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Flights from Winnipeg to Chicago – Airlines & connecting routes

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YWG to MDW flights and routes map YWG to MDW – All flight route options from Winnipeg International, Canada to Chicago Midway International, Illinois, USA. These flights are operated by Delta Air Lines & WestJet through 1 different flight connections. The shortest flight time is 4 hours and 31 minutes. See the full flight schedule and time table, including departure times, airlines and stopover details to find the best option for you.

From
To
Canada YWG Winnipeg Winnipeg, MB, Canada
USA MDW Chicago Midway , IL, USA
YWG
Winnipeg
CanadaWinnipeg, MB, Canada
Chicago Midway
USAChicago, IL, USA
MDW
No direct flights found
2 routes with 1 stop found »
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1 stop route options with the same airline:

Duration

Via Minneapolis MSP
1 stop with Delta Air Lines. 3 flights per day.

SHOW SCHEDULE
5h 13m

Via Minneapolis MSP
1 stop with Delta Air Lines.
5h 13m
3 flights per day.
SHOW SCHEDULE

1 stop route options with codeshare or different airlines:

Duration

Via Minneapolis MSP With WestJet & Delta Air Lines 3 flights per day.
CODESHARE

SHOW SCHEDULE
4h 31m

Via Minneapolis MSP
4h 31m
With WestJet & Delta Air Lines 3 flights per day.
CODESHARE
SHOW SCHEDULE
SELECT DATE & CHECK PRICE

Other flight options

Check out these routes. They have daily flights from Winnipeg International and connections to Chicago:

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Winnipeg to Chicago flights

This route is operated by one airline and has approximately 26 flights per week. You will be doing a stopover in Minneapolis (Airport code: MSP).

Are there any non-stop flights from YWG to MDW?

There are no direct or non-stop flights from Winnipeg International, YWG to Chicago Midway International, MDW.

Winnipeg to Chicago with Delta Air Lines

If you fly from Winnipeg with Delta Air Lines you will do a stopover in Minneapolis, MSP before reaching Chicago. This flight trip will take 5 hours and 13 minutes and you can fly every weekday with departures at 6:00 am, 8:00 am or 12 noon. Delta Air Lines is a member of SkyTeam.

Distance & flight times: Winnipeg International to Midway International Airport

The flight time between YWG and MDW is 5 hours and 13 minutes.

ViaTotal flight timeLayover timeDistance
MSP Minneapolis5h 13m3h 8m746 miles (1200 km)
The flight times and layover times in the table above are approximate and may vary depending on flight number, aircraft, airline, weather, and time of day.
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Departing from Winnipeg International
Winnipeg - Chicago route map and flight paths
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From Winnipeg to USA

Below is a list of other destinations to USA from Winnipeg International with either direct flights or 1 stop connections.

From Canada to Chicago

Below is a list of other cities in Canada with flights to Chicago with either non-stop or connecting flights.

Via Minneapolis. A flight from Winnipeg (YWG) to Chicago (MDW) via Minneapolis will take approximately 5 hours and 13 minutes.

You will be flying with Delta Air Lines from Winnipeg to Chicago.

The flight time between Winnipeg (YWG) and Chicago Midway International (MDW) via Minneapolis St Paul International, MSP is 5 hours and 13 minutes.

No. But you can still purchase a 1 stop flight via Minneapolis to Chicago (MDW).

A codeshare agreement means that cooperating airlines are able to sell seats on each other’s flights. This means that you are able to travel to more destinations than your airline of choice normally offers. Codeshare flights are also beneficial because of the seamless transits you can get with connecting flights from the same airline. The downside of choosing a codeshare flight can be that you in some cases can’t upgrade codeshare flights or use elite benefits.

A connecting or transit flight means that you reach your final destination through two or more flights – in other words a non-direct flight. You will change to a new aircraft after your first flight, this may include moving to another terminal at the airport aswell. The time required to transfer passengers and luggage between flights is called Minimum Connecting Time (MCT) and are always taken into account here on Flightroutes.com.

If you bought your whole flight on a single ticket, the airline will book you on the next available connecting flight.

With connecting flights, checked in luggage is most commonly forwarded to your final destination when buying a single ticket for both flights.

If you miss your connecting flight due to circumstances outside your control such as your first flight being delayed, you should turn to your airline who will provide you with a seat on the next available flight. This is usually done free of charge, and only applies if you purchased your trip as one ticket. If the next connecting flight is the following day, the airline usually provides accommodation and meals.
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