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

WestJet 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.

$210 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.

11:45 am - 8:45 pmMDW Chicago Midway-YWG Winnipeg

9h 00m1 stop Toronto Island

11:15 am - 11:00 amYWG Winnipeg-MDW Chicago Midway

23h 45m2 stops Montreal St Hubert Toronto Pearson Intl

$327Multiple Airlines

Thu, Sep 10 - Sun, Sep 13

3:20 pm - 12:55 amMDW Chicago Midway-YWG Winnipeg

9h 35m1 stop Toronto Island

11:15 am - 11:00 amYWG Winnipeg-MDW Chicago Midway

23h 45m2 stops Montreal St Hubert Toronto Island

$330Multiple Airlines

Thu, Sep 10 - Sun, Sep 13

3:20 pm - 12:55 amMDW Chicago Midway-YWG Winnipeg

9h 35m1 stop Toronto Island

11:15 am - 11:00 amYWG Winnipeg-MDW Chicago Midway

23h 45m2 stops Montreal St Hubert Toronto Island

$341Multiple Airlines

Fri, Sep 11 - Sun, Sep 13

3:20 pm - 12:55 amMDW Chicago Midway-YWG Winnipeg

9h 35m1 stop Toronto Island

7:45 am - 11:00 amYWG Winnipeg-MDW Chicago Midway

27h 15m1 stop Toronto Pearson Intl

$345Multiple Airlines

Fri, Sep 11 - Sun, Sep 13

3:20 pm - 12:55 amMDW Chicago Midway-YWG Winnipeg

9h 35m1 stop Toronto Island

11:15 am - 11:00 amYWG Winnipeg-MDW Chicago Midway

23h 45m2 stops Montreal St Hubert Toronto Island

$349Multiple Airlines

Fri, Sep 11 - Sun, Sep 13

3:20 pm - 12:55 amMDW Chicago Midway-YWG Winnipeg

9h 35m1 stop Toronto Island

6:05 pm - 11:00 amYWG Winnipeg-MDW Chicago Midway

16h 55m1 stop Toronto Pearson Intl

$350Multiple Airlines

Fri, Sep 11 - Sun, Sep 13

11:45 am - 7:49 pmMDW Chicago Midway-YWG Winnipeg

8h 04m1 stop Toronto Island

8:45 pm - 11:00 amYWG Winnipeg-MDW Chicago Midway

14h 15m1 stop Toronto Pearson Intl

$379Porter Airlines

Thu, Sep 10 - Sun, Sep 13

11:45 am - 7:49 pmMDW Chicago Midway-YWG Winnipeg

8h 04m1 stop Toronto Island

8:45 pm - 11:00 amYWG Winnipeg-MDW Chicago Midway

14h 15m1 stop Toronto Pearson Intl

$390Porter Airlines

Thu, Sep 10 - Sun, Sep 13

10:20 am - 8:40 amMDW Chicago Midway-YWG Winnipeg

22h 20m1 stop Toronto Island

12:15 pm - 2:35 pmYWG Winnipeg-MDW Chicago Midway

26h 20m1 stop Toronto Pearson Intl

$499Multiple Airlines

Sat, Aug 29 - Tue, Sep 1

3:15 pm - 8:40 amMDW Chicago Midway-YWG Winnipeg

17h 25m1 stop Toronto Island

6:05 pm - 2:35 pmYWG Winnipeg-MDW Chicago Midway

20h 30m1 stop Toronto Pearson Intl

$500Multiple Airlines

Tue, Aug 25 - Tue, Sep 1

Cheap last minute flights

Enter your travel dates to find the best prices.

