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	$177	Porter Airlines Nonstop 2 hr Thu, Jan 8 — Mon, Jan 12	The cheapest round-trip flight from Toronto to Chicago is currently $177
Cheapest one-way flight	$110	Porter Airlines Nonstop 2 hr Thu, Jan 8	The cheapest one-way flight from Toronto to Chicago is currently $110
Last-minute weekend getaway	$394	Air Canada, United 1 stop 7 hr Sat, Oct 18 — Sun, Oct 19	The cheapest last-minute weekend getaway from Toronto to Chicago is currently $394
Cheapest business class flights	$337	American Nonstop 3 hr Thu, Dec 4 — Sun, Dec 7	The cheapest business class round-trip flight from Toronto to Chicago is currently $337

Fastest flight	1 hr 49 min	The fastest nonstop flight from Toronto to Chicago takes 1 hr 49 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 August. The most expensive month to fly is typically November.

August Cheapest	Typical prices: $190–440
November Most expensive	Typical prices: $250–370

Popular airlines from Toronto to Chicago

United

Nonstop

from $183

Typical price: $230–400

47 weekly nonstop flights

YYZ - ORD Every day

75 weekly connecting flights

YYZ - ORD Every day
Air Canada

Nonstop

from $183

Typical price: $225–395

35 weekly nonstop flights

YYZ - ORD Every day

149 weekly connecting flights

YTZ, YYZ - ORD Every day
American

Nonstop

from $188

Typical price: $245–425

33 weekly nonstop flights

YYZ - ORD Every day

116 weekly connecting flights

YYZ - ORD Every day
Porter Airlines

Nonstop

from $177

Typical price: $215–385

13 weekly nonstop flights

YTZ - MDW Every day
Delta

from $210

Typical price: $255–580

213 weekly connecting flights

YYZ - MDW, ORD Every day
Alaska

from $463

Typical price: $550–1,300

21 weekly connecting flights

YYZ - ORD Every day

Popular airports near Toronto

Toronto Pearson International Airport (YYZ)

Toronto Canada 38 min 12 mi
Billy Bishop Toronto City Airport (YTZ)

Toronto Canada 35 min 2 mi
John C. Munro Hamilton International Airport (YHM)

Hamilton Canada 1 hr 6 min 43 mi
London International Airport (YXU)

London Canada 2 hr 2 min 98 mi

Popular airports near Chicago

Chicago O'Hare International Airport (ORD)

Chicago United States 39 min 16 mi
Chicago Midway International Airport (MDW)

Chicago United States 25 min 9 mi
Indianapolis International Airport (IND)

Indianapolis United States 2 hr 57 min 165 mi
Milwaukee Mitchell International Airport (MKE)

Milwaukee United States 1 hr 37 min 75 mi

Frequently asked questions about flying from Toronto to Chicago

When are the cheapest days to fly from Toronto to Chicago?

The cheapest flights from Toronto to Chicago are usually in August. Typical ticket prices in August range from $190 to $440.

Which airlines provide the cheapest flights from Toronto to Chicago?

The cheapest round-trip flight from Toronto to Chicago recently found on Google Flights was with Porter Airlines from $177. The cheapest one-way flight was with Porter Airlines from $110.

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

The cheapest United flight from Toronto to Chicago is $183, flying from Jan 8 to Jan 11.
The cheapest Air Canada flight from Toronto to Chicago is $183, flying from Jan 8 to Jan 11.
The cheapest American flight from Toronto to Chicago is $188, flying from Dec 4 to Dec 7.
The cheapest Porter Airlines flight from Toronto to Chicago is $177, flying from Jan 8 to Jan 12.
The cheapest Delta flight from Toronto to Chicago is $210, flying from Dec 4 to Dec 7.
The cheapest Alaska flight from Toronto to Chicago is $463, flying from Dec 6 to Dec 8.

What are the cheapest flights from Toronto to Chicago?

The cheapest round-trip flight from Toronto to Chicago starts at $177 from Thu, Jan 8 to Mon, Jan 12. The cheapest one-way flight starts at $110 and departs on Thu, Jan 8.

How long does it take to fly from Toronto to Chicago?

1 hr 49 min is the shortest flight time from Toronto to Chicago.

When should you fly to Chicago, United States?

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.

How do I find cheap dates to fly from Toronto to Chicago?

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 is the best airline to fly from Toronto to Chicago?

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 47 nonstop flights and 75 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 213 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:

Air Canada offers 35 nonstop flights and 149 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) .
American offers 33 nonstop flights and 116 connecting flights per week. American flies from 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 21 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.

Which airlines provide the cheapest flights from Toronto to Chicago?

The cheapest round-trip flight from Toronto to Chicago recently found on Google Flights was with Porter Airlines from $177. The cheapest one-way flight was with Porter Airlines from $110.

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

The cheapest United flight from Toronto to Chicago is $183, flying from Jan 8 to Jan 11.
The cheapest Air Canada flight from Toronto to Chicago is $183, flying from Jan 8 to Jan 11.
The cheapest American flight from Toronto to Chicago is $188, flying from Dec 4 to Dec 7.
The cheapest Porter Airlines flight from Toronto to Chicago is $177, flying from Jan 8 to Jan 12.
The cheapest Delta flight from Toronto to Chicago is $210, flying from Dec 4 to Dec 7.
The cheapest Alaska flight from Toronto to Chicago is $463, flying from Dec 6 to Dec 8.

Which airlines have direct flights from Toronto to Chicago?

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

There are 47 United direct flights from Toronto to Chicago per week. Flights are available every day.
There are 35 Air Canada direct flights from Toronto to Chicago per week. Flights are available every day.
There are 33 American 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.

Which airline provides the cheapest last-minute getaway flight from Toronto to Chicago?

The cheapest last-minute deal between Toronto and Chicago at price $394 is offered by Air Canada, United from Sat, Oct 18 to Sun, Oct 19.

Which airlines have direct flights from Toronto to Chicago?

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

There are 47 United direct flights from Toronto to Chicago per week. Flights are available every day.
There are 35 Air Canada direct flights from Toronto to Chicago per week. Flights are available every day.
There are 33 American 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.

When are direct flights from Toronto to Chicago available?

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

What are the cheapest direct flights from Toronto to Chicago?

The cheapest direct (nonstop) round-trip flights between Toronto and Chicago start at $177 from Thu, Jan 8 to Mon, Jan 12 with Porter Airlines.

How can I find nonstop flights from Toronto to Chicago?

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.

What are the cheapest business class flights from Toronto to Chicago?

The cheapest business class round-trip flights between Toronto and Chicago start at $337 from Thu, Dec 4 to Sun, Dec 7 with American.

What are the cheapest economy class flights from Toronto to Chicago?

The cheapest economy class round-trip flights between Toronto and Chicago start at $177 from Thu, Jan 8 to Mon, Jan 12.

How can I book business class trips from Toronto to Chicago?

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.

Are there any last-minute deals from Toronto to Chicago next weekend?

The best last-minute getaway deal for the next weekend between Toronto and Chicago starts at $394 from Sat, Oct 18 to Sun, Oct 19 with Air Canada, United.

Which airline provides the cheapest last-minute getaway flight from Toronto to Chicago?

The cheapest last-minute deal between Toronto and Chicago at price $394 is offered by Air Canada, United from Sat, Oct 18 to Sun, Oct 19.

How can I find last-minute flight deals from Toronto to Chicago?

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.