Chicago → Toronto flights

Chicago–Toronto fares hover near $167 — modest upside if you shop around

Key takeaways

• Median fare sits at $167, with observed prices ranging from $122 to $188
• Bottom quartile (25th percentile) comes in at $139 — a realistic target if you have flexibility
• Top quartile matches the median at $167, suggesting fares cluster tightly above the low end
• Spread of 54% between low and high shows real variability worth monitoring
• Sample size is thin — only 12 snapshots — so treat these figures as directional, not definitive

30-day price trend

See full numbers and stats on the ORD → YYZ price history page.

The full picture

The data shows a median round-trip fare of $167 between Chicago and Toronto, with a range stretching from $122 at the low end to $188 at the high end — a 54% spread. That's a meaningful gap for a short-haul route, suggesting fares aren't static and there's room to land well below median if your timing lines up. The 25th percentile of $139 is a useful anchor: it tells us a meaningful share of fares do dip into that lower band, so it's not an outlier fluke.

With only 12 snapshots in this dataset, we can't make confident claims about a precise booking window or day-of-week pattern — the sample is too thin to separate signal from noise. What we can say is that the 75th percentile equals the median ($167), meaning the upper half of observed fares is fairly compressed. Most of the real variability in this route comes from the lower half of the distribution, between $122 and $167. That points to occasional discounting rather than a predictable climb as travel dates approach, though we don't have enough data to say when in the booking horizon those dips tend to occur.

No dominant carrier was identifiable from this data, so we can't speak to airline-specific pricing behavior on this route. The honest takeaway: budget around $167 as a typical fare, treat anything near $139 or below as a good deal worth booking quickly, and don't expect a strong pattern tied to specific days — the sample size here simply isn't large enough to support that kind of precision. Revisiting this analysis with a larger data window would sharpen these estimates considerably.

Ready to look at fares?

• When to book
  Chicago → Toronto
  AI-authored booking-window guide
  Open →
• Price history
  Chicago → Toronto
  30-day daily price snapshots
  Open →
• Where to stay
  Best hotels in Toronto
  🇨🇦 Canada
  Open →
• When to book
  Chicago → London
  Same origin, different destination
  Open →
• Read
  Wildlife in Banff National Park: What to Look For
  Canada · 6 min
  Open →