What is the cheapest airline that flies from Chicago Midway to Winnipeg?

WestJet and Porter Airlines are the most popular carriers operating from Chicago Midway to Winnipeg

When did momondo last update prices for flights from Chicago Midway Airport to Winnipeg Airport?

Prices for flights from Chicago Midway Airport to Winnipeg Airport are refreshed on a daily basis.

How old do you have to be to fly from Chicago Midway Airport to Winnipeg Airport?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Winnipeg Airport.

What documentation or ID do you need to fly to Winnipeg Airport?

The travel and health documents you'll need for your trip to Winnipeg Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Winnipeg Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$79 Cheap Flights from Chicago Midway Airport to Winnipeg in 2025/26

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Find the cheapest flights from Chicago Midway Airport to Winnipeg

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One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

2:49 pm - 3:07 pmMDW-YWG

24h 18m1 stop

7:30 am - 6:12 pmYWG-MDW

10h 42m1 stop

$196Multiple Airlines

Find Deal

Tue, Dec 2 - Sun, Dec 7

2:49 pm - 3:07 pmMDW-YWG

24h 18m1 stop

9:00 pm - 8:46 amYWG-MDW

35h 46m2 stops

$198Multiple Airlines

Find Deal

Tue, Dec 2 - Mon, Dec 8

6:15 am - 12:41 amMDW-YWG

18h 26m2 stops

7:30 am - 6:12 pmYWG-MDW

10h 42m1 stop

$201Multiple Airlines

Find Deal

Thu, Dec 4 - Sun, Dec 7

6:15 am - 12:41 amMDW-YWG

18h 26m2 stops

7:30 am - 6:12 pmYWG-MDW

10h 42m1 stop

$206Multiple Airlines

Find Deal

Fri, Dec 5 - Sun, Dec 7

7:23 pm - 3:07 pmMDW-YWG

19h 44m1 stop

7:30 am - 6:12 pmYWG-MDW

10h 42m1 stop

$207Multiple Airlines

Find Deal

Thu, Dec 4 - Sun, Dec 7

6:00 am - 11:44 pmMDW-YWG

17h 44m2 stops

5:45 pm - 11:55 amYWG-MDW

18h 10m2 stops

$462Delta

Find Deal

Sat, Dec 6 - Tue, Dec 9

6:00 am - 11:44 pmMDW-YWG

17h 44m2 stops

6:40 am - 11:47 pmYWG-MDW

17h 07m2 stops

$495Delta

Find Deal

Wed, Dec 3 - Tue, Dec 9

10:49 am - 12:42 amMDW-YWG

13h 53m2 stops

12:35 pm - 6:18 pmYWG-MDW

5h 43m1 stop

$504WestJet

Find Deal

Tue, Dec 2 - Tue, Dec 9

9:41 am - 12:42 amMDW-YWG

15h 01m2 stops

5:00 am - 8:54 amYWG-MDW

27h 54m2 stops

$518WestJet

Find Deal

Mon, Nov 24 - Thu, Nov 27

6:00 am - 11:44 pmMDW-YWG

17h 44m2 stops

5:45 pm - 11:47 pmYWG-MDW

30h 02m2 stops

$522Delta

Find Deal

Wed, Dec 3 - Sun, Dec 7

Delta flights from Chicago Midway Airport to Winnipeg

Our best Delta deals on Chicago Midway Airport to Winnipeg flight tickets

Delta

Dec 6

MDW6:00 amChicago Midway

17h 44m

2 stops

YWG11:44 pmWinnipeg

Dec 9

YWG5:45 pmWinnipeg

18h 10m

2 stops

MDW11:55 amChicago Midway

$462

Find similar

Delta

Dec 3

MDW6:00 amChicago Midway

17h 44m

2 stops

YWG11:44 pmWinnipeg

Dec 9

YWG6:40 amWinnipeg

17h 07m

2 stops

MDW11:47 pmChicago Midway

$495

Find similar

Delta

Dec 3

MDW6:00 amChicago Midway

17h 44m

2 stops

YWG11:44 pmWinnipeg

Dec 7

YWG5:45 pmWinnipeg

30h 02m

2 stops

MDW11:47 pmChicago Midway

$522

Find similar

WestJet flights from Chicago Midway Airport to Winnipeg

Our best WestJet deals on Chicago Midway Airport to Winnipeg flight tickets

WestJet

Dec 2

MDW10:49 amChicago Midway

13h 53m

2 stops

YWG12:42 amWinnipeg

Dec 9

YWG12:35 pmWinnipeg

5h 43m

1 stop

MDW6:18 pmChicago Midway

$504

Find similar

WestJet

Nov 24

MDW9:41 amChicago Midway

15h 01m

2 stops

YWG12:42 amWinnipeg

Nov 27

YWG5:00 amWinnipeg

27h 54m

2 stops

MDW8:54 amChicago Midway

$518

Find similar

WestJet

Nov 13

MDW10:47 amChicago Midway

28h 20m

1 stop

YWG3:07 pmWinnipeg

Nov 16

YWG7:30 amWinnipeg

26h 22m

1 stop

MDW9:52 amChicago Midway

$821

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 12/2

2:49 pm-3:07 pm

1 stop24h 18m

Winnipeg

Sun 12/7

7:30 am-6:12 pm

1 stop10h 42m

$196

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 12/2

2:49 pm-3:07 pm

1 stop24h 18m

Winnipeg

Mon 12/8

9:00 pm-8:46 am

2 stops35h 46m

$198

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 12/4

