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.

$208 Cheap Flights from Chicago Midway Airport to Winnipeg in 2026/27

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.

6:42 pm - 5:25 pmMDW Chicago Midway-YWG Winnipeg

22h 43m2 stops Atlanta Hartsfield-Jackson Calgary

8:35 pm - 5:47 pmYWG Winnipeg-MDW Chicago Midway

21h 12m2 stops Calgary Atlanta Hartsfield-Jackson

$451Multiple Airlines

Thu, Oct 29 - Sun, Nov 1

6:16 am - 12:10 amMDW Chicago Midway-YWG Winnipeg

17h 54m2 stops Atlanta Hartsfield-Jackson Calgary

8:35 pm - 5:47 pmYWG Winnipeg-MDW Chicago Midway

21h 12m2 stops Calgary Atlanta Hartsfield-Jackson

$460Multiple Airlines

Mon, Nov 9 - Wed, Nov 11

11:45 am - 12:55 amMDW Chicago Midway-YWG Winnipeg

13h 10m1 stop Toronto Island

9:35 pm - 5:47 pmYWG Winnipeg-MDW Chicago Midway

20h 12m2 stops Calgary Atlanta Hartsfield-Jackson

$469Multiple Airlines

Wed, Oct 21 - Wed, Oct 28

3:20 pm - 8:30 pmMDW Chicago Midway-YWG Winnipeg

29h 10m1 stop Toronto Island

9:35 pm - 5:47 pmYWG Winnipeg-MDW Chicago Midway

20h 12m2 stops Calgary Atlanta Hartsfield-Jackson

$477Multiple Airlines

Thu, Oct 22 - Tue, Oct 27

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

9h 35m1 stop Toronto Island

9:35 pm - 5:47 pmYWG Winnipeg-MDW Chicago Midway

20h 12m2 stops Calgary Atlanta Hartsfield-Jackson

$484Multiple Airlines

Tue, Oct 20 - Tue, Oct 27

6:42 pm - 5:25 pmMDW Chicago Midway-YWG Winnipeg

22h 43m2 stops Atlanta Hartsfield-Jackson Calgary

8:35 pm - 5:47 pmYWG Winnipeg-MDW Chicago Midway

21h 12m2 stops Calgary Atlanta Hartsfield-Jackson

$490Multiple Airlines

Fri, Oct 30 - Sun, Nov 1

1:18 pm - 4:25 pmMDW Chicago Midway-YWG Winnipeg

27h 07m2 stops Atlanta Hartsfield-Jackson Calgary

7:00 am - 11:46 pmYWG Winnipeg-MDW Chicago Midway

16h 46m1 stop Atlanta Hartsfield-Jackson

$491Multiple Airlines

Sat, Jan 9 - Wed, Jan 13

1:18 pm - 2:40 pmMDW Chicago Midway-YWG Winnipeg

25h 22m1 stop Atlanta Hartsfield-Jackson

7:00 am - 11:46 pmYWG Winnipeg-MDW Chicago Midway

16h 46m1 stop Atlanta Hartsfield-Jackson

$494Multiple Airlines

Sun, Jan 10 - Wed, Jan 13

12:27 pm - 5:25 pmMDW Chicago Midway-YWG Winnipeg

28h 58m3 stops Dallas/Fort Worth Atlanta Hartsfield-Jackson Calgary

8:35 pm - 5:47 pmYWG Winnipeg-MDW Chicago Midway

21h 12m2 stops Calgary Atlanta Hartsfield-Jackson

$494Multiple Airlines

Tue, Oct 27 - Tue, Nov 3

6:42 pm - 10:55 pmMDW Chicago Midway-YWG Winnipeg

28h 13m2 stops Atlanta Hartsfield-Jackson Calgary

8:35 pm - 5:47 pmYWG Winnipeg-MDW Chicago Midway

21h 12m2 stops Calgary Atlanta Hartsfield-Jackson

$497Multiple Airlines

Tue, Oct 27 - Tue, Nov 3

Cheap last minute flights

Enter your travel dates to find the best prices.

