Find Cheap Flights from Toronto to Chicago (YTO - CHI)

Flights overview

Useful information for finding cheap flights from Toronto to Chicago and booking your next trip

Cheapest round-trip flights	$227	Porter Airlines Nonstop 2 hr Thu, May 28 — Sun, May 31	The cheapest round-trip flight from Toronto to Chicago is currently $227
Cheapest one-way flight	$136	Porter Airlines Nonstop 2 hr Wed, May 27	The cheapest one-way flight from Toronto to Chicago is currently $136
Last-minute weekend getaway	$390	American Nonstop 3 hr Sat, May 9 — Sun, May 10	The cheapest last-minute weekend getaway from Toronto to Chicago is currently $390
Cheapest business class flights	$440	American Nonstop 3 hr Fri, Jun 12 — Sun, Jun 14	The cheapest business class round-trip flight from Toronto to Chicago is currently $440

Fastest flight	1 hr 50 min	The fastest nonstop flight from Toronto to Chicago takes 1 hr 50 min
Nonstop flights	Every day	There are direct flights on this route every day.

When is the cheapest time to fly?

The cheapest month to fly from Toronto to Chicago is typically February. The most expensive month to fly is typically June.

February Cheapest	Typical prices: $190–420
June Most expensive	Typical prices: $205–345

Popular airlines from Toronto to Chicago

United

Nonstop

from $260

Typical price: $210–450

53 weekly nonstop flights

YYZ - ORD Every day

62 weekly connecting flights

YYZ - ORD Every day
American

Nonstop

from $237

Typical price: $225–460

35 weekly nonstop flights

YYZ - ORD Every day

90 weekly connecting flights

YYZ - ORD Every day
Air Canada

Nonstop

from $227

Typical price: $225–450

31 weekly nonstop flights

YYZ - ORD Every day

126 weekly connecting flights

YTZ, YYZ - ORD Every day
Porter Airlines

Nonstop

from $227

Typical price: $215–430

13 weekly nonstop flights

YTZ - MDW Every day
Delta

from $272

Typical price: $235–600

244 weekly connecting flights

YYZ - MDW, ORD Every day
Alaska

from $1,219

Typical price: $560–1,350

20 weekly connecting flights

YYZ - ORD Every day

Popular airports near Toronto

Toronto Pearson International Airport (YYZ)

Toronto Canada 33 min 12 mi
Billy Bishop Toronto City Airport (YTZ)

Toronto Canada 35 min 2 mi
Buffalo Niagara International Airport (BUF)

Buffalo United States 2 hr 59 mi
John C. Munro Hamilton International Airport (YHM)

Hamilton Canada 1 hr 1 min 43 mi

Popular airports near Chicago

Chicago O'Hare International Airport (ORD)

Chicago United States 26 min 16 mi
Chicago Midway International Airport (MDW)

Chicago United States 25 min 9 mi
Milwaukee Mitchell International Airport (MKE)

Milwaukee United States 1 hr 23 min 75 mi
Indianapolis International Airport (IND)

Indianapolis United States 2 hr 58 min 165 mi

Frequently asked questions about flying from Toronto to Chicago

The cheapest flights from Toronto to Chicago are usually in February. Typical ticket prices in February range from $190 to $420.

The cheapest round-trip flight from Toronto to Chicago recently found on Google Flights was with Porter Airlines from $227. The cheapest one-way flight was with Porter Airlines from $136.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest United flight from Toronto to Chicago is $260, flying from Jun 4 to Jun 7.
The cheapest American flight from Toronto to Chicago is $237, flying from May 21 to May 24.
The cheapest Air Canada flight from Toronto to Chicago is $227, flying from Jun 11 to Jun 14.
The cheapest Porter Airlines flight from Toronto to Chicago is $227, flying from May 28 to May 31.
The cheapest Delta flight from Toronto to Chicago is $272, flying from May 28 to Jun 1.
The cheapest Alaska flight from Toronto to Chicago is $1,219, flying from May 30 to May 31.

