Popular in | July |
---|---|
Cheapest in | January |
Round-trip from | C$ 358 |
One-way from | C$ 206 |
Friday is generally a great day to depart. Flying on this day could help you save up to 9%.
Find a great deal and save up to 78% by booking at least 27 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$ 490.
January is one of the best times of the year to fly to Chicago from Toronto. Prices for January average C$ 398 per person but you can even find prices for as low as C$ 243. The most expensive prices can be found in the month of July. Opting for a January flight can save you 16% on your journey compared to booking in July
Unlike in the afternoon, when flights are generally more expensive, you can save up to 6% on flights from Toronto to Chicago by exploring options for tickets in the evening.
Fly from
Fly to
Budget
C$ 279 - C$ 434
Route
Depart
Return
Price
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 14/5
1 stop12h 10m
Chicago O'Hare Intl
Wed 15/5
3 stops31h 37m
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Thu 23/5
Nonstop1h 47m
Chicago Midway
Thu 30/5
Nonstop1h 42m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 24/5
Nonstop1h 54m
Chicago O'Hare Intl
Fri 31/5
Nonstop1h 48m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sat 8/6
1 stop5h 18m
Chicago O'Hare Intl
Sat 22/6
1 stop4h 05m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sun 26/5
1 stop4h 31m
Chicago O'Hare Intl
Sun 2/6
Nonstop1h 48m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 2/8
Nonstop1h 55m
Chicago O'Hare Intl
Wed 7/8
1 stop5h 43m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 23/5
Nonstop1h 56m
Chicago O'Hare Intl
Sun 26/5
Nonstop1h 40m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Mon 27/5
2 stops11h 39m
Chicago O'Hare Intl
Fri 31/5
1 stop5h 00m
Toronto Pearson IntlChicago Midway
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Sun 4/8
1 stop7h 40m
Chicago Midway
Fri 9/8
1 stop6h 35m
Currently, January is the cheapest month in which you can book a flight from Toronto to Chicago (average of C$ 261). Flying from Toronto to Chicago in August is currently the most expensive (average of C$ 452). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
January
C$ 357
February
C$ 415
March
C$ 443
April
C$ 455
May
C$ 535
June
C$ 560
July
C$ 605
August
C$ 617
September
C$ 473
October
C$ 508
November
C$ 462
December
C$ 477
CHI Temperature | -5 - 23 °C |
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Entertainment
Food
Overall
Boarding
Crew
Comfort
Reviews
Terrible flight crew that skipped our row for service multiple times.
Entertainment
Food
Overall
Boarding
Crew
Comfort
Reviews
Terrible flight crew that skipped our row for service multiple times.
Entertainment
Food
Overall
Boarding
Crew
Comfort
Reviews
Terrible flight crew that skipped our row for service multiple times.
Entertainment
Food
Overall
Boarding
Crew
Comfort
Reviews
Terrible flight crew that skipped our row for service multiple times.
Entertainment
Food
Overall
Boarding
Crew
Comfort
Reviews
Terrible flight crew that skipped our row for service multiple times.
Entertainment
Food
Overall
Boarding
Crew
Comfort
Reviews
Terrible flight crew that skipped our row for service multiple times.
O’Hare International Airport is on the northwest side of the city in Chicago. It’s about 14 miles away from the city centre. The airport was built to take over for Midway originally. It’s a busy airport that is a hub for major airlines like United and American Airlines.
Midway International Airport used to be the main airport in Chicago until O’Hare came along. This airport is still the second busiest one in the state of Illinois though. This is a major hub for Southwest Airlines.
9%of flight departures | Early morningMidnight to 6 am |
---|---|
35%of flight departures | Morning6 am to noon |
50%of flight departures | AfternoonNoon to 6 pm |
6%of flight departures | Evening6 pm to midnight |
Sunday | 54daily flights |
---|---|
Monday | 57daily flights |
Tuesday | 51daily flights |
Wednesday | 48daily flights |
Thursday | 57daily flights |
Friday | 66daily flights |
Saturday | 46daily flights |
Deals for Toronto to Chicago flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Toronto.
Cheapflights does show flights with no change fees to all users. To see these options for flights from Toronto to Chicago, users can toggle the no change fees filter when performing a flight search.
Yes, Cheapflights offers price alerts on Toronto to Chicago flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.