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$ 711 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as C$ 1,040.
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$ 371. 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$ 527 - C$ 655
Route
Depart
Return
Price
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Wed 12/6
1 stop12h 47m
Chicago O'Hare Intl
Mon 24/6
2 stops29h 34m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Wed 12/6
1 stop12h 47m
Chicago O'Hare Intl
Mon 24/6
3 stops25h 08m
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
Wed 12/6
1 stop6h 34m
Chicago Midway
Mon 24/6
1 stop13h 12m
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
Tue 23/7
2 stops10h 09m
Chicago Midway
Sat 27/7
1 stop4h 12m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Thu 4/7
2 stops17h 03m
Chicago O'Hare Intl
Sun 7/7
1 stop5h 31m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Sun 30/6
Nonstop2h 28m
Chicago O'Hare Intl
Sun 7/7
Nonstop2h 26m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Wed 28/8
1 stop20h 07m
Chicago O'Hare Intl
Mon 2/9
2 stops18h 27m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Sun 30/6
Nonstop2h 28m
Chicago O'Hare Intl
Sun 7/7
1 stop9h 57m
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
Sun 30/6
2 stops9h 47m
Chicago Midway
Sun 7/7
2 stops9h 12m
No data available for this route at this time. Please check back soon.
Crew
Overall
Boarding
Entertainment
Food
Comfort
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
Overall
Boarding
Entertainment
Food
Comfort
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
Overall
Boarding
Entertainment
Food
Comfort
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
Overall
Boarding
Entertainment
Food
Comfort
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
Overall
Boarding
Entertainment
Food
Comfort
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
Overall
Boarding
Entertainment
Food
Comfort
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 |
---|---|
0%of flight departures | Morning6 am to noon |
100%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
Cheapflights helps you search for flights from Winnipeg to Illinois via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.
Cheapflights helps you find that perfect flight to Illinois from Winnipeg by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!
Certainly. Search results for flights to Illinois from Winnipeg shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
Of course! You can now track prices for flights from Winnipeg to Illinois and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.