Toronto → Chicago
Flights from Toronto to Chicago
Toronto
Chicago
Nonstop flights link Toronto and Chicago.
- Nonstop fare seen
- from £138 one way
- Straight-line distance
- 703 km
Searched and booked on Aviasales. Head Your Way may earn a commission at no extra cost to you.
What this is based on
Arrive inChicago →- The fare was found on 14 Sep 2026 and is a past price, not a quote.
- Source: Fare search by Travelpayouts, 14 Sep 2026. How Head Your Way works.
Continue from Chicago
Direct connections from Chicago
A few of the 937 direct connections we hold, larger places first. Not a popularity ranking.
New York🚆 Traindirect · from 20 h 12 min · 10 departures a weekView this connection →Los Angeles🚆 Traindirect · from 44 h 04 min · 10 departures a weekView this connection →Milwaukee🚆 Traindirect · from 1 h 14 min · 110 departures a weekView this connection →San Antonio🚆 Traindirect · from 32 h 36 min · 10 departures a weekView this connection →Dallas🚆 Traindirect · from 21 h 58 min · 10 departures a weekView this connection →Aurora🚆 Traindirect · from 52 min · 327 departures a weekView this connection →Fort Worth🚆 Traindirect · from 23 h 35 min · 10 departures a weekView this connection →Madison🚌 Coachdirect · from 3 h 50 min · 105 departures a weekView this connection →Janesville🚌 Coachdirect · from 3 h · 105 departures a weekView this connection →Madrid✈ Flight, Spainnonstop · fare seen from £480View this connection →Toronto✈ Flight, Canadanonstop · fare seen from £142View this connection →Montréal✈ Flight, Canadanonstop · fare seen from £242View this connection →
Any place we know, by any mix of train, coach, ferry, flight and road. Looking at results does not change your route.
Every direct connection from Chicago
Airports: Chicago Meigs Airport (CGX); Chicago Midway International Airport (MDW); Chicago O'Hare International Airport (ORD), 26 km away; Waukegan National Airport (UGN), 66 km away · Stations: Chicago Union Station; Chicago OTC; LaSalle Street; Millennium Station and 4 more · Ports: Chicago
Journeys through Chicago
Itineraries for ideas. They open in a new tab and do not change your route.
Other ways from Toronto to Chicago
Other ways to leave Toronto