Lowest fares from Toronto to Chicago
Toronto to Chicago at a glance
- Nonstop flights
- Air Canada, American Airlines and United
- Flying time
- About 1h 20m nonstop
- Distance
- 701 km
- Leaving from
- Toronto Pearson (YYZ), plus Billy Bishop (YTZ) downtown for short flights
- Arriving at
- O'Hare (ORD) and Midway (MDW)
- Time difference
- Chicago is about 1 hour behind Toronto (this can shift by an hour when clocks change).
- Cheapest time
- January to March is usually cheapest; summer is peak season.
- Entry for Canadians
- Canadian citizens don't need a visa for tourist trips to the US, but a valid passport is required to fly. Rules change, so confirm on the Government of Canada's travel advice page before you book.
Nonstop airlines are based on each airport's published routes (September 2026). Schedules change, so always check your dates.
Cheapest month to fly Toronto to Chicago
Lowest one-way fare in Canadian dollars (CAD) found in recent searches for each month. Round trips usually cost a bit less than two one-way tickets. Tap a month to search it.
Toronto to Chicago fares in our daily checks
We check the cheapest one-way fare from Toronto to Chicago every morning. We have 27 days of results so far, from Oct 15, 2026 to Nov 10, 2026. In Canadian dollars:
- Lowest fare we saw
- $185 one way, on Oct 23, 2026 (for travel in November 2026)
- Typical daily low
- $188 to $232: the middle half of each day's cheapest fare
- Latest check
- $232 on Nov 10, 2026
- Cheapest travel month so far
- April 2027 (median $194 over 7 days); priciest: December 2026 (median $332)
- Airlines selling these fares
- Porter Airlines Canada, Air Canada, American Airlines, United Airlines
- Stops on the cheapest fare
- Usually nonstop (20 of 27 days)
From Viorvo's own daily price checks (Travelpayouts fare data). These are the lowest one-way fares found in searches that day, not a quote, and they can be gone by the time you search. How we work these out.
How these figures are worked out, and what they are not: our data and method.
How to fly Toronto to Chicago for less
- Compare nonstop with one-stop. Nonstop on this route: Air Canada, American Airlines and United. One-stop fares are sometimes cheaper, but check how much time they add before you choose.
- Be flexible by a few days. Use the month chart and the Viorvo price calendar to see which days are cheapest; midweek departures are often lower.
- Compare airports on both ends. Buffalo (BUF), across the border, is sometimes much cheaper for US trips, and Hamilton (YHM), about an hour away, has budget flights too.
- Getting to the airport in Toronto: The UP Express train runs from Pearson to Union Station in about 25 minutes, usually far cheaper than a taxi.
- Arriving in Chicago: The CTA Blue Line (from O'Hare) and Orange Line (from Midway) reach downtown for a transit fare.
- Check what's included. The cheapest fares often exclude checked bags and seat selection, so compare the total price for your trip.
Free tools: Will my bag fit? Carry-on size checker · Flight delayed? See what you're owed
Power in United States: Type A, B, 120 V; Canadian plugs fit. Which adapter to pack · Flight packing list
Everything else for Chicago
Our guides: Chicago travel hub · Travel insurance for the US
Get the cheapest fares from Toronto, weekly
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The seven steps we use to tell a good fare from a bad one, plus a before-you-pay checklist. Chapter 1 of our Cheap Flights from Canada Playbook.
Toronto to Chicago flights: common questions
How much is a flight from Toronto to Chicago?
In recent searches, round trips from Toronto to Chicago started at $376 and one-way fares started at $232. Fares change daily, so check the fares board above for the latest prices and dates.
Is there a direct flight from Toronto to Chicago?
Yes. Nonstop flights between Toronto and Chicago: Air Canada, American Airlines and United. Schedules change, so the fares board above shows what's available for your dates.
How long is the flight from Toronto to Chicago?
A nonstop flight covers about 701 km and takes roughly 1h 20m. With one connection, the whole trip usually takes about 3 to 5 hours depending on the layover.
Which airlines fly from Toronto to Chicago?
Nonstop: Air Canada, American Airlines and United. Many other airlines sell connecting trips, and the fares board above compares them all, cheapest first.
When is the cheapest time to fly from Toronto to Chicago?
January to March is usually cheapest; summer is peak season. The month chart above shows the cheapest months in recent searches.
Which airports serve Chicago?
Chicago is served by O'Hare (ORD) and Midway (MDW). Comparing every airport is one of the easiest ways to find a cheaper fare.
What do Canadians need to travel to Chicago?
Canadian citizens don't need a visa for tourist trips to the US, but a valid passport is required to fly. Rules change, so confirm on the Government of Canada's travel advice page before you book.
What's the time difference between Toronto and Chicago?
Chicago is about 1 hour behind Toronto (this can shift by an hour when clocks change).
How much have Toronto to Chicago fares varied in your price checks?
In 27 days of daily checks (from Oct 15, 2026 to Nov 10, 2026), the cheapest one-way fare on a typical day was between $188 and $232 and the lowest we saw was $185. April 2027 has been the cheapest travel month so far.
What's the cheapest month to fly from Toronto to Chicago?
See the month chart above for the cheapest month in recent searches. As a rule of thumb: January to March is usually cheapest; summer is peak season.