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

Porter Airlines and WestJet 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.

$235 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.

10:15 am - 9:45 am

MDW

YWG

23h 30m

1 stop

6:05 pm - 9:40 am

YWG

MDW

15h 35m

1 stop

$402Multiple Airlines

Tue, Jun 16 - Mon, Jun 22

10:15 am - 9:45 am

MDW

YWG

23h 30m

1 stop

8:45 pm - 9:40 am

YWG

MDW

12h 55m

1 stop

$408Multiple Airlines

Wed, Jun 17 - Sun, Jun 21

10:15 am - 7:49 pm

MDW

YWG

9h 34m

1 stop

8:45 pm - 9:40 am

YWG

MDW

12h 55m

1 stop

$413Porter Airlines

Tue, Jun 16 - Sun, Jun 21

10:15 am - 7:49 pm

MDW

YWG

9h 34m

1 stop

5:10 pm - 9:40 am

YWG

MDW

16h 30m

1 stop

$421Multiple Airlines

Tue, Jun 16 - Sat, Jun 20

10:15 am - 12:55 am

MDW

YWG

14h 40m

1 stop

9:05 pm - 11:09 am

YWG

MDW

14h 04m

2 stops

$422Multiple Airlines

Thu, Jun 4 - Sun, Jun 7

3:20 pm - 9:45 am

MDW

YWG

18h 25m

1 stop

6:05 pm - 9:40 am

YWG

MDW

15h 35m

1 stop

$427Multiple Airlines

Mon, Jun 15 - Mon, Jun 22

10:15 am - 7:49 pm

MDW

YWG

9h 34m

1 stop

4:25 pm - 9:40 am

YWG

MDW

17h 15m

1 stop

$428Multiple Airlines

Tue, Jun 16 - Wed, Jun 17

3:20 pm - 9:45 am

MDW

YWG

18h 25m

1 stop

8:45 pm - 9:40 am

YWG

MDW

12h 55m

1 stop

$432Multiple Airlines

Thu, Jun 18 - Tue, Jun 23

3:20 pm - 9:45 am

MDW

YWG

18h 25m

1 stop

8:45 pm - 9:40 am

YWG

MDW

12h 55m

1 stop

$433Multiple Airlines

Mon, Jun 15 - Sun, Jun 21

10:15 am - 7:49 pm

MDW

YWG

9h 34m

1 stop

8:45 pm - 9:40 am

YWG

MDW

12h 55m

1 stop

$434Porter Airlines

Wed, Jun 17 - Fri, Jun 19

WestJet flights from Chicago Midway Airport to Winnipeg

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

WestJet

Jun 5

MDW6:36 pmChicago Midway

19h 49m

2 stops

YWG2:25 pmWinnipeg

Jun 7

YWG12:46 pmWinnipeg

5h 32m

1 stop

MDW6:18 pmChicago Midway

$514

WestJet

Jun 6

MDW10:45 amChicago Midway

14h 10m

2 stops

YWG12:55 amWinnipeg

Jun 7

YWG12:46 pmWinnipeg

5h 32m

1 stop

MDW6:18 pmChicago Midway

$539

WestJet

May 25

MDW7:13 pmChicago Midway

15h 41m

1 stop

YWG10:54 amWinnipeg

May 28

YWG5:41 pmWinnipeg

24h 15m

1 stop

MDW5:56 pmChicago Midway

$738

Porter Airlines flights from Chicago Midway Airport to Winnipeg

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

Porter Airlines

Jun 16

MDW10:15 amChicago Midway

9h 34m

1 stop

YWG7:49 pmWinnipeg

Jun 21

YWG8:45 pmWinnipeg

12h 55m

1 stop

MDW9:40 amChicago Midway

$413

Porter Airlines

Jun 17

MDW10:15 amChicago Midway

9h 34m

1 stop

YWG7:49 pmWinnipeg

Jun 19

YWG8:45 pmWinnipeg

12h 55m

1 stop

MDW9:40 amChicago Midway

$434

Porter Airlines

Jun 19

MDW10:25 amChicago Midway

9h 24m

1 stop

YWG7:49 pmWinnipeg

Jun 23

YWG8:45 pmWinnipeg

12h 55m

1 stop

MDW9:40 amChicago Midway

$438

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

Tue 6/16

10:15 am-9:45 am

1 stop23h 30m

Winnipeg

Mon 6/22

6:05 pm-9:40 am

1 stop15h 35m

$402

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 6/17

10:15 am-9:45 am

1 stop23h 30m

Winnipeg

Sun 6/21

8:45 pm-9:40 am

1 stop12h 55m

$408

Quickest round-trip

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 6/16

10:15 am-7:49 pm

1 stop9h 34m

Winnipeg

Sun 6/21

8:45 pm-9:40 am

1 stop12h 55m

$413

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 6/16

10:15 am-7:49 pm

1 stop9h 34m

Winnipeg

Sat 6/20

5:10 pm-9:40 am

1 stop16h 30m

$421

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 6/4

10:15 am-12:55 am

1 stop14h 40m

Winnipeg

Sun 6/7

9:05 pm-11:09 am

2 stops14h 04m

$422

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 6/15

3:20 pm-9:45 am

1 stop18h 25m

Winnipeg

Mon 6/22

6:05 pm-9:40 am

1 stop15h 35m

$427

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 6/16

10:15 am-7:49 pm

1 stop9h 34m

Winnipeg

Wed 6/17

4:25 pm-9:40 am

1 stop17h 15m

$428

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 6/18

3:20 pm-9:45 am

1 stop18h 25m

Winnipeg

Tue 6/23

8:45 pm-9:40 am

1 stop12h 55m

$432

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 6/15

3:20 pm-9:45 am

1 stop18h 25m

Winnipeg

Sun 6/21

8:45 pm-9:40 am

1 stop12h 55m

$433

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 6/17

10:15 am-7:49 pm

1 stop9h 34m

Winnipeg

Fri 6/19

8:45 pm-9:40 am

1 stop12h 55m

$434

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 Tuesday 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, 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 $1,074.

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 $585. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $762 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 13m
Direct flights	None

The fastest flight from Chicago Midway Airport to Winnipeg takes 4h 13m

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

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Frequently asked questions about flying from Chicago Midway Airport to Winnipeg

How far is Chicago Midway to Winnipeg by plane?
Winnipeg is 717.8 mi away from Chicago Midway. Typically, this will take 4h 13m 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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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.