Fareseeker
Home › YYZ › ORD

Cheap flights from Toronto (YYZ) to Chicago (ORD)

YYZ Toronto
ORD Chicago
15
Flights
$449
Lowest
$539
Average
Oct 10, 2026 - Mar 5, 2027
Date Range
49% above typical Check live prices Alert me on this route

Round-trip Toronto to Chicago currently starts at $449 CAD with taxes included, averaging $539 across 15 tracked fares departing Oct 10, 2026 to Mar 5, 2027.

YYZ to ORD price history

Cheapest right now $449
Typical low $301
58-day range $274 to $534

49% above the typical low ($301), so this is a poor time to buy.

Sep 6, 2026 Typical low $301 Oct 6, 2026

Prices on this route swing 49% between their best and worst day. Get an alert when it drops

↑ Trending up: 28.7% above the last 30-day average.

· FareSeeker tracking data: 15 fares monitored on this route by our own collector, refreshed several times daily.

The 5 cheapest fares right now

Dates Trip Airline Stops Price
Nov 19, 2026 → Nov 29, 2026 10 nights AC Air Canada Nonstop $449 CAD
Nov 19, 2026 → Nov 28, 2026 9 nights AC Air Canada Nonstop $449 CAD
Nov 4, 2026 → Nov 12, 2026 8 nights AC Air Canada Nonstop $449 CAD
Nov 4, 2026 → Nov 14, 2026 10 nights AC Air Canada Nonstop $449 CAD
Nov 24, 2026 → Dec 3, 2026 9 nights AC Air Canada Nonstop $508 CAD

All fares are round trip. Exact flight times show on the booking page.

Good to know:

No flights match your filters

Try adjusting your filters to see more results

Popular routes we track

Vancouver to Victoria from $129 Winnipeg to Reykjavik from $1,053 Montreal to Santiago de Querétaro from $582 Quebec City to Lisbon from $758 Montreal to Tokyo from $1,164 Montreal to Liberia from $421 Vancouver to Yellowknife from $390 Vancouver to Paris from $652 Halifax to Paris from $867 Ottawa to Cancún from $493 Montreal to Lisbon from $634 Prince George to Terrace from $466 Toronto to Podgorica from $1,375 San Juan to Toronto from $460 Ottawa to Lisbon from $797 Montreal to Chicago from $521 Montreal to Cozumel from $616 Vancouver to Los Angeles from $242 Toronto to Halifax from $199 Toronto to Fort Lauderdale from $247 Toronto to St. John's from $301 Atlanta to Calgary from $508 Halifax to Ottawa from $482 Montreal to Fort McMurray from $840 Vancouver to Phoenix from $224 Calgary to Halifax from $369 Quebec City to Puerto Vallarta from $584 Halifax to Glasgow from $1,258 Montreal to Monterrey from $702 Montreal to Boston from $393 Montreal to Halifax from $359 Ottawa to Toronto from $323 Montreal to Vancouver from $310 Toronto to Saskatoon from $253 Regina to Toronto from $294 Victoria to Vancouver from $129 Ottawa to Calgary from $290 Vancouver to Comox from $189 Vancouver to Kelowna from $150 Kelowna to Edmonton from $153 Montreal to Toronto from $290 Victoria to Kelowna from $199 Saskatoon to Toronto from $247 Montreal to Nassau from $538 Halifax to Nassau from $531 Winnipeg to Toronto from $199 Kelowna to Vancouver from $150 Toronto to Austin from $317
Get these deals in your feed Follow us on Facebook
Follow on Facebook