The cheapest round-trip flight from Toronto to Chicago starts at $227 from Thu, May 28 to Sun, May 31. The cheapest one-way flight starts at $136 and departs on Wed, May 27.

1 hr 50 min is the shortest flight time from Toronto to Chicago.

Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.

It's easy to use Google Flights to find the cheapest days to fly from Toronto to Chicago.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.

What counts as the best airline for your flights from Toronto to Chicago really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Toronto to Chicago.

In terms of nonstop flights, United is the most popular. United offers 53 nonstop flights and 62 connecting flights per week. United flies from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD) .

In terms of flights, Delta is the most popular. Delta offers 244 connecting flights per week. Delta flies from Toronto Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

Other popular airlines flying from Toronto to Chicago are:

American offers 35 nonstop flights and 90 connecting flights per week. American flies from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD) .
Air Canada offers 31 nonstop flights and 126 connecting flights per week. Air Canada flies from Billy Bishop Toronto City Airport (YTZ) , Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD) .
Porter Airlines offers 13 nonstop flights per week. Porter Airlines flies from Billy Bishop Toronto City Airport (YTZ) to Chicago Midway International Airport (MDW) .
Alaska offers 20 connecting flights per week. Alaska flies from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD) .

The number of connecting flights refers to distinct flights with at least one stop between Toronto and Chicago.

The cheapest round-trip flight from Toronto to Chicago recently found on Google Flights was with Porter Airlines from $227. The cheapest one-way flight was with Porter Airlines from $136.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest United flight from Toronto to Chicago is $260, flying from Jun 4 to Jun 7.
The cheapest American flight from Toronto to Chicago is $237, flying from May 21 to May 24.
The cheapest Air Canada flight from Toronto to Chicago is $227, flying from Jun 11 to Jun 14.
The cheapest Porter Airlines flight from Toronto to Chicago is $227, flying from May 28 to May 31.
The cheapest Delta flight from Toronto to Chicago is $272, flying from May 28 to Jun 1.
The cheapest Alaska flight from Toronto to Chicago is $1,219, flying from May 30 to May 31.

Porter Airlines, United, American and Air Canada fly direct from Toronto to Chicago.

There are 53 United direct flights from Toronto to Chicago per week. Flights are available every day.
There are 35 American direct flights from Toronto to Chicago per week. Flights are available every day.
There are 31 Air Canada direct flights from Toronto to Chicago per week. Flights are available every day.
There are 13 Porter Airlines direct flights from Toronto to Chicago per week. Flights are available every day.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

The cheapest last-minute deal between Toronto and Chicago at price $390 is offered by American from Sat, May 9 to Sun, May 10.

Porter Airlines, United, American and Air Canada fly direct from Toronto to Chicago.

There are 53 United direct flights from Toronto to Chicago per week. Flights are available every day.
There are 35 American direct flights from Toronto to Chicago per week. Flights are available every day.
There are 31 Air Canada direct flights from Toronto to Chicago per week. Flights are available every day.
There are 13 Porter Airlines direct flights from Toronto to Chicago per week. Flights are available every day.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

There are direct flights from Toronto to Chicago on a daily basis.

The cheapest direct (nonstop) round-trip flights between Toronto and Chicago start at $227 from Thu, May 28 to Sun, May 31 with Porter Airlines.

It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Toronto to Chicago, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.

The cheapest business class round-trip flights between Toronto and Chicago start at $440 from Fri, Jun 12 to Sun, Jun 14 with American.

The cheapest economy class round-trip flights between Toronto and Chicago start at $227 from Thu, May 28 to Sun, May 31.

To book business class trips from Toronto to Chicago, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.

The best last-minute getaway deal for the next weekend between Toronto and Chicago starts at $390 from Sat, May 9 to Sun, May 10 with American.

The cheapest last-minute deal between Toronto and Chicago at price $390 is offered by American from Sat, May 9 to Sun, May 10.

To find last-minute flight deals from Toronto to Chicago, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.