How do I get Price Alerts for flights from Winnipeg to Chicago Midway Airport?

Search flight deals from Winnipeg to Chicago Midway Airport . While viewing offers you’ll have the option to create a Price Alert.

How can I save money on flights from Winnipeg to Chicago Midway Airport with momondo?

With “Price Forecast”, learn how soon you should book your flight in advance. Down to the day of week and time of day, our information can inform you on the ideal time to book to save on your travel. Our “Price Calendar” shows you at a quick glance when to book your travel for lower rates. By setting “Price Alerts” you can monitor changes in price and target the ideal time to book. Search for your trip destination by budget amount via our “Explore” feature. Whether you’re looking for ideas for your next travel adventure or cost-cutting tips, our “Discover” content is a great place to start.

How does momondo find its flight prices?

We show prices from over 700+ competitors with a single click. With options from airlines and OTAs from across our 30 international markets, we are able to show you a diverse range of deals to create your adventure.

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.

$126 Cheap Flights from Winnipeg to Chicago Midway Airport in 2025/26

1 adult

0 bags

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Find the cheapest flights from Winnipeg to Chicago

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

12:55 pm - 7:24 pmYWG-MDW

30h 29m2 stops

9:38 am - 3:07 pmMDW-YWG

29h 29m1 stop

$218Multiple Airlines

Find Deal

Sat, Jan 17 - Sat, Jan 24

12:55 pm - 12:05 pmYWG-MDW

23h 10m2 stops

6:20 am - 3:07 pmMDW-YWG

8h 47m1 stop

$253Multiple Airlines

Find Deal

Mon, Jan 19 - Fri, Jan 23

7:30 am - 11:42 pmYWG-MDW

16h 12m1 stop

6:00 am - 3:09 pmMDW-YWG

9h 09m1 stop

$318Multiple Airlines

Find Deal

Fri, Apr 10 - Sun, Apr 12

6:45 am - 6:32 pmYWG-MDW

11h 47m2 stops

5:01 pm - 3:07 pmMDW-YWG

22h 06m1 stop

$361Multiple Airlines

Find Deal

Thu, Jan 15 - Thu, Jan 22

6:45 am - 6:32 pmYWG-MDW

11h 47m2 stops

5:01 pm - 3:07 pmMDW-YWG

22h 06m1 stop

$362Multiple Airlines

Find Deal

Thu, Jan 15 - Thu, Jan 22

5:00 am - 12:48 pmYWG-MDW

7h 48m2 stops

6:10 am - 3:07 pmMDW-YWG

8h 57m1 stop

$369Multiple Airlines

Find Deal

Thu, Jan 15 - Sun, Jan 18

12:20 pm - 7:17 amYWG-MDW

18h 57m2 stops

5:01 pm - 3:07 pmMDW-YWG

22h 06m1 stop

$399Multiple Airlines

Find Deal

Thu, Jan 15 - Thu, Jan 22

5:21 pm - 8:52 amYWG-MDW

15h 31m2 stops

7:16 pm - 11:38 pmMDW-YWG

4h 22m1 stop

$419Delta

Find Deal

Mon, Jan 26 - Wed, Jan 28

6:00 am - 10:05 amYWG-MDW

28h 05m1 stop

2:03 pm - 6:06 pmMDW-YWG

28h 03m2 stops

$421Multiple Airlines

Find Deal

Tue, Dec 23 - Tue, Jan 6

6:45 am - 6:37 pmYWG-MDW

11h 52m2 stops

2:03 pm - 11:35 pmMDW-YWG

9h 32m1 stop

$424WestJet

Find Deal

Tue, Mar 3 - Sun, Mar 8

WestJet flights from Winnipeg to Chicago Midway Airport

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

WestJet

Mar 3

YWG6:45 amWinnipeg

11h 52m

2 stops

MDW6:37 pmChicago Midway

Mar 8

MDW2:03 pmChicago Midway

9h 32m

1 stop

YWG11:35 pmWinnipeg

$424

Find similar

WestJet

Mar 3

YWG11:53 amWinnipeg

6h 44m

1 stop

MDW6:37 pmChicago Midway

Mar 8

MDW9:30 amChicago Midway

14h 05m

1 stop

YWG11:35 pmWinnipeg

$426

Find similar

WestJet

Mar 3

YWG6:45 amWinnipeg

30h 22m

2 stops

MDW1:07 pmChicago Midway

Mar 8

MDW7:20 pmChicago Midway

23h 49m

2 stops

YWG7:09 pmWinnipeg

$428

Find similar

Delta flights from Winnipeg to Chicago Midway Airport

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

Delta

Jan 26

YWG5:21 pmWinnipeg

15h 31m

2 stops

MDW8:52 amChicago Midway

Jan 28

MDW7:16 pmChicago Midway