3:20 pm - 8:40 amMDW Chicago Midway-YWG Winnipeg

17h 20m1 stop Toronto Island

7:55 pm - 11:00 amYWG Winnipeg-MDW Chicago Midway

15h 05m1 stop Toronto Pearson Intl

$771Multiple Airlines

Thu, Oct 1 - Fri, Oct 2

3:20 pm - 8:40 amMDW Chicago Midway-YWG Winnipeg

17h 20m1 stop Toronto Island

9:05 pm - 2:35 pmYWG Winnipeg-MDW Chicago Midway

17h 30m2 stops Calgary Toronto Pearson Intl

$780Multiple Airlines

Thu, Oct 1 - Fri, Oct 2

3:20 pm - 8:40 amMDW Chicago Midway-YWG Winnipeg

17h 20m1 stop Toronto Island

5:10 pm - 11:00 amYWG Winnipeg-MDW Chicago Midway

17h 50m1 stop Toronto Pearson Intl

$788Multiple Airlines

Thu, Oct 1 - Sat, Oct 3

3:20 pm - 8:40 amMDW Chicago Midway-YWG Winnipeg

17h 20m1 stop Toronto Island

7:10 pm - 2:35 pmYWG Winnipeg-MDW Chicago Midway

19h 25m2 stops Calgary Toronto Pearson Intl

$804Multiple Airlines

Thu, Oct 1 - Sat, Oct 3

3:20 pm - 12:15 pmMDW Chicago Midway-YWG Winnipeg

20h 55m2 stops Toronto Island Calgary

9:05 pm - 2:35 pmYWG Winnipeg-MDW Chicago Midway

17h 30m2 stops Calgary Toronto Pearson Intl

$1,064Multiple Airlines

Thu, Oct 1 - Fri, Oct 2

3:20 pm - 12:15 pmMDW Chicago Midway-YWG Winnipeg

20h 55m2 stops Toronto Island Calgary

4:05 pm - 2:35 pmYWG Winnipeg-MDW Chicago Midway

22h 30m3 stops Halifax Intl Ottawa Toronto Island

$1,098Multiple Airlines

Thu, Oct 1 - Sat, Oct 3

3:20 pm - 12:15 pmMDW Chicago Midway-YWG Winnipeg

20h 55m2 stops Toronto Island Calgary

7:10 pm - 2:35 pmYWG Winnipeg-MDW Chicago Midway

19h 25m2 stops Calgary Toronto Pearson Intl

$1,099Multiple Airlines

Thu, Oct 1 - Sat, Oct 3

3:20 pm - 5:58 pmMDW Chicago Midway-YWG Winnipeg

26h 38m2 stops Toronto Island Ottawa

12:41 pm - 6:19 pmYWG Winnipeg-MDW Chicago Midway

5h 38m1 stop Minneapolis St Paul

$1,101Multiple Airlines

Thu, Oct 1 - Sun, Oct 4

11:45 am - 5:58 pmMDW Chicago Midway-YWG Winnipeg

30h 13m2 stops Toronto Island Ottawa

11:15 am - 2:35 pmYWG Winnipeg-MDW Chicago Midway

27h 20m2 stops MET - Montreal Metropolitan Toronto Island

$1,124Porter Airlines

Fri, Oct 2 - Tue, Oct 6

3:20 pm - 5:58 pmMDW Chicago Midway-YWG Winnipeg

26h 38m2 stops Toronto Island Ottawa

4:15 pm - 11:00 amYWG Winnipeg-MDW Chicago Midway

18h 45m2 stops Ottawa Toronto Island

$1,126Porter Airlines

Thu, Oct 1 - Mon, Oct 5

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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

