Travelers have found it’s best to book a flight 17 days in advance to save up to 115% 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 $545, 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
$295 - $562
Route
Depart
Return
Price
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Fr 6/14
1 stop22h 52m
Chicago O'Hare Intl
So 6/16
1 stop29h 19m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Di 6/4
1 stop10h 19m
Chicago O'Hare Intl
Sa 6/8
1 stop7h 29m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Sa 6/15
1 stop8h 27m
Chicago O'Hare Intl
Mi 6/19
2 stops14h 02m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Sa 6/15
1 stop8h 10m
Chicago O'Hare Intl
Mi 6/19
1 stop17h 24m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Fr 6/14
3 stops22h 42m
Chicago O'Hare Intl
So 6/16
1 stop29h 19m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Sa 6/15
Nonstop2h 28m
Chicago O'Hare Intl
Mi 6/19
1 stop11h 37m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Mi 9/18
1 stop8h 35m
Chicago O'Hare Intl
Di 9/24
2 stops12h 02m
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
Do 6/20
1 stop15h 37m
Chicago Midway
Do 6/27
2 stops10h 07m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Di 6/11
Nonstop2h 28m
Chicago O'Hare Intl
Sa 6/15
Nonstop2h 26m
No data available for this route at this time. Please check back soon.
Entertainment
Food
Boarding
Comfort
Crew
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.
Entertainment
Food
Boarding
Comfort
Crew
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.
Entertainment
Food
Boarding
Comfort
Crew
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.
Entertainment
Food
Boarding
Comfort
Crew
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.
Entertainment
Food
Boarding
Comfort
Crew
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.
Entertainment
Food
Boarding
Comfort
Crew
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.
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