Round-trip from | $212 (Kiwi.com) |
---|---|
One-way from | $149 (Trip.com) |
Popular in | April |
Cheapest in | June |
Average price | $449 |
Good round-trip deal | $385 or less |
Good one-way deal | $361 or less |
Fly from
Fly to
Route
Depart
Return
Price
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Wed 9/24
8:30 am-4:43 pm
1 stop8h 13m
Chicago O'Hare Intl
Sat 9/27
1:40 pm-9:25 pm
1 stop7h 45m
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Sat 9/13
7:00 pm-9:51 am
2 stops14h 51m
Chicago O'Hare Intl
Sat 9/20
1:40 pm-9:25 pm
1 stop7h 45m
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Fri 9/12
12:00 pm-8:11 pm
1 stop8h 11m
Chicago O'Hare Intl
Fri 9/19
10:40 am-6:59 pm
1 stop8h 19m
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Thu 9/18
2:20 pm-4:51 pm
Nonstop2h 31m
Chicago O'Hare Intl
Sun 9/21
1:01 pm-3:31 pm
Nonstop2h 30m
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Sat 9/13
6:40 am-12:28 pm
2 stops5h 48m
Chicago Midway
Sat 9/20
1:08 pm-11:27 pm
2 stops10h 19m
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Fri 9/19
6:30 am-8:40 am
2 stops26h 10m
Chicago Midway
Tue 9/23
7:15 pm-8:11 pm
1 stop24h 56m
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Wed 8/27
6:55 pm-8:45 am
1 stop13h 50m
Chicago Midway
Wed 9/3
5:20 pm-9:41 am
1 stop16h 21m
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Tue 9/9
5:30 pm-4:43 pm
1 stop23h 13m
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Tue 9/2
8:55 pm-4:43 pm
1 stop19h 48m
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Sat 9/20
2:20 pm-4:51 pm
Nonstop2h 31m
The price you pay for your flight from Winnipeg to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 67 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Currently, August is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of $245). Flying from Winnipeg to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
A simple way to save on the total cost of your ticket is to fly from Winnipeg to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 30% on your trip compared to booking a flight at noon.
The most flights from YWG to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).
Entertainment
Comfort
Boarding
Crew
Overall
Food
Reviews
Anonymous,Jul 2025
LIS - YYZ
Entertainment
Comfort
Boarding
Crew
Overall
Food
Reviews
Anonymous,Jul 2025
LIS - YYZ
Entertainment
Comfort
Boarding
Crew
Overall
Food
Reviews
Anonymous,Jul 2025
LIS - YYZ
Entertainment
Comfort
Boarding
Crew
Overall
Food
Reviews
Anonymous,Jul 2025
LIS - YYZ
Entertainment
Comfort
Boarding
Crew
Overall
Food
Reviews
Anonymous,Jul 2025
LIS - YYZ
Entertainment
Comfort
Boarding
Crew
Overall
Food
Reviews
Anonymous,Jul 2025
LIS - YYZ
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$199 | Average$546 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$230 | Average$645 | FlexibilityNo cancel fee | On-time67% |