
Keep the following information in mind while searching for Canada to Midway flight deals. Data was last updated November 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $304 (Delta) |
One-way from | $180 (Delta) |
Popular in | October |
Cheapest in | February |
Average price | $288 |
Good round-trip deal | $214 or less |
Good one-way deal | $247 or less |
Fly from
Fly to
Route
Depart
Return
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Sat 1/9
6:10 am-9:16 am
1 stop4h 06m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Thu 12/17
12:15 pm-6:01 pm
1 stop6h 46m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Mon 1/11
6:10 am-1:17 pm
1 stop8h 07m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Tue 12/1
6:00 am-9:37 am
1 stop4h 37m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Tue 1/19
12:10 pm-6:00 pm
1 stop6h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Sun 1/17
6:10 am-9:16 am
1 stop4h 06m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Sun 1/10
6:10 am-9:16 am
1 stop4h 06m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
MontrealChicago
YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway
YULMDW
Montreal Pierre Elliott Trudeau Intl
Wed 12/16
6:00 am-9:37 am
1 stop4h 37m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
MontrealChicago
YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway
YULMDW
Montreal Pierre Elliott Trudeau Intl
Sun 11/15
6:00 am-12:51 pm
1 stop7h 51m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Tue 12/15
6:00 am-9:37 am
1 stop4h 37m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
Everything you need to know about your flight from Canada to Chicago Midway Airport
Entertainment
Boarding
Crew
Overall
Comfort
Food
Reviews
D,Sep 2026
YHM - YVR
Entertainment
Boarding
Crew
Overall
Comfort
Food
Reviews
D,Sep 2026
YHM - YVR
Find useful and relevant information for your journey from Canada to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$185 | Average$365 | FlexibilityNo cancel fee | On-time52% |