Cheap flights from Winnipeg to Chicago

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Winnipeg to Chicago flight comparison made easy

Below you can see the best fares for your route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Winnipeg to Chicago by changing tabs
Quickest
Cheapest
Delta
Delta
13 Dec.
YWG
11:20 a.m.
Winnipeg airport
4h 41m
1 Stop
4:01 p.m.
ORD
Chicago O'Hare Intl airport
Delta
16 Dec.
ORD
7:11 a.m.
Chicago O'Hare Intl airport
3h 24m
1 Stop
10:35 a.m.
YWG
Winnipeg airport
424 CAD
Delta
Delta
09 Dec.
YWG
8:30 a.m.
Winnipeg airport
4h 47m
1 Stop
1:17 p.m.
ORD
Chicago O'Hare Intl airport
Delta
11 Dec.
ORD
7:11 a.m.
Chicago O'Hare Intl airport
3h 24m
1 Stop
10:35 a.m.
YWG
Winnipeg airport
451 CAD
Delta
Delta
08 Jan.
YWG
11:33 a.m.
Winnipeg airport
4h 40m
1 Stop
4:13 p.m.
ORD
Chicago O'Hare Intl airport
Delta
12 Jan.
ORD
12:10 a.m.
Chicago O'Hare Intl airport
4h 26m
1 Stop
4:36 a.m.
YWG
Winnipeg airport
476 CAD
Delta
Delta
13 Dec.
YWG
11:20 a.m.
Winnipeg airport
4h 41m
1 Stop
4:01 p.m.
ORD
Chicago O'Hare Intl airport
Delta
16 Dec.
ORD
7:11 a.m.
Chicago O'Hare Intl airport
3h 24m
1 Stop
10:35 a.m.
YWG
Winnipeg airport
424 CAD
Delta
Delta
09 Dec.
YWG
8:30 a.m.
Winnipeg airport
4h 47m
1 Stop
1:17 p.m.
ORD
Chicago O'Hare Intl airport
Delta
11 Dec.
ORD
7:11 a.m.
Chicago O'Hare Intl airport
3h 24m
1 Stop
10:35 a.m.
YWG
Winnipeg airport
451 CAD
Delta
Delta
06 Apr.
YWG
12:40 p.m.
Winnipeg airport
4h 35m
1 Stop
5:15 p.m.
MDW
Chicago Midway airport
Delta
30 Apr.
MDW
1:10 a.m.
Chicago Midway airport
4h 09m
1 Stop
5:19 a.m.
YWG
Winnipeg airport
502 CAD

How to get the cheapest flight from Winnipeg to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight for your trip
What is the cheapest month to fly to Chicago?
January
The cheapest time of year to fly to Chicago from Winnipeg is January. The most expensive is December.
What is the cheapest day to fly to Chicago?
Tuesday
The cheapest day of the week is typically Tuesday. The most expensive is typically Monday
When is the cheapest time to fly to Chicago?
in the afternoon
Winnipeg to Chicago flights are approximately 16% more expensive at noon than in the afternoon
What is the cheapest airline that flies to Chicago?
WestJet
WestJet, Delta, and Air Canada are the most popular carriers operating from Winnipeg to Chicago
What is the cheapest route?
Winnipeg - Chicago O'Hare Intl
Fly from Winnipeg to Chicago O'Hare Intl for the best Winnipeg - Chicago flight prices
When is the cheapest time to book a flight to Chicago?
43 days before
The cheapest time to buy a flight from Winnipeg to Chicago is approximately 43 days before departure
60
Days before departure
0

Flight information for Winnipeg to Chicago

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Chicago
Fastest flight time 2h 27m The fastest flight from Winnipeg to Chicago takes 2h 27m.
Direct flights Every day Direct flights go from Winnipeg to Chicago every day.
Airports in Chicago 3 airports There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

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