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

Delta, WestJet, and Porter Airlines 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.

$201 Cheap Flights from Chicago Midway Airport to Winnipeg in 2025

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Find the cheapest flights from Chicago Midway Airport to Winnipeg

Round-trip

One-way

Last minute

Cheap round-trip flights

11:00 am - 7:35 pmMDW-YWG

8h 35m1 stop

8:20 pm - 10:05 amYWG-MDW

13h 45m1 stop

$376

Find Deal

Mon, Nov 10 - Fri, Nov 14

6:15 am - 4:23 pmMDW-YWG

10h 08m1 stop

9:05 pm - 2:01 pmYWG-MDW

16h 56m2 stops

$412

Find Deal

Fri, Aug 22 - Tue, Aug 26

11:00 am - 7:35 pmMDW-YWG

8h 35m1 stop

8:20 pm - 6:07 pmYWG-MDW

21h 47m2 stops

$429

Find Deal

Mon, Nov 10 - Fri, Nov 14

9:20 am - 4:50 pmMDW-YWG

7h 30m1 stop

8:35 am - 1:03 pmYWG-MDW

4h 28m1 stop

$440Delta

Find Deal

Wed, Sep 17 - Wed, Sep 24

9:31 am - 11:27 pmMDW-YWG

13h 56m2 stops

8:35 am - 1:03 pmYWG-MDW

4h 28m1 stop

$469Delta

Find Deal

Sat, Aug 23 - Tue, Aug 26

9:31 am - 11:27 pmMDW-YWG

13h 56m2 stops

6:40 am - 12:28 pmYWG-MDW

5h 48m2 stops

$475Delta

Find Deal

Sat, Aug 23 - Tue, Aug 26

12:43 pm - 4:23 pmMDW-YWG

27h 40m1 stop

9:05 pm - 9:36 amYWG-MDW

12h 31m2 stops

$553WestJet

Find Deal

Thu, Aug 21 - Mon, Aug 25

12:43 pm - 4:23 pmMDW-YWG

27h 40m1 stop

6:30 am - 9:44 pmYWG-MDW

15h 14m2 stops

$560WestJet

Find Deal

Thu, Aug 21 - Tue, Aug 26

4:15 pm - 11:13 amMDW-YWG

18h 58m2 stops

4:25 pm - 10:05 amYWG-MDW

17h 40m2 stops

$620Porter Airlines

Find Deal

Fri, Oct 31 - Wed, Nov 5

4:15 pm - 11:13 amMDW-YWG

18h 58m2 stops

4:25 pm - 10:05 amYWG-MDW

17h 40m2 stops

$622Porter Airlines

Find Deal

Fri, Oct 31 - Wed, Nov 5

Porter Airlines flights from Chicago Midway Airport to Winnipeg

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

Porter Airlines

Oct 31

MDW4:15 pmChicago Midway

18h 58m

2 stops

YWG11:13 amWinnipeg

Nov 5

YWG4:25 pmWinnipeg

17h 40m

2 stops

MDW10:05 amChicago Midway

$620

Find similar

Porter Airlines

Oct 31

MDW4:15 pmChicago Midway

18h 58m

2 stops

YWG11:13 amWinnipeg

Nov 5

YWG4:25 pmWinnipeg

17h 40m

2 stops

MDW10:05 amChicago Midway

$622

Find similar

Porter Airlines

Aug 17

MDW9:40 amChicago Midway

13h 06m

2 stops

YWG10:46 pmWinnipeg

Aug 31

YWG6:10 amWinnipeg

10h 14m

1 stop

MDW4:24 pmChicago Midway

$643

Find similar

WestJet flights from Chicago Midway Airport to Winnipeg

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

WestJet

Aug 21

MDW12:43 pmChicago Midway

27h 40m

1 stop

YWG4:23 pmWinnipeg

Aug 25

YWG9:05 pmWinnipeg

12h 31m

2 stops

MDW9:36 amChicago Midway

$553

Find similar

WestJet

Aug 21

MDW12:43 pmChicago Midway

27h 40m

1 stop

YWG4:23 pmWinnipeg

Aug 26

YWG6:30 amWinnipeg

15h 14m

2 stops

MDW9:44 pmChicago Midway

$560

Find similar

WestJet

Sep 17

MDW9:20 amChicago Midway

14h 53m

2 stops

YWG12:13 amWinnipeg

Sep 24

YWG2:35 pmWinnipeg

27h 00m

2 stops

MDW5:35 pmChicago Midway

$562

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

Mon 11/10

11:00 am-7:35 pm

1 stop8h 35m

Winnipeg

Fri 11/14

8:20 pm-10:05 am

1 stop13h 45m

$376

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 8/22

6:15 am-4:23 pm

1 stop10h 08m

Winnipeg

Tue 8/26

9:05 pm-2:01 pm

2 stops16h 56m

$412

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 11/10

11:00 am-7:35 pm

1 stop8h 35m

Winnipeg

Fri 11/14

8:20 pm-6:07 pm

2 stops21h 47m

$429

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 9/17

9:20 am-4:50 pm

1 stop7h 30m

Winnipeg

Wed 9/24

8:35 am-1:03 pm

1 stop4h 28m

$440

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 8/23

9:31 am-11:27 pm

2 stops13h 56m

Winnipeg

Tue 8/26

8:35 am-1:03 pm

1 stop4h 28m

$469

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 8/23

9:31 am-11:27 pm

2 stops13h 56m

Winnipeg

Tue 8/26

6:40 am-12:28 pm

2 stops5h 48m

$475

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 8/21

12:43 pm-4:23 pm

1 stop27h 40m

Winnipeg

Mon 8/25

9:05 pm-9:36 am

2 stops12h 31m

$553

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 8/21

12:43 pm-4:23 pm

1 stop27h 40m

Winnipeg

Tue 8/26

6:30 am-9:44 pm

2 stops15h 14m

$560

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 10/31

4:15 pm-11:13 am

2 stops18h 58m

Winnipeg

Wed 11/5

4:25 pm-10:05 am

2 stops17h 40m

$620

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 10/31

4:15 pm-11:13 am

2 stops18h 58m

Winnipeg

Wed 11/5

4:25 pm-10:05 am

2 stops17h 40m

$622

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 Friday when prices can be found for as low as $543. 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 $737.

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 $635 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

Best Price Found	$201
Fastest flight time	4h 10m
Direct flights	None
Airports in Winnipeg	1 airport

The best one-way flight to Winnipeg from Chicago Midway Airport in the past 72 hours is $201. The best round-trip flight deal from Chicago Midway Airport to Winnipeg found on momondo in the last 72 hours is $376.

The fastest flight from Chicago Midway Airport to Winnipeg takes 4h 10m

There are no direct flights from Chicago Midway Airport to Winnipeg. Popular non-direct route for this connection is Chicago Midway Airport - Winnipeg Airport.

There is 1 airport near Winnipeg: Winnipeg (YWG)

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 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.

Scanterbury

Selkirk

Morden

Portage la Prairie

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.