When did momondo last update prices for flights from Winnipeg Airport to Chicago Midway Airport?

Prices for flights from Winnipeg Airport to Chicago Midway Airport are updated daily.

How old do you have to be to fly from Winnipeg Airport to Chicago Midway Airport?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Chicago Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$156 Cheap Flights from Winnipeg to Chicago Midway Airport in 2026

1 adult

0 bags

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Find the cheapest flights from Winnipeg to Chicago

Round-trip

One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

7:30 am - 7:31 pm

YWG

MDW

12h 01m

1 stop

11:00 am - 11:13 am

MDW

YWG

24h 13m

2 stops

$428Multiple Airlines

Fri, Apr 24 - Tue, Apr 28

8:20 pm - 12:10 pm

YWG

MDW

15h 50m

1 stop

4:05 pm - 3:30 pm

MDW

YWG

23h 25m

1 stop

$474Multiple Airlines

Fri, Apr 10 - Sun, Apr 12

8:20 pm - 12:10 pm

YWG

MDW

15h 50m

1 stop

4:05 pm - 11:13 am

MDW

YWG

19h 08m

2 stops

$487Multiple Airlines

Fri, Apr 10 - Sun, Apr 12

11:55 am - 1:32 pm

YWG

MDW

25h 37m

1 stop

2:12 pm - 10:56 am

MDW

YWG

20h 44m

1 stop

$492WestJet

Fri, Apr 24 - Tue, Apr 28

8:10 pm - 12:10 pm

YWG

MDW

16h 00m

1 stop

4:05 pm - 8:40 am

MDW

YWG

16h 35m

1 stop

$501Multiple Airlines

Fri, Apr 17 - Sun, Apr 19

12:20 pm - 8:53 am

YWG

MDW

20h 33m

2 stops

7:16 pm - 10:56 am

MDW

YWG

15h 40m

1 stop

$502WestJet

Sat, Apr 11 - Sat, Apr 25

6:40 am - 6:36 pm

YWG

MDW

11h 56m

1 stop

7:16 pm - 10:56 am

MDW

YWG

15h 40m

1 stop

$504WestJet

Sat, Apr 18 - Mon, Apr 20

5:20 pm - 1:32 pm

YWG

MDW

20h 12m

1 stop

1:24 pm - 12:55 am

MDW

YWG

11h 31m

2 stops

$511WestJet

Fri, Apr 24 - Mon, Apr 27

5:20 pm - 1:32 pm

YWG

MDW

20h 12m

1 stop

7:16 pm - 10:56 am

MDW

YWG

15h 40m

1 stop

$514WestJet

Fri, Apr 24 - Mon, Apr 27

11:55 am - 6:36 pm

YWG

MDW

6h 41m

1 stop

9:29 am - 10:56 am

MDW

YWG

25h 27m

1 stop

$515WestJet

Sat, Apr 18 - Mon, Apr 20

WestJet flights from Winnipeg to Chicago Midway Airport

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

WestJet

Apr 24

YWG11:55 amWinnipeg

25h 37m

1 stop

MDW1:32 pmChicago Midway

Apr 28

MDW2:12 pmChicago Midway

20h 44m

1 stop

YWG10:56 amWinnipeg

$492

WestJet

Apr 11

YWG12:20 pmWinnipeg

20h 33m

2 stops

MDW8:53 amChicago Midway

Apr 25

MDW7:16 pmChicago Midway

15h 40m

1 stop

YWG10:56 amWinnipeg

$502

WestJet

Apr 18

YWG6:40 amWinnipeg

11h 56m

1 stop

MDW6:36 pmChicago Midway

Apr 20

MDW7:16 pmChicago Midway

15h 40m

1 stop

YWG10:56 amWinnipeg

$504

momondo Fare Finder

Use the filters below to find and compare flights from Winnipeg to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 4/24

7:30 am-7:31 pm

1 stop12h 01m

Chicago Midway

Tue 4/28

11:00 am-11:13 am

2 stops24h 13m

$428

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 4/10

8:20 pm-12:10 pm

1 stop15h 50m

Chicago Midway

Sun 4/12

4:05 pm-3:30 pm

1 stop23h 25m

$474

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 4/10

8:20 pm-12:10 pm

1 stop15h 50m

Chicago Midway

Sun 4/12

4:05 pm-11:13 am

2 stops19h 08m

$487

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 4/24

11:55 am-1:32 pm

1 stop25h 37m

Chicago Midway

Tue 4/28

2:12 pm-10:56 am

1 stop20h 44m

$492

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 4/17

8:10 pm-12:10 pm

1 stop16h 00m

Chicago Midway

Sun 4/19

4:05 pm-8:40 am

1 stop16h 35m

$501

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 4/11

12:20 pm-8:53 am

2 stops20h 33m

Chicago Midway

Sat 4/25

7:16 pm-10:56 am

1 stop15h 40m

$502

Quickest round-trip

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 4/18

6:40 am-6:36 pm

1 stop11h 56m

Chicago Midway

Mon 4/20

7:16 pm-10:56 am

1 stop15h 40m

$504

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 4/24

5:20 pm-1:32 pm

1 stop20h 12m

Chicago Midway

Mon 4/27

1:24 pm-12:55 am

2 stops11h 31m

$511

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 4/24

5:20 pm-1:32 pm

1 stop20h 12m

Chicago Midway

Mon 4/27

7:16 pm-10:56 am

1 stop15h 40m

$514

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 4/18

11:55 am-6:36 pm

1 stop6h 41m

Chicago Midway

Mon 4/20

9:29 am-10:56 am

1 stop25h 27m

$515

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 Winnipeg to Chicago Midway Airport

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

Can stopping save me money on Winnipeg to Chicago Midway Airport flights?

You could potentially save up to 19% on your flight if you consider stops on a Winnipeg to Chicago Midway Airport flight.

When to book flights from Winnipeg to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Winnipeg to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Winnipeg to Chicago Midway Airport (YWG to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Chicago Midway Airport

Fastest flight time	5h 25m
Direct flights	None

The fastest flight from Winnipeg to Chicago Midway Airport takes 5h 25m

There are no direct flights from Winnipeg to Chicago Midway Airport. There are no popular flight routes from Winnipeg to Chicago Midway Airport.

Search flight deals

How far is Winnipeg to Chicago Midway by plane?
The distance between Winnipeg and Chicago Midway is about 717.8 mi. A reasonable flight in good conditions will take 5h 25m.
When did momondo last update prices for flights from Winnipeg Airport to Chicago Midway Airport?
Prices for flights from Winnipeg Airport to Chicago Midway Airport are updated daily.
How old do you have to be to fly from Winnipeg Airport to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Winnipeg to Chicago?

Finding the right flight to Chicago from Winnipeg is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Winnipeg to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Winnipeg with this policy.

How can momondo help me find flights from Winnipeg to Chicago?

momondo helps you find the best flight between Winnipeg and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Winnipeg to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Winnipeg to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.