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$ 284 - C$ 353
CHI
Temperature
1 - 29 °C
CHI
Precipitation
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$ 284

From Toronto to Chicago

One-way from

C$ 171

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?

Tuesday is generally a great day to depart. Flying on this day could help you save up to 8%.

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$ 439.

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

April is one of the best times of the year to fly to Chicago from Toronto. Prices for April average C$ 320 per person but you can even find prices for as low as C$ 242. The most expensive prices can be found in the month of January. Opting for a April flight can save you 10% on your journey compared to booking in April

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 September, October 2021

The best prices found for YTO to CHI flights for September, October
30 Oct - 7 Nov
C$ 286pp
YYZ
Toronto Pearson Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
YYZ
Toronto Pearson Intl
12 Oct - 19 Oct
C$ 295pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
30 Oct - 7 Nov
C$ 296pp
YYZ
Toronto Pearson Intl
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
YYZ
Toronto Pearson Intl

Toronto to Chicago 2021 flight deals

Cheap flights to Chicago from Toronto found for this year
4 Nov - 7 Nov
C$ 257pp
YYZ
Toronto Pearson Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
YYZ
Toronto Pearson Intl
4 Nov - 8 Nov
C$ 258pp
YYZ
Toronto Pearson Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
YYZ
Toronto Pearson Intl
4 Nov - 7 Nov
C$ 273pp
YYZ
Toronto Pearson Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
YYZ
Toronto Pearson Intl

Direct flights to Chicago from Toronto

Save time with Toronto to Chicago direct flight deals
15 Dec - 29 Dec
C$ 294pp
YTZ
Toronto Island
Major Airline
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Major Airline
Direct
YTZ
Toronto Island
1 Nov - 27 Nov
C$ 295pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
7 Oct - 11 Oct
C$ 299pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

Last minute flights from Toronto to Chicago

Late deals on round-trip flights to Chicago from Toronto, departing today and this week
23 Sep - 25 Dec
C$ 406pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
22 Sep - 3 Oct
C$ 413pp
YTZ
Toronto Island
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YTZ
Toronto Island
22 Sep - 3 Oct
C$ 413pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

One-way flights to Chicago from Toronto

The cheapest one-way flights from Toronto to Chicago
1:10 a.m. - 2:04 a.m.
Air Canada
Direct
1h 54m
YYZ - ORD
Air Canada
C$ 171
mytrip.com
3:00 a.m. - 4:31 p.m.
Multiple Airlines
1 stop
14h 31m
YYZ - ORD
Multiple Airlines
C$ 181
Gotogate
8:55 a.m. - 9:48 a.m.
Porter Airlines
Direct
1h 53m
YTZ - MDW
Porter Airlines
C$ 182
Travelgenio

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

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.

Can I find flights from Toronto to Chicago for under C$ 300 on Cheapflights?

Yes, there are multiple flights from Toronto to Chicago for under C$ 300. The cheapest flight booked recently is on Multiple Airlines for just C$ 257, but on average you can expect to pay C$ 289.

Are there direct flights from Toronto to Chicago for under C$ 300 on Cheapflights?

Cheapflights has 20 direct flights from Toronto to Chicago under C$ 300. A good price for a direct flight from Toronto to Chicago is less than C$ 311.

Are there last-minute flights available from Toronto to Chicago for under C$ 500?

There are currently 20+ open flights from Toronto to Chicago within the next 7 days for less than C$ 500.

What days are direct flights available from Toronto to Chicago?

You can find direct flights on the following days: Friday.

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

1 flight departure from Toronto to Chicago per day on average.
Morning (6am - Midday) - 100% of flight departures

How long is the flight from Toronto to Chicago?

Air Canada, Porter Airlines, and ANA can get you from Toronto to Chicago in just under 1h 50m. Your travel time can differ by up to 3h 27m. Toronto and Chicago are separated by a distance of 703 km. This flight may include one or multiple stops.

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

Flying on Air Canada is currently your cheapest option to Chicago, with prices starting at C$ 292. Additional round-trip tickets that might be worth considering are offered by Porter Airlines and ANA, with the lowest prices starting at C$ 295 and C$ 308, respectively. Users have found that Air Canada is 8% cheaper than the other options available to this destination.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from Toronto?

Information is based on travel restrictions from Toronto to Chicago

Most visitors from Toronto need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Toronto must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from Toronto are not required to quarantine after entering Chicago.

Do I need a test to fly back to Toronto from Chicago?

Returning to Toronto from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) test taken 72 hours before departing to Toronto.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Toronto.

Hide COVID Travel Restrictions for Chicago, IL

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 = $0.79
Flight duration from Toronto to Chicago
1h 47m
Average temperature for September in Chicago
25.0 °C
Avg rainfall for September in Chicago
60.0 mm

Airports servicing Toronto

Toronto Island (YTZ)
Hamilton (YHM)
Kitchener-Waterloo (YKF)

Airports servicing 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.
Afternoon Noon to 6 PM 63% of YTO to US-CHI departures
Morning 6 AM to noon 26% of YTO to US-CHI departures
Early morning Midnight to 6 AM 11% 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
21 daily flights
Monday
24 daily flights
Tuesday
23 daily flights
Wednesday
24 daily flights
Thursday
21 daily flights
Friday
22 daily flights
Saturday
17 daily flights
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