Cheap flights from Toronto to Chicago

Round-trip
Economy
Toronto (YTO)
Chicago (CHI)
Depart
Return
Any month
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The best prices from Toronto to Chicago are usually found in April or March, booked 46 days in advance, depart on a Wednesday or Thursday and return on a Sunday

How to find the cheapest flight from
Toronto (YTO) to Chicago (CHI)

All the information you need to plan the best YTO to CHI flight in 2021: compare Toronto to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
YTO - CHI
Price
C$ 275 - C$ 343
CHI
Temperature
1 - 29 °C
CHI
Rainfall
17 - 109 mm

Popular in

January

High demand for flights, 9% potential price rise

Cheapest in

April

Best time to find cheap flights, 11% potential price drop

Round-trip from

C$ 275

From Toronto to Chicago

One-way from

C$ 227

One-way flight from Toronto to Chicago

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Toronto to Chicago?

Travellers have found that booking a Tuesday departure is the best way to save up to 8% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

How far in advance should I book a flight from Toronto to Chicago?

Find a great deal and save up to 86% by booking at least 34 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Toronto to Chicago within the next two weeks, with the cheapest ticket starting at C$ 426.

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

Flights from Toronto to Chicago lean towards being more expensive in January. Prices are generally better when you fly from Toronto to Chicago in April, with the cheapest ticket starting at C$ 235.

When is the cheapest time to fly from Toronto to Chicago (YTO - CHI)?

Unlike in the evening, when flights are generally more expensive, you can save up to 9% on flights from Toronto to Chicago by exploring options for tickets at noon.

Cheap flights from Toronto to Chicago in May, June 2021

The best prices found for YTO to CHI flights for May, June
2 Jun - 3 Jun
C$ 341pp
YYZ
Toronto Pearson Intl
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Direct
YYZ
Toronto Pearson Intl
17 Jun - 20 Jun
C$ 343pp
YYZ
Toronto Pearson Intl
Air Canada
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YYZ
Toronto Pearson Intl
17 Jun - 20 Jun
C$ 346pp
YYZ
Toronto Pearson Intl
Air Canada
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl

Toronto to Chicago 2021 flight deals

Cheap flights to Chicago from Toronto found for this year
2 Jun - 3 Jun
C$ 341pp
YYZ
Toronto Pearson Intl
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Direct
YYZ
Toronto Pearson Intl
17 Jun - 20 Jun
C$ 343pp
YYZ
Toronto Pearson Intl
Air Canada
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YYZ
Toronto Pearson Intl
17 Jun - 20 Jun
C$ 346pp
YYZ
Toronto Pearson Intl
Air Canada
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl

Direct flights to Chicago from Toronto

Save time with Toronto to Chicago direct flight deals
31 Aug - 22 Sep
C$ 351pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
17 Jun - 20 Jun
C$ 355pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
20 May - 29 May
C$ 356pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl

Last minute flights from Toronto to Chicago

Late deals on round-trip flights to Chicago from Toronto, departing today and this week
12 May - 18 May
C$ 444pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
12 May - 18 May
C$ 449pp
YYZ
Toronto Pearson Intl
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
YYZ
Toronto Pearson Intl
14 May - 16 May
C$ 469pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl

One-way flights to Chicago from Toronto

The cheapest one-way flights from Toronto to Chicago
6:55 a.m. - 7:42 a.m.
Porter Airlines
Direct
1h 47m
YTZ - MDW
Porter Airlines
C$ 228
4:10 a.m. - 10:58 a.m.
Air Canada
2 stops
7h 48m
YYZ - ORD
Air Canada
C$ 231
2:10 a.m. - 4:50 a.m.
Delta
1 stop
3h 40m
YYZ - MDW
Delta
C$ 235
Delta

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Toronto</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From Toronto to Chicago

Can I find flights from Toronto to Chicago for under C$ 368 on Cheapflights?

Yes, there are multiple flights from Toronto to Chicago for under C$ 368. The cheapest flight booked recently is on American Airlines for just C$ 341, but on average you can expect to pay C$ 361.

