- Cheapest round trip
- $577
- Dates
- Oct 4 to Oct 13 (9 nights)
- Flight
- Nonstop on American
- Flight time
- About 2 h 05 min each way
- Distance
- About 700 km from Toronto
We're still building this route's price history, so we can't yet say how $577 compares. When it drops well below its usual price, it shows up on our deals page.
Check these dates on Google Flights
Fares change constantly. This was the cheapest round trip of about a week that we found; other dates and trip lengths can cost more or less. Always confirm the price before you book, and book with the airline when you can.
What this route has cost recently
The cheapest round trip we found each day since July 30, 2026: as low as $291, typically about $323, and as high as $577. That's $254 more than a week ago.
Cheapest time to fly to Chicago
Based on one-way fares for every departure date over the coming months, compared with this route's typical fare:
| Month you leave | vs. typical | Lowest one-way |
|---|---|---|
| October 2026 | −17% | $198 |
| November 2026 | −27% | $198 |
| December 2026 | −11% | $198 |
| January 2027 | +2% | $278 |
| February 2027 | 0% | $278 |
| March 2027 | +1% | $278 |
November is the cheapest month to leave, and January the most expensive. The cheapest day of the week to fly out is usually Tuesday, and Friday the priciest. The cheapest single days to leave we've seen: Oct 4 ($198 one way), Oct 5 ($198 one way), Oct 6 ($198 one way), Oct 7 ($198 one way), Oct 8 ($198 one way).
Airlines and nonstop flights
There are nonstop flights from Toronto to Chicago. The airlines behind the cheapest fares we've found: Air Canada (from $323, nonstop), Air Canada and United (from $323, nonstop), American (from $519, nonstop).
More cheap flights from Toronto to the U.S.
OddFare checks the price of every destination from Toronto daily and flags the ones that drop well below normal. See today's deals or browse every route from Toronto.