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

Porter Airlines 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.

$137 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 - 10:10 pm

MDW

YWG

16h 10m

2 stops

4:25 pm - 9:45 am

YWG

MDW

17h 20m

1 stop

$349Multiple Airlines

Thu, May 7 - Sun, May 10

6:00 am - 10:10 pm

MDW

YWG

16h 10m

2 stops

6:05 pm - 9:45 am

YWG

MDW

15h 40m

1 stop

$361Multiple Airlines

Thu, May 7 - Sun, May 10

3:20 pm - 3:19 pm

MDW

YWG

23h 59m

1 stop

7:00 pm - 9:45 am

YWG

MDW

14h 45m

1 stop

$399Porter Airlines

Thu, May 7 - Sun, May 10

3:20 pm - 9:45 am

MDW

YWG

18h 25m

1 stop

6:05 pm - 9:45 am

YWG

MDW

15h 40m

1 stop

$427Multiple Airlines

Thu, May 7 - Sun, May 10

3:20 pm - 12:55 am

MDW

YWG

9h 35m

1 stop

8:45 pm - 9:40 am

YWG

MDW

12h 55m

1 stop

$440Multiple Airlines

Fri, Jun 5 - Sun, Jun 7

7:30 am - 8:40 am

MDW

YWG

25h 10m

2 stops

8:05 pm - 3:20 pm

YWG

MDW

19h 15m

1 stop

$444Multiple Airlines

Wed, Apr 15 - Thu, Apr 16

10:30 am - 7:49 pm

MDW

YWG

9h 19m

1 stop

7:00 pm - 9:45 am

YWG

MDW

14h 45m

1 stop

$445Porter Airlines

Thu, May 7 - Sun, May 10

11:00 am - 11:32 am

MDW

YWG

24h 32m

1 stop

8:05 pm - 3:20 pm

YWG

MDW

19h 15m

1 stop

$452Multiple Airlines

Wed, Apr 15 - Thu, Apr 16

3:20 pm - 12:55 am

MDW

YWG

9h 35m

1 stop

9:05 pm - 2:35 pm

YWG

MDW

17h 30m

2 stops

$474Multiple Airlines

Fri, Jun 5 - Sun, Jun 7

6:00 am - 12:40 am

MDW

YWG

18h 40m

2 stops

8:05 pm - 12:10 pm

YWG

MDW

16h 05m

1 stop

$490Multiple Airlines

Thu, Apr 16 - Fri, Apr 17

Porter Airlines flights from Chicago Midway Airport to Winnipeg

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

Porter Airlines

May 7

MDW3:20 pmChicago Midway

23h 59m

1 stop

YWG3:19 pmWinnipeg

May 10

YWG7:00 pmWinnipeg

14h 45m

1 stop

MDW9:45 amChicago Midway

$399

Porter Airlines

May 7

MDW10:30 amChicago Midway

9h 19m

1 stop

YWG7:49 pmWinnipeg

May 10

YWG7:00 pmWinnipeg

14h 45m

1 stop

MDW9:45 amChicago Midway

$445

Porter Airlines

May 11

MDW3:20 pmChicago Midway

23h 58m

2 stops

YWG3:18 pmWinnipeg

Jun 1

YWG4:15 pmWinnipeg

17h 25m

2 stops

MDW9:40 amChicago Midway

$623

WestJet flights from Chicago Midway Airport to Winnipeg

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

WestJet

May 7

MDW1:22 pmChicago Midway

11h 33m

2 stops

YWG12:55 amWinnipeg

May 10

YWG5:41 pmWinnipeg

24h 15m

1 stop

MDW5:56 pmChicago Midway

$588

WestJet

Apr 27

MDW9:27 amChicago Midway

15h 28m

2 stops

YWG12:55 amWinnipeg

Apr 28

YWG11:55 amWinnipeg

6h 41m

1 stop

MDW6:36 pmChicago Midway

$604

WestJet

Jul 23

MDW9:20 amChicago Midway

15h 35m

2 stops

YWG12:55 amWinnipeg

Jul 31

YWG7:45 amWinnipeg

10h 40m

2 stops

MDW6:25 pmChicago Midway

$607

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

Cheapest round-trip

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 5/7

6:00 am-10:10 pm

2 stops16h 10m

Winnipeg

Sun 5/10

4:25 pm-9:45 am

1 stop17h 20m

$349

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 5/7

6:00 am-10:10 pm

2 stops16h 10m

Winnipeg

Sun 5/10

6:05 pm-9:45 am

1 stop15h 40m

$361

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 5/7

3:20 pm-3:19 pm

1 stop23h 59m

Winnipeg

Sun 5/10

7:00 pm-9:45 am

1 stop14h 45m

$399

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 5/7

3:20 pm-9:45 am

1 stop18h 25m

Winnipeg

Sun 5/10

6:05 pm-9:45 am

1 stop15h 40m

$427

Quickest round-trip

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 6/5

3:20 pm-12:55 am

1 stop9h 35m

Winnipeg

Sun 6/7

8:45 pm-9:40 am

1 stop12h 55m

$440

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 4/15

7:30 am-8:40 am

2 stops25h 10m

Winnipeg

Thu 4/16

8:05 pm-3:20 pm

1 stop19h 15m

$444

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 5/7

10:30 am-7:49 pm

1 stop9h 19m

Winnipeg

Sun 5/10

7:00 pm-9:45 am

1 stop14h 45m

$445

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 4/15

11:00 am-11:32 am

1 stop24h 32m

Winnipeg

Thu 4/16

8:05 pm-3:20 pm

1 stop19h 15m

$452

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 6/5

3:20 pm-12:55 am

1 stop9h 35m

Winnipeg

Sun 6/7

9:05 pm-2:35 pm

2 stops17h 30m

$474

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 4/16

6:00 am-12:40 am

2 stops18h 40m

Winnipeg

Fri 4/17

8:05 pm-12:10 pm

1 stop16h 05m

$490

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 Wednesday when prices can be found for as low as $509. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday 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 $689.

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 $756 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.

Selkirk

Portage la Prairie

Morden

Why use momondo?

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.