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$ 742 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as C$ 1,038.
November is one of the best times of the year to fly to Illinois from Winnipeg. Prices for November average C$ 700 per person but you can even find prices for as low as C$ 370. 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$ 384 - C$ 898
Route
Depart
Return
Price
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Tue 4/6
2 stops9h 38m
Chicago O'Hare Intl
Sat 8/6
2 stops10h 04m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Fri 14/6
1 stop22h 52m
Chicago O'Hare Intl
Sun 16/6
1 stop29h 19m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Tue 18/6
1 stop8h 27m
Chicago O'Hare Intl
Tue 25/6
1 stop10h 54m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Tue 18/6
1 stop8h 27m
Chicago O'Hare Intl
Tue 25/6
2 stops16h 37m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Tue 18/6
2 stops15h 27m
Chicago O'Hare Intl
Tue 25/6
2 stops13h 22m
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
Fri 14/6
1 stop6h 34m
Chicago Midway
Sun 16/6
1 stop8h 26m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Tue 18/6
Nonstop2h 28m
Chicago O'Hare Intl
Tue 25/6
1 stop11h 37m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Thu 13/6
Nonstop2h 28m
Chicago O'Hare Intl
Sun 16/6
1 stop8h 07m
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
Thu 18/7
2 stops9h 32m
Chicago Midway
Tue 23/7
2 stops9h 52m
No data available for this route at this time. Please check back soon.
Entertainment
Crew
Comfort
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.
Entertainment
Crew
Comfort
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.
Entertainment
Crew
Comfort
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.
Entertainment
Crew
Comfort
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.
Entertainment
Crew
Comfort
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.
Entertainment
Crew
Comfort
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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