Cheap flights from Winnipeg to Chicago

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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)

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?
March
The cheapest time of year to fly to Chicago from Winnipeg is March. The most expensive is August.
What is the cheapest day to fly to Chicago?
Wednesday
The cheapest day of the week is typically Wednesday. The most expensive is typically Monday
When is the cheapest time to fly to Chicago?
in the evening
Winnipeg to Chicago flights are approximately 42% more expensive at noon than in the evening
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?
60 days before
The cheapest time to buy a flight from Winnipeg to Chicago is approximately 60 days before departure
60
Days before departure
0

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
11 Feb.
7:34 a.m.
YWG
Winnipeg airport
6h 03m
1 Stop
MDW
1:37 p.m.
Chicago Midway airport
Delta
12 Feb.
2:12 p.m.
MDW
Chicago Midway airport
4h 03m
1 Stop
YWG
6:15 p.m.
Winnipeg airport
486 C$
Delta
Delta
12 Feb.
12:25 a.m.
YWG
Winnipeg airport
4h 09m
1 Stop
ORD
4:34 a.m.
Chicago O'Hare Intl airport
Delta
13 Feb.
4:44 a.m.
ORD
Chicago O'Hare Intl airport
5h 52m
1 Stop
YWG
10:36 a.m.
Winnipeg airport
486 C$
Delta
Delta
20 May
12:35 p.m.
YWG
Winnipeg airport
4h 36m
1 Stop
ORD
5:11 p.m.
Chicago O'Hare Intl airport
Delta
22 May
2:59 p.m.
ORD
Chicago O'Hare Intl airport
3h 59m
1 Stop
YWG
6:58 p.m.
Winnipeg airport
524 C$
United Airlines
United Airlines
22 Jun.
2:16 a.m.
YWG
Winnipeg airport
2h 27m
ORD
4:43 a.m.
Chicago O'Hare Intl airport
United Airlines
25 Jun.
4:14 a.m.
ORD
Chicago O'Hare Intl airport
3h 34m
1 Stop
YWG
7:48 a.m.
Winnipeg airport
568 C$
Delta
Delta
16 Jun.
5:52 a.m.
YWG
Winnipeg airport
4h 23m
1 Stop
ORD
10:15 a.m.
Chicago O'Hare Intl airport
Delta
21 Jun.
1:15 a.m.
ORD
Chicago O'Hare Intl airport
4h 02m
1 Stop
YWG
5:17 a.m.
Winnipeg airport
565 C$
Delta
Delta
20 May
12:35 p.m.
YWG
Winnipeg airport
4h 36m
1 Stop
ORD
5:11 p.m.
Chicago O'Hare Intl airport
Delta
22 May
2:59 p.m.
ORD
Chicago O'Hare Intl airport
3h 59m
1 Stop
YWG
6:58 p.m.
Winnipeg airport
524 C$

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