4h 22m

1 stop

YWG11:38 pmWinnipeg

$419

Find similar

Delta

Jan 15

YWG5:21 pmWinnipeg

25h 11m

1 stop

MDW6:32 pmChicago Midway

Jan 18

MDW1:49 pmChicago Midway

21h 14m

1 stop

YWG11:03 amWinnipeg

$490

Find similar

Delta

Dec 13

YWG12:35 pmWinnipeg

5h 43m

1 stop

MDW6:18 pmChicago Midway

Dec 17

MDW9:59 amChicago Midway

6h 56m

1 stop

YWG4:55 pmWinnipeg

$733

Find similar

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

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 1/17

12:55 pm-7:24 pm

2 stops30h 29m

Chicago Midway

Sat 1/24

9:38 am-3:07 pm

1 stop29h 29m

$218

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 1/19

12:55 pm-12:05 pm

2 stops23h 10m

Chicago Midway

Fri 1/23

6:20 am-3:07 pm

1 stop8h 47m

$253

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 4/10

7:30 am-11:42 pm

1 stop16h 12m

Chicago Midway

Sun 4/12

6:00 am-3:09 pm

1 stop9h 09m

$318

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 1/15

6:45 am-6:32 pm

2 stops11h 47m

Chicago Midway

Thu 1/22

5:01 pm-3:07 pm

1 stop22h 06m

$361

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 1/15

6:45 am-6:32 pm

2 stops11h 47m

Chicago Midway

Thu 1/22

5:01 pm-3:07 pm

1 stop22h 06m

$362

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 1/15

5:00 am-12:48 pm

2 stops7h 48m

Chicago Midway

Sun 1/18

6:10 am-3:07 pm

1 stop8h 57m

$369

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 1/15

12:20 pm-7:17 am

2 stops18h 57m

Chicago Midway

Thu 1/22

5:01 pm-3:07 pm

1 stop22h 06m

$399

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 1/26

5:21 pm-8:52 am

2 stops15h 31m

Chicago Midway

Wed 1/28

7:16 pm-11:38 pm

1 stop4h 22m

$419

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 12/23

6:00 am-10:05 am

1 stop28h 05m

Chicago Midway

Tue 1/6

2:03 pm-6:06 pm

2 stops28h 03m

$421

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 3/3

6:45 am-6:37 pm

2 stops11h 52m

Chicago Midway

Sun 3/8

2:03 pm-11:35 pm

1 stop9h 32m

$424

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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	16h 12m
Direct flights	None

The fastest flight from Winnipeg to Chicago Midway Airport takes 16h 12m

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

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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 4h 44m.
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.

How do I get Price Alerts for flights from Winnipeg to Chicago Midway Airport?
Search flight deals from Winnipeg to Chicago Midway Airport. While viewing offers you’ll have the option to create a Price Alert.
How can I save money on flights from Winnipeg to Chicago Midway Airport with momondo?
With “Price Forecast”, learn how soon you should book your flight in advance. Down to the day of week and time of day, our information can inform you on the ideal time to book to save on your travel. Our “Price Calendar” shows you at a quick glance when to book your travel for lower rates. By setting “Price Alerts” you can monitor changes in price and target the ideal time to book. Search for your trip destination by budget amount via our “Explore” feature. Whether you’re looking for ideas for your next travel adventure or cost-cutting tips, our “Discover” content is a great place to start.
How does momondo find its flight prices?
We show prices from over 700+ competitors with a single click. With options from airlines and OTAs from across our 30 international markets, we are able to show you a diverse range of deals to create your adventure.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

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.