Fly from
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 to Chicago (average of C$ 261). Flying to Chicago in August will prove the most costly (average of C$ 440). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.
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
Peak Season:
Summer runs from June through August and is a hugely popular time in the city, despite the heat and humidity from the Lake. This is also the Chicago’s peak festival season, which sees major events taking place in the parks and neighbourhoods every weekend. Prices for flights to Chicago and crowd numbers can see an increase when the city hosts its most popular festivals.
Foodies should book a flight to Chicago during mid-July for the Taste of Chicago festival. This outdoor food event takes place at the lakefront and showcases a variety of cuisines and local flavours accompanied by live music. August is host to another popular event – the Chicago Air and Water Show. With free admission and lakefront location, the show attracts huge numbers of fans of aviation and adventure seekers.
September can be the most enjoyable and mild month of the year but there’s less going on during this period.
Off-peak Season:
January to March is when Chicago is least busy, making cheap flights to Chicago and hotel deals more attainable. However, true to its reputation as the “Windy City”, cold temperatures and brisk winds will make you want to stay inside for most of your visit.
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).
Crew
Food
Comfort
Entertainment
Boarding
Overall
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
Food
Comfort
Entertainment
Boarding
Overall
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
Food
Comfort
Entertainment
Boarding
Overall
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
Food
Comfort
Entertainment
Boarding
Overall
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
Food
Comfort
Entertainment
Boarding
Overall
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
Food
Comfort
Entertainment
Boarding
Overall
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.