usual
Tue, Dec 8 to Wed, Dec 16
USAReviewed Fri, Nov 13in 24 daysNonstopAir Canada8-day trip
Found in recent searches · checked 5 h 34 min ago. The live price may differ. Prices in CAD; Aviasales may show USD.
The lowest round trip price we found for each route, for trips leaving 7 days to 3 months from now.
Fri, Nov 27 to Sun, Nov 29
USAin 13 daysNonstop2-day trip
Found in recent searches · checked 5 h 34 min ago. The live price may differ. Prices in CAD; Aviasales may show USD.
The lowest round trip fare we found for each departure month.
| Month | Lowest fare |
|---|---|
| November 2026 | CAD$388 |
| December 2026 | CAD$404 |
| February 2027 | CAD$401 |
The lowest round trip fare we found is CAD$388 from Toronto, leaving around November 27. Prices come from recent searches and change quickly, so check the live price before you book.
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