TorontoChicago

Flights from Toronto to Chicago

Nonstop flights from Toronto (YTZ) to Chicago (MDW) take about 1h 23m (713 km). Porter Airlines Canada and Porter Airlines fly it. Lowest fare seen: $142 one-way, nonstop (12 Oct 2026).

All flights from Toronto →All flights to Chicago →

Photo of Chicago: Mik Dominguez on Pexels.

When you land in Chicago

The airport transfer and the few things worth sorting before you fly.

A stunning view of Chicago's skyline and river with prominent skyscrapers and bridges on a cloudy day. — arriving in Chicago

Airport transfer

MDW → Chicago, booked before you fly

A private driver meets you in arrivals at a price agreed when you book. Book with Welcome Pickups.

See transfer prices

Before you flyAirport lounges at Billy Bishop Toronto City →1 lounge at Billy Bishop Toronto City Airport Trains, buses and taxi faresMDW to Chicago: getting into town →Early arrival or late flightLuggage storage in Chicago →11 drop-off points, from $4.90

Things to book in Chicago

All 59 things to do in Chicago →

Skyline view of Chicago's iconic skyscrapers including the John Hancock Center.

from €24.10

John Hancock Center 4.5 · 3,029 Tiqets reviews

The historic Tribune Tower in Chicago, featuring its gothic architecture and American flag.

from €26.78

Tribune Tower 4.6 · 2,764 Tiqets reviews

View of the historic Wrigley Building in downtown Chicago, showcasing its classic architecture.

from €13.38

The Wrigley Building 4.6 · 2,762 Tiqets reviews

Silhouette of visitors walking through a tunnel at Museum Campus, leading outdoors.

from €26.78

Museum Campus 4.6 · 2,641 Tiqets reviews

Find hotels in Chicago

Hotels, hostels & more · Trip.com

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Airlines flying Toronto to Chicago

Carriers on YTZ–MDW according to our route data and nonstop fares seen as of 12 Oct 2026. Not a complete list.

✈ Porter Airlines Canadanonstop fare seen✈ Porter Airlinesnonstop fare seen

Toronto to Chicago fares by month

Cheapest month seen for a nonstop flight: Nov 2026, from $135 one-way. Lowest one-way fares seen for departures in each month, read 22 Oct 2026.

Departing	Nonstop from	Cheaper with stops
Oct 2026	$20025 Oct 2026 · Porter Airlines Canada	—
Nov 2026	$13513 Nov 2026 · Porter Airlines Canada	—
Apr 2027	$14130 Apr 2027 · Porter Airlines Canada	$138 · 1 stop30 Apr 2027

When to go for the lowest fare

Fares were close across the months we saw: $135 for November 2026, $138 at best after that.

From Travelpayouts flight-search data, city to city (Toronto to Chicago, any airport), USD, read 22 Oct 2026. These are fares that were on sale, not a guarantee of today's price; an airline is named only where we know it flies this route.

More for this trip

Frequently asked questions — Toronto to Chicago flights

How long is the flight from Toronto to Chicago?

A nonstop flight from Toronto (YTZ) to Chicago (MDW) takes about 1h 23m, covering 713 km. That is an estimate from the distance — actual time varies with the airline, aircraft and winds, and connecting itineraries take longer.

How far is Toronto from Chicago by air?

The great-circle distance between Billy Bishop Toronto City Airport and Chicago Midway International Airport is 713 km (443 miles), a short-haul route.

Which airlines fly from Toronto to Chicago?

Airlines with flights or nonstop fares on the YTZ–MDW route include Porter Airlines Canada and Porter Airlines. This is not a complete list — schedules change by season, so check the current options before booking.

How much does a flight from Toronto to Chicago cost?

The lowest one-way fare seen recently on YTZ–MDW was $142 USD with Porter Airlines Canada (nonstop), departing 14 Oct 2026, found in fare searches as of 12 Oct 2026. Fares change constantly and depend on the date, so check the current price before booking.

What is the cheapest month to fly from Toronto to Chicago?

In fares seen on 22 Oct 2026, departures in November 2026 were cheapest, from $135 one-way, against $200 for October 2026, the dearest month. Fares change daily, so check your own dates.

Do I need a visa to travel from Toronto to Chicago?

It depends on your passport. Some nationalities can enter Chicago visa-free or get a visa on arrival; others must apply in advance. Use AirConnect's Visa Checker to see the rules for your passport.

Sources: fares from Travelpayouts flight-search data, seen 12 Oct 2026; airlines from each carrier's published network and nonstop fares on sale; distance from OurAirports coordinates; flight time estimated from distance. Fares change daily.

Ready to book YTZ–MDW?

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