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.

$115 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

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:30 am - 12:40 am

MDW

YWG

17h 10m2 stops

7:30 am - 7:07 pm

YWG

MDW

11h 37m1 stop

$246Multiple Airlines

Tue, Mar 3 - Wed, Mar 4

12:57 pm - 12:43 am

MDW

YWG

11h 46m1 stop

9:00 pm - 12:05 pm

YWG

MDW

15h 05m2 stops

$260Multiple Airlines

Mon, Jan 19 - Mon, Jan 26

1:00 pm - 5:26 pm

MDW

YWG

28h 26m1 stop

4:25 pm - 10:10 am

YWG

MDW

17h 45m2 stops

$356Multiple Airlines

Mon, Feb 2 - Mon, Feb 9

11:00 am - 12:39 am

MDW

YWG

13h 39m1 stop

7:30 am - 7:07 pm

YWG

MDW

11h 37m1 stop

$383Multiple Airlines

Tue, Mar 3 - Wed, Mar 4

11:05 am - 11:13 am

MDW

YWG

24h 08m2 stops

5:21 pm - 6:36 pm

YWG

MDW

25h 15m1 stop

$427Multiple Airlines

Tue, Feb 3 - Tue, Feb 10

9:50 am - 11:03 am

MDW

YWG

25h 13m1 stop

12:20 pm - 9:09 am

YWG

MDW

20h 49m2 stops

$445Multiple Airlines

Thu, Jan 8 - Thu, Jan 15

9:50 am - 7:09 pm

MDW

YWG

9h 19m2 stops

5:00 am - 5:37 pm

YWG

MDW

12h 37m2 stops

$476WestJet

Thu, Feb 26 - Sun, Mar 1

1:51 pm - 11:03 am

MDW

YWG

21h 12m1 stop

5:21 pm - 6:36 pm

YWG

MDW

25h 15m1 stop

$488WestJet

Tue, Feb 3 - Tue, Feb 10

1:49 pm - 11:03 am

MDW

YWG

21h 14m1 stop

12:20 pm - 8:52 am

YWG

MDW

20h 32m2 stops

$500WestJet

Thu, Jan 8 - Thu, Jan 15

9:50 am - 11:01 am

MDW

YWG

25h 11m1 stop

8:05 pm - 12:46 pm

YWG

MDW

16h 41m2 stops

$541WestJet

Thu, Feb 26 - Sun, Mar 1

WestJet flights from Chicago Midway Airport to Winnipeg

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

WestJet

Feb 26

MDW9:50 amChicago Midway

9h 19m

2 stops

YWG7:09 pmWinnipeg

Mar 1

YWG5:00 amWinnipeg

12h 37m

2 stops

MDW5:37 pmChicago Midway

$476

Find similar

WestJet

Feb 3

MDW1:51 pmChicago Midway

21h 12m

1 stop

YWG11:03 amWinnipeg

Feb 10

YWG5:21 pmWinnipeg

25h 15m

1 stop

MDW6:36 pmChicago Midway

$488

Find similar

WestJet

Jan 8

MDW1:49 pmChicago Midway

21h 14m

1 stop

YWG11:03 amWinnipeg

Jan 15

YWG12:20 pmWinnipeg

20h 32m

2 stops

MDW8:52 amChicago Midway

$500

Find similar

Delta flights from Chicago Midway Airport to Winnipeg

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

Delta

Feb 2

MDW7:16 pmChicago Midway

4h 22m

1 stop

YWG11:38 pmWinnipeg

Feb 9

YWG11:53 amWinnipeg

6h 43m

1 stop

MDW6:36 pmChicago Midway

$654

Find similar

Delta

Jun 5

MDW6:45 pmChicago Midway

4h 42m

1 stop

YWG11:27 pmWinnipeg

Jun 7

YWG8:50 amWinnipeg

4h 17m

1 stop

MDW1:07 pmChicago Midway

$772

Find similar

Delta

Jan 19

MDW7:16 pmChicago Midway

4h 22m

1 stop

YWG11:38 pmWinnipeg

Jan 26

YWG11:53 amWinnipeg

6h 43m

1 stop

MDW6:36 pmChicago Midway

$804

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 3/3

7:30 am-12:40 am

2 stops17h 10m

Winnipeg

Wed 3/4

7:30 am-7:07 pm

1 stop11h 37m

$246

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 1/19

12:57 pm-12:43 am

1 stop11h 46m

Winnipeg

Mon 1/26

9:00 pm-12:05 pm

2 stops15h 05m

$260

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 2/2

1:00 pm-5:26 pm

1 stop28h 26m

Winnipeg

Mon 2/9

4:25 pm-10:10 am

2 stops17h 45m

$356

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 3/3

11:00 am-12:39 am

1 stop13h 39m

Winnipeg

Wed 3/4

7:30 am-7:07 pm

1 stop11h 37m

$383

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 2/3

11:05 am-11:13 am

2 stops24h 08m

Winnipeg

Tue 2/10

5:21 pm-6:36 pm

1 stop25h 15m

$427

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 1/8

9:50 am-11:03 am

1 stop25h 13m

Winnipeg

Thu 1/15

12:20 pm-9:09 am

2 stops20h 49m

$445

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 2/26

9:50 am-7:09 pm

2 stops9h 19m

Winnipeg

Sun 3/1

5:00 am-5:37 pm

2 stops12h 37m

$476

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 2/3

1:51 pm-11:03 am

1 stop21h 12m

Winnipeg

Tue 2/10

5:21 pm-6:36 pm

1 stop25h 15m

$488

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 1/8

1:49 pm-11:03 am

1 stop21h 14m

Winnipeg

Thu 1/15

12:20 pm-8:52 am

2 stops20h 32m

$500

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 2/26

9:50 am-11:01 am

1 stop25h 11m

Winnipeg

Sun 3/1

8:05 pm-12:46 pm

2 stops16h 41m

$541

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 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, 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 $648.

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

Fastest flight time	5h 07m
Direct flights	None

The fastest flight from Chicago Midway Airport to Winnipeg takes 5h 07m

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 5h 07m 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

Selkirk

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.