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$ 359
February
C$ 418
March
C$ 446
April
C$ 458
May
C$ 537
June
C$ 585
July
C$ 601
August
C$ 604
September
C$ 473
October
C$ 513
November
C$ 465
December
C$ 480
Fly from
Budget
C$ 317 - C$ 527
Route
Depart
Return
Price
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Thu 23/5
Nonstop1h 47m
Chicago Midway
Sun 26/5
Nonstop1h 42m
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Thu 23/5
Nonstop1h 47m
Chicago Midway
Tue 28/5
Nonstop1h 42m
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Fri 24/5
Nonstop1h 47m
Chicago Midway
Sun 26/5
Nonstop1h 42m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 13/6
Nonstop1h 57m
Chicago O'Hare Intl
Sun 16/6
Nonstop1h 48m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 11/7
Nonstop1h 56m
Chicago O'Hare Intl
Tue 16/7
Nonstop1h 48m
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 24/5
Nonstop1h 56m
Chicago O'Hare Intl
Mon 27/5
Nonstop1h 45m
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
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 24/5
Nonstop1h 55m
Chicago O'Hare Intl
Fri 24/5
Nonstop1h 50m
Entertainment
Food
Overall
Comfort
Crew
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.
Entertainment
Food
Overall
Comfort
Crew
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.
Entertainment
Food
Overall
Comfort
Crew
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.
Entertainment
Food
Overall
Comfort
Crew
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.
Entertainment
Food
Overall
Comfort
Crew
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.
Entertainment
Food
Overall
Comfort
Crew
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 |
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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).