Cheap flights from Winnipeg to Chicago

Round-trip
Economy
Winnipeg (YWG)
Chicago (CHI)
Tue. 8/9
Tue. 15/9
Any month
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Flight information for Winnipeg to Chicago
(YWG to CHI)

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Chicago
Best price found 609 C$ The best flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is 609 C$
Fastest flight time 7h 47m The fastest flight from Winnipeg to Chicago takes 7h 47m.
Direct flights None There are no direct flights from Winnipeg to Chicago. Popular non-direct routes for this connection are Winnipeg - Chicago O'Hare Intl and Winnipeg - Chicago Midway.
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 43% 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 Midway
Fly from Winnipeg to Chicago Midway for the best Winnipeg - Chicago flight prices
When is the cheapest time to book a flight to Chicago?
45 days before
The cheapest time to buy a flight from Winnipeg to Chicago is approximately 45 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
Cheapest
Best
Quickest
Lufthansa
15 Sep.
YWG
Winnipeg
6h 03m
1 stop
ORD
Chicago O'Hare Intl
18 Sep.
ORD
Chicago O'Hare Intl
2h 34m
YWG
Winnipeg
Aer Lingus
15 Sep.
YWG
Winnipeg
2h 27m
ORD
Chicago O'Hare Intl
18 Sep.
ORD
Chicago O'Hare Intl
7h 33m
1 stop
YWG
Winnipeg
Multiple Airlines
6 Aug.
YWG
Winnipeg
9h 05m
2 stops
ORD
Chicago O'Hare Intl
27 Aug.
ORD
Chicago O'Hare Intl
8h 01m
1 stop
YWG
Winnipeg

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