When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 29 days in advance, which can save you up to 489% on flights from Illinois to Winnipeg compared to booking the week you need them. Waiting 29 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at C$ 459. For sooner than that we have options available in the next 3 days from C$ 1,495.
Flights from Illinois to Winnipeg lean towards being more expensive in July. Prices are generally better when you fly from Illinois to Winnipeg in March, with the cheapest ticket starting at C$ 279.
When flying from Illinois to Winnipeg, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
C$ 390 - C$ 796
Route
Depart
Return
Price
Chicago O'Hare IntlWinnipeg
ORD - YWG
ORDYWG
Chicago O'Hare Intl
Tue 2/7
1 stop17h 45m
Winnipeg
Fri 5/7
1 stop8h 47m
Chicago O'Hare IntlWinnipeg
ORD - YWG
ORDYWG
Chicago O'Hare Intl
Tue 2/7
2 stops20h 42m
Winnipeg
Fri 5/7
1 stop12h 47m
Chicago O'Hare IntlWinnipeg
ORD - YWG
ORDYWG
Chicago O'Hare Intl
Thu 22/8
1 stop29h 17m
Winnipeg
Wed 28/8
1 stop8h 27m
Chicago O'Hare IntlWinnipeg
ORD - YWG
ORDYWG
Chicago O'Hare Intl
Wed 21/8
1 stop17h 43m
Winnipeg
Tue 27/8
1 stop8h 27m
Chicago O'Hare IntlWinnipeg
ORD - YWG
ORDYWG
Chicago O'Hare Intl
Tue 16/7
2 stops15h 23m
Winnipeg
Fri 26/7
1 stop8h 27m
Chicago O'Hare IntlWinnipeg
ORD - YWG
ORDYWG
Chicago O'Hare Intl
Tue 16/7
3 stops17h 27m
Winnipeg
Fri 26/7
1 stop8h 27m
Chicago O'Hare IntlWinnipeg
ORD - YWG
ORDYWG
Chicago O'Hare Intl
Fri 21/6
1 stop6h 52m
Winnipeg
Tue 25/6
1 stop7h 49m
Chicago MidwayWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Wed 21/8
1 stop9h 04m
Winnipeg
Tue 27/8
2 stops10h 30m
Chicago O'Hare IntlWinnipeg
ORD - YWG
ORDYWG
Chicago O'Hare Intl
Mon 1/7
1 stop16h 13m
Winnipeg
Mon 8/7
Nonstop2h 28m
No data available for this route at this time. Please check back soon.
Entertainment
Comfort
Crew
Boarding
Food
Overall
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Entertainment
Comfort
Crew
Boarding
Food
Overall
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Entertainment
Comfort
Crew
Boarding
Food
Overall
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Entertainment
Comfort
Crew
Boarding
Food
Overall
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Entertainment
Comfort
Crew
Boarding
Food
Overall
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Entertainment
Comfort
Crew
Boarding
Food
Overall
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
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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