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.

$197 Cheap Flights from Chicago Midway Airport to Winnipeg in 2026

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.

3:20 pm - 5:58 pm

MDW

YWG

26h 38m

2 stops

6:05 pm - 9:40 am

YWG

MDW

15h 35m

1 stop

$382Multiple Airlines

Fri, Jul 17 - Fri, Jul 24

3:15 pm - 9:45 am

MDW

YWG

18h 30m

1 stop

7:45 am - 9:45 am

YWG

MDW

26h 00m

1 stop

$389Multiple Airlines

Wed, Aug 5 - Sun, Aug 9

3:20 pm - 12:55 am

MDW

YWG

9h 35m

1 stop

6:05 pm - 9:40 am

YWG

MDW

15h 35m

1 stop

$393Multiple Airlines

Fri, Jul 17 - Fri, Jul 24

3:20 pm - 8:40 am

MDW

YWG

17h 20m

1 stop

11:15 am - 9:40 am

YWG

MDW

22h 25m

2 stops

$398Multiple Airlines

Tue, Jul 14 - Sun, Jul 19

10:25 am - 8:40 am

MDW

YWG

22h 15m

1 stop

6:05 pm - 9:40 am

YWG

MDW

15h 35m

1 stop

$405Multiple Airlines

Tue, Jul 14 - Sun, Jul 19

3:15 pm - 9:45 am

MDW

YWG

18h 30m

1 stop

6:05 pm - 9:40 am

YWG

MDW

15h 35m

1 stop

$424Multiple Airlines

Mon, Aug 10 - Fri, Aug 14

3:20 pm - 12:55 am

MDW

YWG

9h 35m

1 stop

6:05 pm - 2:35 pm

YWG

MDW

20h 30m

1 stop

$435Multiple Airlines

Mon, Jul 20 - Tue, Jul 21

3:20 pm - 8:40 am

MDW

YWG

17h 20m

1 stop

5:10 pm - 9:40 am

YWG

MDW

16h 30m

1 stop

$452Multiple Airlines

Thu, Jul 9 - Tue, Jul 14

6:05 am - 10:10 pm

MDW

YWG

16h 05m

2 stops

6:05 pm - 9:40 am

YWG

MDW

15h 35m

1 stop

$482Multiple Airlines

Mon, Aug 10 - Fri, Aug 14

10:25 am - 7:25 pm

MDW

YWG

9h 00m

1 stop

8:10 pm - 2:35 pm

YWG

MDW

18h 25m

1 stop

$489Multiple Airlines

Wed, Jul 8 - Wed, Jul 15

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WestJet flights from Chicago Midway Airport to Winnipeg

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

WestJet

Sep 18

MDW10:48 amChicago Midway

9h 42m

2 stops

YWG8:30 pmWinnipeg

Sep 21

YWG6:15 amWinnipeg

10h 01m

2 stops

MDW4:16 pmChicago Midway

$683

WestJet

Jul 8

MDW1:18 pmChicago Midway

11h 37m

2 stops

YWG12:55 amWinnipeg

Jul 14

YWG6:15 amWinnipeg

12h 10m

2 stops

MDW6:25 pmChicago Midway

$808

WestJet

Jul 8

MDW9:54 amChicago Midway

5h 13m

1 stop

YWG3:07 pmWinnipeg

Jul 14

YWG12:46 pmWinnipeg

5h 32m

1 stop

MDW6:18 pmChicago Midway

$833

Delta flights from Chicago Midway Airport to Winnipeg

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

Delta

Jul 8

MDW6:00 amChicago Midway

9h 07m

2 stops

YWG3:07 pmWinnipeg

Jul 14

YWG6:40 amWinnipeg

11h 45m

2 stops

MDW6:25 pmChicago Midway

$1,087

Delta

Jul 5

MDW9:54 amChicago Midway

5h 10m

1 stop

YWG3:04 pmWinnipeg

Jul 12

YWG6:40 amWinnipeg

6h 29m

1 stop

MDW1:09 pmChicago Midway

$1,164

Delta

Jul 8

MDW6:00 amChicago Midway

9h 07m

2 stops

YWG3:07 pmWinnipeg

Jul 14

YWG6:40 amWinnipeg

11h 45m

2 stops

MDW6:25 pmChicago Midway

$1,179

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

Fri 7/17

3:20 pm-5:58 pm

2 stops26h 38m

Winnipeg

Fri 7/24

6:05 pm-9:40 am

1 stop15h 35m

$382

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 8/5

3:15 pm-9:45 am

1 stop18h 30m

Winnipeg

Sun 8/9

7:45 am-9:45 am

1 stop26h 00m

$389

Quickest round-trip

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 7/17

3:20 pm-12:55 am

1 stop9h 35m

Winnipeg

Fri 7/24

6:05 pm-9:40 am

1 stop15h 35m

$393

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 7/14

3:20 pm-8:40 am

1 stop17h 20m

Winnipeg

Sun 7/19

11:15 am-9:40 am

2 stops22h 25m

$398

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 7/14

10:25 am-8:40 am

1 stop22h 15m

Winnipeg

Sun 7/19

6:05 pm-9:40 am

1 stop15h 35m

$405

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 8/10

3:15 pm-9:45 am

1 stop18h 30m

Winnipeg

Fri 8/14

6:05 pm-9:40 am

1 stop15h 35m

$424

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 7/20

3:20 pm-12:55 am

1 stop9h 35m

Winnipeg

Tue 7/21

6:05 pm-2:35 pm

1 stop20h 30m

$435

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 7/9

3:20 pm-8:40 am

1 stop17h 20m

Winnipeg

Tue 7/14

5:10 pm-9:40 am

1 stop16h 30m

$452

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 8/10

6:05 am-10:10 pm

2 stops16h 05m

Winnipeg

Fri 8/14

6:05 pm-9:40 am

1 stop15h 35m

$482

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 7/8

10:25 am-7:25 pm

1 stop9h 00m

Winnipeg

Wed 7/15

8:10 pm-2:35 pm

1 stop18h 25m

$489

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 $585. 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 $1,062.

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

The cheapest time of day to fly to Winnipeg is at noon when flights can be purchased for as low as $556. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $809 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	5h 10m
Direct flights	None

The fastest flight from Chicago Midway Airport to Winnipeg takes 5h 10m

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 5h 10m 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.