Travelers have found it’s best to book a flight 17 days in advance to save up to 80% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 17 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Winnipeg to Illinois 1-2 weeks in advance for as low as $522, or $763 for flights within the next 24 hours.
Due to multiple factors, expect to potentially pay more when booking in August. For low rates, November can be a great choice for travel to Illinois. Flights to Illinois from Winnipeg in November are about $514 on average during November, but can be found for as low as $272.
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
$304 - $474
Route
Depart
Return
Price
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Sat 8/31
1 stop8h 27m
Chicago O'Hare Intl
Fri 9/6
1 stop17h 43m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Wed 6/26
1 stop12h 47m
Chicago O'Hare Intl
Tue 7/2
2 stops20h 42m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Mon 7/22
1 stop12h 58m
Chicago O'Hare Intl
Tue 7/30
1 stop17h 23m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Mon 7/22
2 stops11h 49m
Chicago O'Hare Intl
Tue 7/30
1 stop17h 23m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Fri 6/14
1 stop8h 35m
Chicago O'Hare Intl
Sun 6/16
2 stops14h 02m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Sat 7/20
2 stops9h 37m
Chicago O'Hare Intl
Wed 7/24
2 stops16h 23m
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
Sun 6/16
2 stops9h 47m
Chicago Midway
Tue 6/18
2 stops10h 07m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Wed 6/26
Nonstop2h 28m
Chicago O'Hare Intl
Wed 7/3
Nonstop2h 26m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Wed 6/26
1 stop7h 41m
Chicago O'Hare Intl
Wed 7/3
Nonstop2h 26m
No data available for this route at this time. Please check back soon.
Comfort
Boarding
Crew
Overall
Food
Entertainment
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.
Comfort
Boarding
Crew
Overall
Food
Entertainment
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.
Comfort
Boarding
Crew
Overall
Food
Entertainment
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.
Comfort
Boarding
Crew
Overall
Food
Entertainment
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.
Comfort
Boarding
Crew
Overall
Food
Entertainment
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.
Comfort
Boarding
Crew
Overall
Food
Entertainment
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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