Popular in | March |
---|---|
Cheapest in | April |
Average price | C$ 611 |
Round-trip from | C$ 361 |
Monday is generally a great day to depart. Flying on this day could help you save up to 19%.
Find a great deal and save up to 237% by booking at least 24 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Winnipeg to Chicago within the next two weeks, with the cheapest ticket starting at C$ 820.
The best pricing can be found in the month of April. Prices to Chicago from Winnipeg average C$ 734. You can even find prices in April for less than C$ 734, as users have found deals to Chicago from as low as C$ 475. The month of March appears to be one of the more expensive times to travel to Chicago from Winnipeg. Flying in the targeted month can save you up to 16%.
One of the essential ways to save on airfare from Winnipeg to Chicago is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 21% on airfare.
Fly from
Fly to
Budget
C$ 570 - C$ 894
Route
Depart
Return
Price
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Mon 17/6
1 stop8h 27m
Chicago O'Hare Intl
Tue 25/6
2 stops16h 24m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Wed 5/6
2 stops9h 38m
Chicago O'Hare Intl
Fri 7/6
2 stops14h 59m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Tue 4/6
1 stop7h 54m
Chicago O'Hare Intl
Sat 8/6
1 stop8h 10m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Sat 25/5
1 stop8h 35m
Chicago O'Hare Intl
Sun 26/5
2 stops12h 51m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Sat 25/5
1 stop8h 35m
Chicago O'Hare Intl
Sun 26/5
1 stop9h 45m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Mon 27/5
Nonstop2h 28m
Chicago O'Hare Intl
Sat 1/6
1 stop10h 00m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Sat 25/5
Nonstop2h 28m
Chicago O'Hare Intl
Sun 26/5
1 stop17h 06m
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
Fri 3/5
1 stop6h 39m
Chicago Midway
Sun 12/5
1 stop8h 40m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Mon 27/5
Nonstop2h 28m
Chicago O'Hare Intl
Sat 1/6
Nonstop2h 26m
Currently, January is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of C$ 261). Flying from Winnipeg to Chicago in August is currently the most expensive (average of C$ 452). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
January
C$ 360
February
C$ 420
March
C$ 447
April
C$ 472
May
C$ 537
June
C$ 530
July
C$ 606
August
C$ 624
September
C$ 475
October
C$ 511
November
C$ 466
December
C$ 482
CHI Temperature | -5 - 23 °C |
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Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
I love the seamless way that delta ensures that my luggage is on board the plane, I get a notification that it's on board. I love boarding process, orderly and on time. Lots of room in Comfort plus and getting upgraded to first class was everything!
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
I love the seamless way that delta ensures that my luggage is on board the plane, I get a notification that it's on board. I love boarding process, orderly and on time. Lots of room in Comfort plus and getting upgraded to first class was everything!
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
I love the seamless way that delta ensures that my luggage is on board the plane, I get a notification that it's on board. I love boarding process, orderly and on time. Lots of room in Comfort plus and getting upgraded to first class was everything!
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
I love the seamless way that delta ensures that my luggage is on board the plane, I get a notification that it's on board. I love boarding process, orderly and on time. Lots of room in Comfort plus and getting upgraded to first class was everything!
Boarding
Comfort
Crew
Food
Overall
Entertainment
Reviews
I love the seamless way that delta ensures that my luggage is on board the plane, I get a notification that it's on board. I love boarding process, orderly and on time. Lots of room in Comfort plus and getting upgraded to first class was everything!
900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago from Winnipeg today with Cheapflights!
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Winnipeg.
Cheapflights does show flights with no change fees to all users. To see these options for flights from Winnipeg to Chicago, users can toggle the no change fees filter when performing a flight search.
Yes, Cheapflights offers price alerts on Winnipeg to Chicago flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.