9:24 am - 8:30 pmMDW Chicago Midway-YWG Winnipeg

11h 06m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl

12:46 pm - 6:01 pmYWG Winnipeg-MDW Chicago Midway

5h 15m1 stop Minneapolis St Paul

$1,098WestJet

Fri, Aug 14 - Sat, Aug 15

7:25 pm - 11:30 pmMDW Chicago Midway-YWG Winnipeg

4h 05m1 stop Minneapolis St Paul

11:15 am - 9:45 amYWG Winnipeg-MDW Chicago Midway

22h 30m2 stops Montreal St Hubert Toronto Island

$1,102Multiple Airlines

Mon, Aug 17 - Wed, Aug 19

7:25 pm - 11:30 pmMDW Chicago Midway-YWG Winnipeg

4h 05m1 stop Minneapolis St Paul

6:40 am - 6:01 pmYWG Winnipeg-MDW Chicago Midway

11h 21m1 stop Minneapolis St Paul

$1,170WestJet

Fri, Aug 14 - Sun, Aug 16

1:25 pm - 12:55 amMDW Chicago Midway-YWG Winnipeg

11h 30m2 stops Detroit Metropolitan Wayne County Calgary

6:15 am - 10:36 pmYWG Winnipeg-MDW Chicago Midway

40h 21m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson

$1,261WestJet

Fri, Aug 14 - Sun, Aug 16

7:25 pm - 11:54 amMDW Chicago Midway-YWG Winnipeg

16h 29m1 stop Minneapolis St Paul

6:15 am - 10:36 pmYWG Winnipeg-MDW Chicago Midway

40h 21m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson

$1,265WestJet

Fri, Aug 14 - Sun, Aug 16

1:25 pm - 12:55 amMDW Chicago Midway-YWG Winnipeg

11h 30m2 stops Detroit Metropolitan Wayne County Calgary

6:15 am - 4:15 pmYWG Winnipeg-MDW Chicago Midway

34h 00m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson

$1,266WestJet

Mon, Aug 17 - Wed, Aug 19

9:24 am - 8:30 pmMDW Chicago Midway-YWG Winnipeg

11h 06m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl

7:00 am - 6:01 pmYWG Winnipeg-MDW Chicago Midway

11h 01m2 stops Edmonton Minneapolis St Paul

$1,323WestJet

Fri, Aug 14 - Sat, Aug 15

7:25 pm - 11:54 amMDW Chicago Midway-YWG Winnipeg

16h 29m1 stop Minneapolis St Paul

12:46 pm - 6:01 pmYWG Winnipeg-MDW Chicago Midway

5h 15m1 stop Minneapolis St Paul

$1,334WestJet

Mon, Aug 17 - Wed, Aug 19

7:25 pm - 11:30 pmMDW Chicago Midway-YWG Winnipeg

4h 05m1 stop Minneapolis St Paul

5:42 pm - 6:01 pmYWG Winnipeg-MDW Chicago Midway

24h 19m1 stop Minneapolis St Paul

$1,336WestJet

Fri, Aug 14 - Sat, Aug 15

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Porter Airlines flights from Chicago Midway Airport to Winnipeg

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

Porter Airlines

Sep 10

MDW11:45 amChicago Midway

8h 04m

1 stop

YWG7:49 pmWinnipeg

Sep 13

YWG8:45 pmWinnipeg

14h 15m

1 stop

MDW11:00 amChicago Midway

$379

Porter Airlines

Sep 10

MDW11:45 amChicago Midway

8h 04m

1 stop

YWG7:49 pmWinnipeg

Sep 13

YWG8:45 pmWinnipeg

14h 15m

1 stop

MDW11:00 amChicago Midway

$390

Porter Airlines

Aug 25

MDW3:15 pmChicago Midway

28h 39m

1 stop

YWG7:54 pmWinnipeg

Sep 1

YWG11:15 amWinnipeg

27h 20m

2 stops

MDW2:35 pmChicago Midway

$510

WestJet flights from Chicago Midway Airport to Winnipeg

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

WestJet

Sep 23

MDW9:59 amChicago Midway

6h 55m

1 stop

YWG4:54 pmWinnipeg

Sep 30

YWG12:41 pmWinnipeg

5h 38m

1 stop

MDW6:19 pmChicago Midway

$652

WestJet

Sep 30

MDW10:48 amChicago Midway

9h 32m

2 stops

YWG8:20 pmWinnipeg

Oct 5

YWG7:45 amWinnipeg

10h 48m

2 stops

MDW6:33 pmChicago Midway

$659

WestJet

Oct 1

MDW9:29 amChicago Midway

11h 16m

2 stops

YWG8:45 pmWinnipeg

Oct 10

YWG6:15 amWinnipeg

11h 45m

2 stops

MDW6:00 pmChicago Midway

$676

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 Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Thu 9/10

11:45 am-8:45 pm

1 stop9h 00m

Winnipeg

Sun 9/13

11:15 am-11:00 am

2 stops23h 45m

$327

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Thu 9/10

3:20 pm-12:55 am

1 stop9h 35m

Winnipeg

Sun 9/13

11:15 am-11:00 am

2 stops23h 45m

$330

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Fri 9/11

3:20 pm-12:55 am

1 stop9h 35m

Winnipeg

Sun 9/13

11:15 am-11:00 am

2 stops23h 45m

$341

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Fri 9/11

3:20 pm-12:55 am

1 stop9h 35m

Winnipeg

Sun 9/13

7:45 am-11:00 am

1 stop27h 15m

$345

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Fri 9/11

3:20 pm-12:55 am

1 stop9h 35m

Winnipeg

Sun 9/13

11:15 am-11:00 am

2 stops23h 45m

$349

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Fri 9/11

3:20 pm-12:55 am

1 stop9h 35m

Winnipeg

Sun 9/13

6:05 pm-11:00 am

1 stop16h 55m

$350

Quickest round-trip

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Thu 9/10

11:45 am-7:49 pm

1 stop8h 04m

Winnipeg

Sun 9/13

8:45 pm-11:00 am

1 stop14h 15m

$379

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Thu 9/10

11:45 am-7:49 pm

1 stop8h 04m

Winnipeg

Sun 9/13

8:45 pm-11:00 am

1 stop14h 15m

$390

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Sat 8/29

10:20 am-8:40 am

1 stop22h 20m

Winnipeg

Tue 9/1

12:15 pm-2:35 pm

1 stop26h 20m

$499

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Tue 8/25

3:15 pm-8:40 am

1 stop17h 25m

Winnipeg

Tue 9/1

6:05 pm-2:35 pm

1 stop20h 30m

$500

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 $699. 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 $1,150.

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 $493. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $878 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	7h 26m
Direct flights	None

The fastest flight from Chicago Midway Airport to Winnipeg takes 7h 26m

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

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 7h 26m 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.