Oct 27

MDW12:27 pmChicago Midway

12h 17m

2 stops

YWG12:44 amWinnipeg

Nov 10

YWG5:00 amWinnipeg

13h 04m

2 stops

MDW6:04 pmChicago Midway

$845

WestJet

Oct 27

MDW10:12 amChicago Midway

14h 32m

2 stops

YWG12:44 amWinnipeg

Nov 3

YWG5:00 amWinnipeg

13h 00m

2 stops

MDW6:00 pmChicago Midway

$846

WestJet

Nov 4

MDW9:29 amChicago Midway

15h 15m

2 stops

YWG12:44 amWinnipeg

Nov 11

YWG5:00 amWinnipeg

11h 18m

2 stops

MDW4:18 pmChicago Midway

$850

Delta flights from Chicago Midway Airport to Winnipeg

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

Delta

Jan 9

MDW1:00 pmChicago Midway

22h 50m

2 stops

YWG11:50 amWinnipeg

Jan 13

YWG6:35 amWinnipeg

12h 02m

2 stops

MDW6:37 pmChicago Midway

$679

Delta

Jan 9

MDW5:35 pmChicago Midway

5h 59m

1 stop

YWG11:34 pmWinnipeg

Jan 14

YWG12:30 pmWinnipeg

4h 20m

1 stop

MDW4:50 pmChicago Midway

$808

Delta

Nov 4

MDW1:27 pmChicago Midway

9h 52m

2 stops

YWG11:19 pmWinnipeg

Nov 13

YWG6:35 amWinnipeg

5h 15m

1 stop

MDW11:50 amChicago Midway

$810

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 10/29

6:42 pm-5:25 pm

2 stops22h 43m

Winnipeg

Sun 11/1

8:35 pm-5:47 pm

2 stops21h 12m

$451

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Mon 11/9

6:16 am-12:10 am

2 stops17h 54m

Winnipeg

Wed 11/11

8:35 pm-5:47 pm

2 stops21h 12m

$460

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Wed 10/21

11:45 am-12:55 am

1 stop13h 10m

Winnipeg

Wed 10/28

9:35 pm-5:47 pm

2 stops20h 12m

$469

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Thu 10/22

3:20 pm-8:30 pm

1 stop29h 10m

Winnipeg

Tue 10/27

9:35 pm-5:47 pm

2 stops20h 12m

$477

Quickest round-trip

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Tue 10/20

3:20 pm-12:55 am

1 stop9h 35m

Winnipeg

Tue 10/27

9:35 pm-5:47 pm

2 stops20h 12m

$484

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Fri 10/30

6:42 pm-5:25 pm

2 stops22h 43m

Winnipeg

Sun 11/1

8:35 pm-5:47 pm

2 stops21h 12m

$490

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Sat 1/9

1:18 pm-4:25 pm

2 stops27h 07m

Winnipeg

Wed 1/13

7:00 am-11:46 pm

1 stop16h 46m

$491

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Sun 1/10

1:18 pm-2:40 pm

1 stop25h 22m

Winnipeg

Wed 1/13

7:00 am-11:46 pm

1 stop16h 46m

$494

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Tue 10/27

12:27 pm-5:25 pm

3 stops28h 58m

Winnipeg

Tue 11/3

8:35 pm-5:47 pm

2 stops21h 12m

$494

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Tue 10/27

6:42 pm-10:55 pm

2 stops28h 13m

Winnipeg

Tue 11/3

8:35 pm-5:47 pm

2 stops21h 12m

$497

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 Saturday when prices can be found for as low as $755. 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 $1,315.

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 $844. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $920 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

Best Price Found	$208
Fastest flight time	4h 30m
Direct flights	None

The best one-way flight to Winnipeg from Chicago Midway Airport in the past 72 hours is $208. The best round-trip flight deal from Chicago Midway Airport to Winnipeg found on momondo in the last 72 hours is $451.

The fastest flight from Chicago Midway Airport to Winnipeg takes 4h 30m

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 4h 30m 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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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.