Cheap flights from Toronto to Chicago

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The best prices from Toronto to Chicago are usually found in February or March, booked 60 days in advance, depart on a Wednesday or Thursday and return on a Monday

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

YTO - CHI
Price
C$ 219 - C$ 273
CHI
Temperature
1 - 29 °C
CHI
Rainfall
17 - 109 mm
Popular in August High demand for flights, 9% potential price rise
Cheapest in February Best time to find cheap flights, 12% potential price drop
Round-trip from C$ 219 From Toronto to Chicago
One-way from C$ 116 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 81% by booking at least 57 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$ 609.

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

Flights from Toronto to Chicago lean towards being more expensive in August. Prices are generally better when you fly from Toronto to Chicago in February, with the cheapest ticket starting at C$ 248.

Cheap flights from Toronto to Chicago in July, August 2020

The best prices found for YTO to CHI flights for July, August
23 Jun - 30 Jun
C$ 196pp
YYZ
Toronto Pearson Intl
Qantas Airways
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Qantas Airways
Direct
YYZ
Toronto Pearson Intl
18 Jun - 21 Jun
C$ 197pp
YYZ
Toronto Pearson Intl
Qantas Airways
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Qantas Airways
Direct
YYZ
Toronto Pearson Intl
9 Jul - 12 Jul
C$ 198pp
YYZ
Toronto Pearson Intl
British Airways
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
British Airways
 
1 STOP
YYZ
Toronto Pearson Intl

Toronto to Chicago 2020 flight deals

Cheap flights to Chicago from Toronto found for this year
25 Sep - 27 Sep
C$ 188pp
YYZ
Toronto Pearson Intl
Japan Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Japan Airlines
Direct
YYZ
Toronto Pearson Intl
20 Oct - 4 Nov
C$ 192pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
25 Sep - 27 Sep
C$ 193pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

Direct flights to Chicago from Toronto

Save time with Toronto to Chicago direct flight deals
25 Sep - 27 Sep
C$ 188pp
YYZ
Toronto Pearson Intl
Japan Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Japan Airlines
Direct
YYZ
Toronto Pearson Intl
20 Oct - 4 Nov
C$ 192pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
25 Sep - 27 Sep
C$ 193pp
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 Jun - 30 Jun
C$ 196pp
YYZ
Toronto Pearson Intl
Qantas Airways
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Qantas Airways
Direct
YYZ
Toronto Pearson Intl
23 Jun - 30 Jun
C$ 199pp
YYZ
Toronto Pearson Intl
British Airways
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
British Airways
 
1 STOP
YYZ
Toronto Pearson Intl
28 Jun - 5 Jul
C$ 200pp
YYZ
Toronto Pearson Intl
British Airways
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
British Airways
 
1 STOP
YYZ
Toronto Pearson Intl

One-way flights to Chicago from Toronto

The cheapest one-way flights from Toronto to Chicago
1:35 p.m. - 2:34 p.m.
Lufthansa
Direct
1h 59m
YYZ - ORD
Lufthansa
C$ 158
4:59 a.m. - 5:46 a.m.
Porter Airlines
Direct
1h 47m
YTZ - MDW
Porter Airlines
C$ 167
4:15 a.m. - 5:14 a.m.
Royal Jordanian
Direct
1h 59m
YYZ - ORD
Royal Jordanian
C$ 170
Ovago

Related info for your journey

Useful info, stats and facts about Toronto to Chicago flights.

Flight FAQs

From Toronto to Chicago

Can I find flights from Toronto to Chicago for under C$ 200 on Cheapflights?

Yes, there are multiple flights from Toronto to Chicago for under C$ 200. The cheapest flight booked recently is on Japan Airlines for just C$ 188, but on average you can expect to pay C$ 197.

Are there direct flights from Toronto to Chicago for under C$ 200 on Cheapflights?

Cheapflights has 20 direct flights from Toronto to Chicago under C$ 200. A good price for a direct flight from Toronto to Chicago is less than C$ 199.

Are there last-minute flights available from Toronto to Chicago for under C$ 200?

There are currently 20+ open flights from Toronto to Chicago within the next 7 days for less than C$ 200.

What days are direct flights available from Toronto to Chicago?

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

How popular is this flight route?

Flights from Toronto to Chicago have been viewed 1,432 times in the past calendar month.

What is the cheapest airline for this route?

American Eagle, Inc. offers the cheapest flights from Toronto to Chicago. Per day you can find on average 174 flights for this route and airline.

How long does the flight from Toronto to Chicago take?

Your journey will take you approximately 2 hours. Your flight will cover a distance of about 437 kilometres.

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) - 100% 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.

Destination information for Chicago

Things to know before you go. Useful info for your trip from Toronto to Chicago
Today's exchange rate
C$ 1 = $0.74
Flight duration
1h 45m
Average temperature for July in Chicago
29.0 °C
Avg rainfall for July in Chicago
95.0 mm

Airports servicing Toronto

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

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Hourly flight availability from Toronto to Chicago

Morning 6 AM to noon 43% of YTO to US-CHI departures
Afternoon Noon to 6 PM 32% of YTO to US-CHI departures
Early morning Midnight to 6 AM 25% 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
Sunday
19 daily flights
Monday
21 daily flights
Tuesday
16 daily flights
Wednesday
12 daily flights
Thursday
18 daily flights
Friday
19 daily flights
Saturday
12 daily flights