Popular in | March |
---|---|
Cheapest in | April |
Round-trip from | C$ 358 |
One-way from | C$ 328 |
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$ 811.
The best pricing can be found in the month of April. Prices to Chicago from Winnipeg average C$ 727. You can even find prices in April for less than C$ 727, as users have found deals to Chicago from as low as C$ 470. 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$ 460 - C$ 1,097
Route
Depart
Return
Price
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
Thu 4/7
1 stop12h 49m
Chicago Midway
Wed 10/7
1 stop7h 55m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Fri 24/5
1 stop8h 35m
Chicago O'Hare Intl
Fri 31/5
1 stop9h 45m
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
Mon 24/6
2 stops5h 48m
Chicago Midway
Mon 1/7
1 stop4h 18m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Fri 24/5
1 stop8h 35m
Chicago O'Hare Intl
Fri 31/5
1 stop8h 25m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Thu 13/6
2 stops9h 53m
Chicago O'Hare Intl
Mon 17/6
1 stop7h 34m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Mon 27/5
Nonstop2h 28m
Chicago O'Hare Intl
Sat 1/6
1 stop14h 26m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Sat 1/6
1 stop8h 35m
Chicago O'Hare Intl
Wed 5/6
3 stops28h 24m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Sat 25/5
Nonstop2h 28m
Chicago O'Hare Intl
Wed 29/5
1 stop14h 55m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Sat 1/6
Nonstop2h 28m
Chicago O'Hare Intl
Wed 5/6
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$ 357
February
C$ 415
March
C$ 443
April
C$ 455
May
C$ 535
June
C$ 560
July
C$ 605
August
C$ 617
September
C$ 473
October
C$ 508
November
C$ 462
December
C$ 477
CHI Temperature | -5 - 23 °C |
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Overall
Entertainment
Boarding
Comfort
Food
Crew
Reviews
Terrible flight crew that skipped our row for service multiple times.
Overall
Entertainment
Boarding
Comfort
Food
Crew
Reviews
Terrible flight crew that skipped our row for service multiple times.
Overall
Entertainment
Boarding
Comfort
Food
Crew
Reviews
Terrible flight crew that skipped our row for service multiple times.
Overall
Entertainment
Boarding
Comfort
Food
Crew
Reviews
Terrible flight crew that skipped our row for service multiple times.
Overall
Entertainment
Boarding
Comfort
Food
Crew
Reviews
Terrible flight crew that skipped our row for service multiple times.
Overall
Entertainment
Boarding
Comfort
Food
Crew
Reviews
Terrible flight crew that skipped our row for service multiple times.
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.