Popular in | September |
---|---|
Cheapest in | April |
Round-trip from | C$ 351 |
One-way from | C$ 207 |
Friday is generally a great day to depart. Flying on this day could help you save up to 10%.
Find a great deal and save up to 90% by booking at least 38 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$ 469.
April is one of the best times of the year to fly to Chicago from Toronto. Prices for April average C$ 398 per person but you can even find prices for as low as C$ 263. The most expensive prices can be found in the month of September. Opting for a April flight can save you 14% on your journey compared to booking in September
Unlike in the afternoon, when flights are generally more expensive, you can save up to 5% on flights from Toronto to Chicago by exploring options for tickets in the evening.
If you’re travelling from Toronto to Chicago, one of the more common airlines travelling that route is Air Canada. Flights from Air Canada travelling this route typically cost C$ 321.64 RT. This price is typically 102% cheaper than other airlines that offer Toronto to Chicago flights. When booking this route, the cheapest RT price found was C$ 237. When travelling from Toronto to Chicago on Air Canada, the most popular airport to depart from is Toronto Pearson Intl Airport and the most popular airport to arrive at is Chicago O'Hare Intl Airport. When flying from Toronto to Chicago, Air Canada flights are 6% more popular than any other airline flying that same route.
If you’re travelling from Toronto to Chicago, one of the more common airlines travelling that route is American Airlines. Flights from American Airlines travelling this route typically cost C$ 240.73 RT. This price is typically 138% cheaper than other airlines that offer Toronto to Chicago flights. When booking this route, the cheapest RT price found was C$ 219. Toronto Pearson Intl Airport is the most common Toronto airport to take off from when flying to Chicago. Chicago O'Hare Intl Airport is the most popular arrival airport in Chicago. When flying from Toronto to Chicago, American Airlines flights are 4% more popular than any other airline flying that same route.
Fly from
Fly to
Budget
C$ 296 - C$ 416
Route
Depart
Return
Price
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Tue 18/6
Nonstop1h 47m
Chicago Midway
Mon 24/6
Nonstop1h 42m
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Thu 13/6
Nonstop1h 47m
Chicago Midway
Sat 15/6
Nonstop1h 42m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 4/6
1 stop12h 10m
Chicago O'Hare Intl
Tue 11/6
1 stop18h 20m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 10/7
Nonstop1h 54m
Chicago O'Hare Intl
Wed 17/7
Nonstop1h 48m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 7/6
Nonstop1h 55m
Chicago O'Hare Intl
Sun 9/6
Nonstop1h 50m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sun 16/6
Nonstop1h 57m
Chicago O'Hare Intl
Tue 18/6
1 stop9h 13m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 16/7
1 stop6h 54m
Chicago O'Hare Intl
Thu 18/7
1 stop7h 08m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 18/6
1 stop4h 17m
Chicago O'Hare Intl
Fri 5/7
1 stop4h 33m
Toronto Pearson IntlChicago Midway
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Mon 17/6
1 stop8h 19m
Chicago Midway
Wed 19/6
1 stop6h 34m
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$ 440). 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$ 356
February
C$ 414
March
C$ 441
April
C$ 454
May
C$ 477
June
C$ 550
July
C$ 591
August
C$ 599
September
C$ 466
October
C$ 508
November
C$ 460
December
C$ 475
CHI Temperature | -5 - 23 °C |
---|
Crew
Overall
Comfort
Food
Entertainment
Boarding
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Crew
Overall
Comfort
Food
Entertainment
Boarding
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Crew
Overall
Comfort
Food
Entertainment
Boarding
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Crew
Overall
Comfort
Food
Entertainment
Boarding
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Crew
Overall
Comfort
Food
Entertainment
Boarding
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Crew
Overall
Comfort
Food
Entertainment
Boarding
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
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.
11%of flight departures | Early morningMidnight to 6 am |
---|---|
26%of flight departures | Morning6 am to noon |
50%of flight departures | AfternoonNoon to 6 pm |
13%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.
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