To save on the cost of your flight from Winnipeg to Illinois, book at least 24 days before your planned departure. Booking around this time can save you about 237% on the cost of this flight compared to booking a flight leaving this week. We have found prices from C$ 813 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as C$ 1,121.
April is one of the best times of the year to fly to Illinois from Winnipeg. Prices for April average C$ 728 per person but you can even find prices for as low as C$ 471. The most expensive prices can be found in the month of March. Opting for a April flight can save you 16% on your journey compared to booking in March
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Illinois as you normally would.
Fly from
Fly to
Budget
C$ 493 - C$ 657
Route
Depart
Return
Price
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
Sat 25/5
1 stop4h 07m
Chicago Midway
Wed 29/5
2 stops13h 51m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Mon 27/5
Nonstop2h 28m
Chicago O'Hare Intl
Sat 1/6
1 stop11h 40m
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
Tue 4/6
1 stop6h 40m
Chicago Midway
Sat 8/6
1 stop28h 44m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Tue 21/5
1 stop5h 04m
Chicago O'Hare Intl
Tue 28/5
2 stops13h 04m
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
Tue 21/5
1 stop5h 45m
Chicago Midway
Tue 28/5
2 stops11h 40m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Tue 21/5
3 stops27h 02m
Chicago O'Hare Intl
Tue 28/5
3 stops20h 11m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Sat 25/5
Nonstop2h 28m
Chicago O'Hare Intl
Wed 29/5
1 stop11h 40m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Tue 21/5
3 stops28h 02m
Chicago O'Hare Intl
Tue 28/5
3 stops20h 11m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Sat 25/5
Nonstop2h 28m
Chicago O'Hare Intl
Wed 29/5
Nonstop2h 26m
No data available for this route at this time. Please check back soon.
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
Terrible flight crew that skipped our row for service multiple times.
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