Travelers have found it’s best to book a flight 38 days in advance to save up to 90% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 38 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Canada to Chicago Midway Airport 1-2 weeks in advance for as low as $337, or $489 for flights within the next 24 hours.
The best pricing can be found in the month of April. Prices to Chicago Midway Airport from Canada average $290. You can even find prices in April for less than $290, as users have found deals to Chicago Midway Airport from as low as $193. The month of August appears to be one of the more expensive times to travel to Chicago Midway Airport from Canada. Flying in the targeted month can save you up to 14%.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Canada to Chicago Midway Airport as you normally would.
Fly from
Fly to
Budget
$210 - $387
Route
Depart
Return
Price
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Mon 7/1
Nonstop1h 47m
Chicago Midway
Fri 7/5
Nonstop1h 42m
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Wed 7/3
Nonstop1h 47m
Chicago Midway
Sat 7/6
Nonstop1h 42m
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Thu 8/1
Nonstop1h 47m
Chicago Midway
Sun 8/11
Nonstop1h 42m
Vancouver IntlChicago Midway
YVR - MDW
YVRMDW
Vancouver Intl
Tue 9/10
1 stop9h 24m
Chicago Midway
Wed 9/11
1 stop12h 58m
Vancouver IntlChicago Midway
YVR - MDW
YVRMDW
Vancouver Intl
Mon 9/9
2 stops12h 25m
Chicago Midway
Wed 9/11
1 stop12h 58m
Vancouver IntlChicago Midway
YVR - MDW
YVRMDW
Vancouver Intl
Tue 9/10
2 stops11h 40m
Chicago Midway
Sun 9/15
1 stop13h 04m
Toronto Pearson IntlChicago Midway
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Wed 7/3
1 stop5h 35m
Chicago Midway
Sat 7/6
1 stop6h 39m
Toronto Pearson IntlChicago Midway
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Sat 7/6
1 stop16h 31m
Chicago Midway
Wed 7/10
1 stop9h 53m
OttawaChicago Midway
YOW - MDW
YOWMDW
Ottawa
Tue 9/10
1 stop5h 27m
Chicago Midway
Fri 9/13
1 stop3h 39m
No data available for this route at this time. Please check back soon.
Food
Crew
Boarding
Comfort
Entertainment
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.
Food
Crew
Boarding
Comfort
Entertainment
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.
Food
Crew
Boarding
Comfort
Entertainment
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.
Food
Crew
Boarding
Comfort
Entertainment
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.
Food
Crew
Boarding
Comfort
Entertainment
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.
Food
Crew
Boarding
Comfort
Entertainment
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.
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Porter Airlines | Cheapest$206 | Average$362 | FlexibilityNo cancel fee | On-time52% |
1%of flight departures | Early morningMidnight to 6 am |
---|---|
31%of flight departures | Morning6 am to noon |
37%of flight departures | AfternoonNoon to 6 pm |
31%of flight departures | Evening6 pm to midnight |