Cheap flights from Chicago to Toronto
The cheapest round trip from Chicago to Toronto that travelers found recently is $292 with a carry-on: a $292 fare on Porter, which usually includes a carry-on. It leaves Wed, Nov 11 and comes back Sat, Nov 21.
Live prices for Wed, Nov 11 to Sat, Nov 21
Cheapest trips travelers found recently
| Leave | Return | Airline | Airports | Stops | Fare | Carry-on (est.) | Total | Live prices |
|---|---|---|---|---|---|---|---|---|
| Wed, Nov 11 | Sat, Nov 21 | Porter | ORD → YTZ | Nonstop | $292 | Included | $292 | Live price |
| Sat, Oct 31 | Tue, Nov 10 | Porter | ORD → YTZ | Nonstop | $295 | Included | $295 | Live price |
| Thu, Nov 12 | Mon, Nov 16 | Porter | ORD → YTZ | Nonstop | $295 | Included | $295 | Live price |
| Tue, Nov 10 | Sun, Nov 22 | Porter | ORD → YTZ | Nonstop | $296 | Included | $296 | Live price |
| Wed, Nov 11 | Mon, Nov 23 | Porter | ORD → YTZ | Nonstop | $296 | Included | $296 | Live price |
| Mon, Dec 7 | Mon, Dec 14 | Porter | ORD → YTZ | Nonstop | $296 | Included | $296 | Live price |
| Thu, Nov 12 | Sun, Nov 22 | Porter | ORD → YTZ | Nonstop | $300 | Included | $300 | Live price |
| Thu, Oct 29 | Sun, Nov 8 | Porter | ORD → YTZ | Nonstop | $302 | Included | $302 | Live price |
| Thu, Oct 15 | Fri, Oct 16 | United | ORD → YYZ | Nonstop | $328 | Included | $328 | Live price |
| Wed, Nov 18 | Thu, Nov 19 | P3 | ORD → YTZ | Nonstop | $330 | Included | $330 | Live price |
Round-trip prices per person, from real fares travelers found in the last few days. Carry-on fees are our estimate for each airline, both ways. Prices change fast: check the live price before you book.
Cheapest month to fly
| Month | Cheapest trip | From | Live prices |
|---|---|---|---|
| October 2026 | Sat, Oct 31 to Tue, Nov 10, 10 nights | $295 | Live price |
| November 2026 | Wed, Nov 11 to Sat, Nov 21, 10 nights | $292 | Live price |
| December 2026 | Mon, Dec 7 to Mon, Dec 14, 7 nights | $296 | Live price |
Bag fees on this route
What the airlines flying Chicago to Toronto usually charge for one bag each way. Budget airlines often sell the cheapest fares and charge the most for bags, so compare the total, not the fare.
| Airline | Carry-on, each way | Checked bag, each way |
|---|---|---|
| Air Canada | Included | $40 |
| Frontier | $55 | $50 |
| P3 | Included | $40 |
| Porter | Included | $40 |
| United | Included | $40 |
Our estimates: fees depend on the fare type and when you pay. Check the airline's own price when you book.
How these prices work
These are real round-trip fares that travelers found on Aviasales recently, not a live search, so they can change or sell out. Dipt adds an estimate of each airline's carry-on fee, so a cheap fare with expensive bags doesn't look cheaper than it is. "Live price" opens Dipt's live flight search for those dates, where you book with the airline or travel site you pick. Dipt may earn a commission when you book, at no extra cost to you (how Dipt makes money).
Not sure where to go? Tell Dipt your budget and vibe and it finds the trip.
More cheap flights from Chicago
- Chicago to Amsterdam
- Chicago to Athens
- Chicago to Atlanta
- Chicago to Austin
- Chicago to Bali
- Chicago to Bangkok
- Chicago to Barcelona
- Chicago to Berlin
- Chicago to Boston
- Chicago to Cancún
- Chicago to Cartagena
- Chicago to Denver
- Chicago to Dublin
- Chicago to Honolulu
- Chicago to Las Vegas
- Chicago to Lisbon
- Chicago to London
- Chicago to Los Angeles
- Chicago to Medellín
- Chicago to Mexico City
- Chicago to Miami
- Chicago to Montréal
- Chicago to Nashville
- Chicago to New Orleans
- Chicago to New York
- Chicago to Paris
- Chicago to Reykjavík
- Chicago to San Diego
- Chicago to San Francisco
- Chicago to San Juan
- Chicago to Seattle
- Chicago to Seoul
- Chicago to Tokyo