At the moment, the best time to book a non-stop flight to Chicago is in January with an average price of C$ 261. If you're looking to fly direct to Chicago in August, expect to pay the most, with an average price of C$ 439. Keep in mind that different factors like airlines, departure airports, and times can affect the cost of your flight, so it's a good idea to compare these to find the best deal.
January
C$ 358
February
C$ 417
March
C$ 444
April
C$ 457
May
C$ 535
June
C$ 583
July
C$ 600
August
C$ 602
September
C$ 472
October
C$ 512
November
C$ 464
December
C$ 479
Fly from
Budget
C$ 314 - C$ 506
Route
Depart
Return
Price
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Tue 28/5
Nonstop1h 47m
Chicago Midway
Tue 4/6
Nonstop1h 42m
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Fri 24/5
Nonstop1h 47m
Chicago Midway
Mon 27/5
Nonstop1h 42m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sun 16/6
Nonstop1h 56m
Chicago O'Hare Intl
Sat 22/6
Nonstop1h 43m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sat 29/6
Nonstop1h 56m
Chicago O'Hare Intl
Sun 7/7
Nonstop1h 48m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 31/5
Nonstop1h 54m
Chicago O'Hare Intl
Mon 3/6
Nonstop1h 45m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 23/5
Nonstop1h 54m
Chicago O'Hare Intl
Sun 26/5
Nonstop1h 45m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 31/5
Nonstop1h 56m
Chicago O'Hare Intl
Sat 1/6
Nonstop1h 35m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 23/5
Nonstop1h 55m
Chicago O'Hare Intl
Sun 26/5
Nonstop1h 40m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 24/5
Nonstop1h 56m
Chicago O'Hare Intl
Sun 26/5
Nonstop1h 40m
Food
Crew
Entertainment
Overall
Comfort
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.
Food
Crew
Entertainment
Overall
Comfort
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.
Food
Crew
Entertainment
Overall
Comfort
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.
Food
Crew
Entertainment
Overall
Comfort
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.
Food
Crew
Entertainment
Overall
Comfort
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.
Food
Crew
Entertainment
Overall
Comfort
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.
CHI Temperature | -5 - 23 °C |
---|
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).