What safety measures are being taken by airlines flying from Toronto to Chicago to control the spread of COVID-19?

Airlines globally have implemented additional safety measures to accommodate you. Delta is one of them. Airline carriers are regularly disinfecting and sanitizing their aircraft. Masks are provided and are mandatory while on board. Pre-flight testing for symptoms and antibodies, alongside socially-distanced seating (for a limited time) will work towards keeping travellers safer while flying from Toronto to Chicago. Policies will vary by airline.

Which airlines flying from Toronto to Chicago have flexible cancellations due to COVID-19?

Air Canada, American Airlines, and United Airlines are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Are there direct flights from Toronto to Chicago for under C$ 368 on Cheapflights?

Cheapflights has 20 direct flights from Toronto to Chicago under C$ 368. A good price for a direct flight from Toronto to Chicago is less than C$ 382.

Are there last-minute flights available from Toronto to Chicago for under C$ 491?

There are currently 16+ open flights from Toronto to Chicago within the next 7 days for less than C$ 491.

What days are direct flights available from Toronto to Chicago?

Days when direct flights are available for this flight are: Sunday, Monday, Friday, Saturday.

How many flights depart from Toronto to Chicago on average per day?

Per day, 4 flights depart from Toronto to Chicago on average.
Morning (6am - Noon) - 50% of flight departures
Afternoon (Noon - 6pm) - 50% of flight departures

Is Toronto weather warmer or cooler than Chicago?

With an average temperature of 29 °C, peak weather can be found in July. As a traveller, expect to see changes in flight prices during that period. The temperatures in Chicago are hotter than in Toronto.

How long is the flight from Toronto to Chicago?

Departing from Toronto to Chicago will take you 1h 47m. The distance between Toronto and Chicago is about 703 km. Most flights are nonstop.

What are the cheapest airlines to flying from Toronto to Chicago round-trip?

American Airlines, at C$ 342, was found to be the cheapest airline from Toronto to Chicago.Alternate airlines to your destination round-trip include Air Canada and Porter Airlines.

What are the cheapest airlines to fly from Toronto to Chicago one-way?

The cheapest airline one-way is Air Canada, with whom users have recently found tickets for as low as C$ 191. However, be on the lookout for offers from Porter Airlines and Delta, as they are both options that can get you from Toronto to Chicago for a low price.

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Toronto to Chicago.
Today's exchange rate
C$ 1 = $0.82
Flight duration
1h 45m
Average temperature for May in Chicago
22.0 °C
Avg rainfall for May in Chicago
109.0 mm

Airports servicing Toronto

Billy Bishop Toronto City Airport (YTZ)
Hamilton (YHM)
Kitchener (YKF)

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 6 airlines flying from Toronto to Chicago

The chart below displays the airlines Cheapflights users travelling from Toronto to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Porter Airlines
C$ 171 C$ 286 No cancel fee 52%
Search Porter Airlines flights
Air Canada
C$ 140 C$ 299 No cancel fee 67%
Search Air Canada flights
United Airlines
C$ 176 C$ 312 No cancel fee 69%
Search United Airlines flights
American Airlines
C$ 130 C$ 346 No cancel fee 71%
Search American Airlines flights
WestJet
C$ 177 C$ 370 No cancel fee 60%
Search WestJet flights
Delta
C$ 206 C$ 385 No cancel fee N/A
Search Delta flights

Hourly flight availability from Toronto to Chicago

See what time of day planes typically take off from Toronto towards Chicago.
Morning 6 AM to noon 75% of YTO to US-CHI departures
Afternoon Noon to 6 PM 24% of YTO to US-CHI departures
Early morning Midnight to 6 AM 1% of YTO to US-CHI departures
Evening 6 PM to midnight 0% of YTO to US-CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Toronto to Chicago
See how many times per day planes take to the skies headed from Toronto to Chicago.
Sunday
7 daily flights
Monday
15 daily flights
Tuesday
11 daily flights
Wednesday
13 daily flights
Thursday
6 daily flights
Friday
8 daily flights
Saturday
4 daily flights
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