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 80% on the cost of this flight compared to booking a flight leaving this week. We have found prices from C$ 714 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as C$ 1,044.
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$ 416 - C$ 649
Route
Depart
Return
Price
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Sat 31/8
1 stop8h 27m
Chicago O'Hare Intl
Fri 6/9
1 stop17h 43m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Wed 26/6
1 stop12h 47m
Chicago O'Hare Intl
Tue 2/7
2 stops20h 42m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Mon 22/7
1 stop12h 58m
Chicago O'Hare Intl
Tue 30/7
1 stop17h 23m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Mon 22/7
2 stops11h 49m
Chicago O'Hare Intl
Tue 30/7
1 stop17h 23m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Fri 14/6
1 stop8h 35m
Chicago O'Hare Intl
Sun 16/6
2 stops14h 02m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Sat 20/7
2 stops9h 37m
Chicago O'Hare Intl
Wed 24/7
2 stops16h 23m
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
Sun 16/6
2 stops9h 47m
Chicago Midway
Tue 18/6
2 stops10h 07m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Wed 26/6
Nonstop2h 28m
Chicago O'Hare Intl
Wed 3/7
Nonstop2h 26m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Wed 26/6
1 stop7h 41m
Chicago O'Hare Intl
Wed 3/7
Nonstop2h 26m
No data available for this route at this time. Please check back soon.
Boarding
Crew
Food
Comfort
Entertainment
Overall
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.
Boarding
Crew
Food
Comfort
Entertainment
Overall
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.
Boarding
Crew
Food
Comfort
Entertainment
Overall
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.
Boarding
Crew
Food
Comfort
Entertainment
Overall
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.
Boarding
Crew
Food
Comfort
Entertainment
Overall
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.
Boarding
Crew
Food
Comfort
Entertainment
Overall
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.
0%of flight departures | Early morningMidnight to 6 am |
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0%of flight departures | Morning6 am to noon |
100%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
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