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
$324 - $609
Route
Depart
Return
Price
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Wed 5/29
1 stop10h 17m
Chicago O'Hare Intl
Sun 6/2
1 stop17h 16m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Sat 6/15
1 stop8h 10m
Chicago O'Hare Intl
Mon 6/17
1 stop26h 54m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Tue 6/4
2 stops16h 11m
Chicago O'Hare Intl
Sat 6/8
1 stop14h 09m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Tue 5/28
2 stops10h 19m
Chicago O'Hare Intl
Fri 5/31
1 stop7h 09m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Tue 5/28
1 stop7h 47m
Chicago O'Hare Intl
Fri 5/31
1 stop7h 09m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Wed 6/12
1 stop12h 47m
Chicago O'Hare Intl
Thu 6/20
3 stops22h 31m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Tue 6/11
Nonstop2h 28m
Chicago O'Hare Intl
Tue 6/18
1 stop11h 37m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Tue 11/12
Nonstop2h 21m
Chicago O'Hare Intl
Tue 11/26
Nonstop2h 24m
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
Tue 5/28
2 stops9h 12m
Chicago Midway
Fri 5/31
3 stops24h 52m
No data available for this route at this time. Please check back soon.
Boarding
Crew
Food
Overall
Comfort
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.
Boarding
Crew
Food
Overall
Comfort
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.
Boarding
Crew
Food
Overall
Comfort
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.
Boarding
Crew
Food
Overall
Comfort
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.
Boarding
Crew
Food
Overall
Comfort
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.
Boarding
Crew
Food
Overall
Comfort
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.
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