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

Delta is the most popular carrier 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.

$209 Cheap Flights from Chicago Midway Airport to Winnipeg in 2026

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Find the cheapest flights from Chicago Midway Airport to Winnipeg

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 am - 12:40 am

MDW

YWG

18h 40m

2 stops

7:30 am - 7:31 pm

YWG

MDW

12h 01m

1 stop

$400Multiple Airlines

Thu, Apr 16 - Sun, Apr 19

2:19 pm - 6:05 pm

MDW

YWG

27h 46m

2 stops

7:30 am - 10:19 pm

YWG

MDW

14h 49m

1 stop

$407Multiple Airlines

Mon, Mar 2 - Fri, Mar 6

5:16 pm - 12:40 am

MDW

YWG

31h 24m

2 stops

8:05 pm - 10:05 am

YWG

MDW

14h 00m

1 stop

$472Multiple Airlines

Thu, Mar 5 - Thu, Mar 12

5:16 pm - 3:09 pm

MDW

YWG

21h 53m

1 stop

8:05 pm - 10:05 am

YWG

MDW

14h 00m

1 stop

$475Multiple Airlines

Thu, Mar 5 - Thu, Mar 12

9:34 am - 12:35 am

MDW

YWG

15h 01m

2 stops

6:40 am - 6:40 pm

YWG

MDW

12h 00m

1 stop

$533WestJet

Thu, Mar 5 - Sun, Mar 15

10:43 am - 3:09 pm

MDW

YWG

28h 26m

1 stop

11:55 am - 6:36 pm

YWG

MDW

6h 41m

1 stop

$537WestJet

Thu, Apr 16 - Sun, Apr 19

9:34 am - 12:39 am

MDW

YWG

15h 05m

2 stops

5:00 am - 5:54 pm

YWG

MDW

12h 54m

2 stops

$544WestJet

Thu, Mar 5 - Thu, Mar 12

9:30 am - 7:09 pm

MDW

YWG

9h 39m

2 stops

5:00 am - 12:29 pm

YWG

MDW

7h 29m

2 stops

$546WestJet

Tue, Mar 10 - Tue, Mar 17

9:34 am - 12:35 am

MDW

YWG

15h 01m

2 stops

5:00 am - 5:54 pm

YWG

MDW

12h 54m

2 stops

$568WestJet

Thu, Mar 5 - Sun, Mar 15

7:20 pm - 11:01 am

MDW

YWG

15h 41m

1 stop

5:20 pm - 1:25 pm

YWG

MDW

20h 05m

1 stop

$580WestJet

Tue, Mar 10 - Tue, Mar 17

WestJet flights from Chicago Midway Airport to Winnipeg

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

WestJet

Mar 23

MDW2:05 pmChicago Midway

9h 30m

1 stop

YWG11:35 pmWinnipeg

Mar 30

YWG6:40 amWinnipeg

12h 00m

1 stop

MDW6:40 pmChicago Midway

$492

WestJet

Mar 23

MDW2:05 pmChicago Midway

9h 30m

1 stop

YWG11:35 pmWinnipeg

Mar 30

YWG8:05 pmWinnipeg

16h 24m

2 stops

MDW12:29 pmChicago Midway

$516

WestJet

Mar 5

MDW9:34 amChicago Midway

15h 01m

2 stops

YWG12:35 amWinnipeg

Mar 15

YWG6:40 amWinnipeg

12h 00m

1 stop

MDW6:40 pmChicago Midway

$533

Porter Airlines flights from Chicago Midway Airport to Winnipeg

Our best Porter Airlines deals on Chicago Midway Airport to Winnipeg flight tickets

Porter Airlines

Feb 17

MDW11:05 amChicago Midway

24h 08m

3 stops

YWG11:13 amWinnipeg

Feb 20

YWG4:25 pmWinnipeg

19h 30m

3 stops

MDW11:55 amChicago Midway

$1,238

Porter Airlines

Feb 17

MDW11:05 amChicago Midway

24h 08m

2 stops

YWG11:13 amWinnipeg

Feb 20

YWG4:25 pmWinnipeg

19h 30m

3 stops

MDW11:55 amChicago Midway

$1,340

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

Thu 4/16

6:00 am-12:40 am

2 stops18h 40m

Winnipeg

Sun 4/19

7:30 am-7:31 pm

1 stop12h 01m

$400

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 3/2

2:19 pm-6:05 pm

2 stops27h 46m

Winnipeg

Fri 3/6

7:30 am-10:19 pm

1 stop14h 49m

$407

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 3/5

5:16 pm-12:40 am

2 stops31h 24m

Winnipeg

Thu 3/12

8:05 pm-10:05 am

1 stop14h 00m

$472

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 3/5

5:16 pm-3:09 pm

1 stop21h 53m

Winnipeg

Thu 3/12

8:05 pm-10:05 am

1 stop14h 00m

$475

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 3/5

9:34 am-12:35 am

2 stops15h 01m

Winnipeg

Sun 3/15

6:40 am-6:40 pm

1 stop12h 00m

$533

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 4/16

10:43 am-3:09 pm

1 stop28h 26m

Winnipeg

Sun 4/19

11:55 am-6:36 pm

1 stop6h 41m

$537

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 3/5

9:34 am-12:39 am

2 stops15h 05m

Winnipeg

Thu 3/12

5:00 am-5:54 pm

2 stops12h 54m

$544

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 3/10

9:30 am-7:09 pm

2 stops9h 39m

Winnipeg

Tue 3/17

5:00 am-12:29 pm

2 stops7h 29m

$546

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 3/5

9:34 am-12:35 am

2 stops15h 01m

Winnipeg

Sun 3/15

5:00 am-5:54 pm

2 stops12h 54m

$568

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 3/10

7:20 pm-11:01 am

1 stop15h 41m

Winnipeg

Tue 3/17

5:20 pm-1:25 pm

1 stop20h 05m

$580

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 $584. 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 $675.

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 in the morning when prices are $699 on average. Flights to Winnipeg from Chicago Midway Airport in the morning 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

Fastest flight time	4h 42m
Direct flights	None

The fastest flight from Chicago Midway Airport to Winnipeg takes 4h 42m

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 4h 42m 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.

Scanterbury

Portage la Prairie

Selkirk

Morden

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Winnipeg. momondo saves you time and could save you money on your trip.

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.