6:15 am-12:41 am

2 stops18h 26m

Winnipeg

Sun 12/7

7:30 am-6:12 pm

1 stop10h 42m

$201

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 12/5

6:15 am-12:41 am

2 stops18h 26m

Winnipeg

Sun 12/7

7:30 am-6:12 pm

1 stop10h 42m

$206

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 12/4

7:23 pm-3:07 pm

1 stop19h 44m

Winnipeg

Sun 12/7

7:30 am-6:12 pm

1 stop10h 42m

$207

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 12/6

6:00 am-11:44 pm

2 stops17h 44m

Winnipeg

Tue 12/9

5:45 pm-11:55 am

2 stops18h 10m

$462

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 12/3

6:00 am-11:44 pm

2 stops17h 44m

Winnipeg

Tue 12/9

6:40 am-11:47 pm

2 stops17h 07m

$495

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 12/2

10:49 am-12:42 am

2 stops13h 53m

Winnipeg

Tue 12/9

12:35 pm-6:18 pm

1 stop5h 43m

$504

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 11/24

9:41 am-12:42 am

2 stops15h 01m

Winnipeg

Thu 11/27

5:00 am-8:54 am

2 stops27h 54m

$518

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 12/3

6:00 am-11:44 pm

2 stops17h 44m

Winnipeg

Sun 12/7

5:45 pm-11:47 pm

2 stops30h 02m

$522

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago Midway Airport to Winnipeg

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 ticket for your trip

Prices

Airlines

What is the cheapest day to depart on your flight to Winnipeg?

The cheapest day to depart on your flight to Winnipeg is on a Saturday when prices can be found for as low as $562. This is often the case because there is less demand to fly during this day of the week. On the other hand, Wednesday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $645.

What is the cheapest time of day to depart on your flight to Winnipeg?

The cheapest time of day to fly to Winnipeg is in the evening when flights can be purchased for as low as $543. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $632 on average. Flights to Winnipeg from Chicago Midway Airport at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.

When to book flights from Chicago Midway Airport to Winnipeg

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Winnipeg according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago Midway Airport to Winnipeg (MDW to YWG) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Winnipeg

Direct flights	None

There are no direct flights from Chicago Midway Airport to Winnipeg. There are no popular flight routes from Chicago Midway Airport to Winnipeg.

Search flight deals

How far is Chicago Midway to Winnipeg by plane?
Winnipeg is 717.8 mi away from Chicago Midway. Typically, this will take 8h 52m by plane in normal conditions.
When did momondo last update prices for flights from Chicago Midway Airport to Winnipeg Airport?
Prices for flights from Chicago Midway Airport to Winnipeg Airport are refreshed on a daily basis.
How old do you have to be to fly from Chicago Midway Airport to Winnipeg Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Winnipeg Airport.
What documentation or ID do you need to fly to Winnipeg Airport?
The travel and health documents you'll need for your trip to Winnipeg Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Winnipeg Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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Selkirk

Morden

Portage la Prairie

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Why should I use momondo to find a flight deal from Chicago to Winnipeg?

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Can I find flights from Chicago to Winnipeg with flexible booking policies on momondo?

All flight searches from Chicago to Winnipeg on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Winnipeg?

momondo provides multiple filters to help you find the best flight to Winnipeg from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Winnipeg right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Winnipeg flights. All you need is a valid email address and we will do the rest; it is that quick and easy.