To save on the cost of your flight from Winnipeg to Illinois, book at least 17 days before your planned departure. Booking around this time can save you about 115% on the cost of this flight compared to booking a flight leaving this week. We have found prices from C$ 745 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as C$ 1,043.
November is one of the best times of the year to fly to Illinois from Winnipeg. Prices for November average C$ 703 per person but you can even find prices for as low as C$ 372. The most expensive prices can be found in the month of August. Opting for a November flight can save you 16% on your journey compared to booking in August
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$ 406 - C$ 740
Route
Depart
Return
Price
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Wed 4/9
1 stop8h 01m
Chicago O'Hare Intl
Sat 7/9
2 stops9h 46m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Mon 27/5
1 stop8h 35m
Chicago O'Hare Intl
Sat 1/6
1 stop17h 47m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Tue 4/6
2 stops9h 38m
Chicago O'Hare Intl
Sat 8/6
1 stop7h 29m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Sat 25/5
2 stops9h 38m
Chicago O'Hare Intl
Wed 29/5
1 stop7h 33m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Sat 25/5
1 stop8h 35m
Chicago O'Hare Intl
Tue 28/5
1 stop18h 00m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Mon 27/5
1 stop8h 35m
Chicago O'Hare Intl
Sat 1/6
2 stops12h 48m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Thu 13/6
1 stop12h 47m
Chicago O'Hare Intl
Sun 16/6
2 stops13h 20m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Wed 12/6
Nonstop2h 28m
Chicago O'Hare Intl
Wed 19/6
1 stop11h 37m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Tue 3/9
Nonstop2h 32m
Chicago O'Hare Intl
Sat 7/9
Nonstop2h 26m
No data available for this route at this time. Please check back soon.
Crew
Comfort
Entertainment
Overall
Food
Boarding
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.
Crew
Comfort
Entertainment
Overall
Food
Boarding
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.
Crew
Comfort
Entertainment
Overall
Food
Boarding
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.
Crew
Comfort
Entertainment
Overall
Food
Boarding
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.
Crew
Comfort
Entertainment
Overall
Food
Boarding
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.
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