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 $344, 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 $292. You can even find prices in April for less than $292, as users have found deals to Chicago Midway Airport from as low as $193. The month of September 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
$209 - $410
Route
Depart
Return
Price
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Fri 9/20
Nonstop1h 47m
Chicago Midway
Mon 9/23
Nonstop1h 42m
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Fri 5/31
Nonstop1h 47m
Chicago Midway
Tue 6/4
Nonstop1h 42m
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Fri 6/28
Nonstop1h 47m
Chicago Midway
Mon 7/1
Nonstop1h 42m
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Fri 6/14
Nonstop1h 47m
Chicago Midway
Mon 6/17
Nonstop1h 42m
CalgaryChicago Midway
YYC - MDW
YYCMDW
Calgary
Sat 10/26
1 stop10h 15m
Chicago Midway
Tue 10/29
1 stop9h 44m
CalgaryChicago Midway
YYC - MDW
YYCMDW
Calgary
Sat 10/26
1 stop10h 15m
Chicago Midway
Tue 10/29
1 stop9h 44m
Montreal Pierre Elliott Trudeau IntlChicago Midway
YUL - MDW
YULMDW
Montreal Pierre Elliott Trudeau Intl
Tue 5/21
2 stops24h 54m
Chicago Midway
Tue 5/28
1 stop4h 35m
Toronto Pearson IntlChicago Midway
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Tue 9/10
1 stop7h 34m
Chicago Midway
Tue 9/17
1 stop7h 11m
Toronto Pearson IntlChicago Midway
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Mon 5/27
1 stop7h 36m
Chicago Midway
Sun 6/2
1 stop6h 37m
No data available for this route at this time. Please check back soon.
Overall
Food
Boarding
Entertainment
Crew
Comfort
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.
Overall
Food
Boarding
Entertainment
Crew
Comfort
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.
Overall
Food
Boarding
Entertainment
Crew
Comfort
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.
Overall
Food
Boarding
Entertainment
Crew
Comfort
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.
Overall
Food
Boarding
Entertainment
Crew
Comfort
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.
1%of flight departures | Early morningMidnight to 6 am |
---|---|
29%of flight departures | Morning6 am to noon |
35%of flight departures | AfternoonNoon to 6 pm |
35%of flight departures | Evening6 pm to midnight |
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