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Cheap flights from Winnipeg to Chicago from $222

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Chicago departing on 8/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Delta Logo
6:40 am - 12:28 pmYWG-MDW
5h 48m2 stops
Delta Logo
1:08 pm - 11:27 pmMDW-YWG
10h 19m2 stops
$359Delta
Find Deal
Sat, Sep 13 - Sat, Sep 20
Delta Logo
12:43 pm - 5:37 pmYWG-MDW
4h 54m1 stop
Delta Logo
6:00 am - 4:51 pmMDW-YWG
10h 51m2 stops
$374Delta
Find Deal
Wed, Aug 27 - Wed, Sep 3
Delta Logo
6:40 am - 12:28 pmYWG-MDW
5h 48m2 stops
Delta Logo
9:20 am - 4:50 pmMDW-YWG
7h 30m1 stop
$381Delta
Find Deal
Sat, Sep 13 - Sat, Sep 20
Delta Logo
6:40 am - 12:28 pmYWG-MDW
5h 48m2 stops
Delta Logo
1:08 pm - 11:27 pmMDW-YWG
10h 19m2 stops
$404Delta
Find Deal
Sat, Sep 13 - Sat, Sep 20
Delta Logo
8:35 am - 5:35 pmYWG-MDW
9h 00m1 stop
Delta Logo
7:15 pm - 11:27 pmMDW-YWG
4h 12m1 stop
$405Delta
Find Deal
Fri, Sep 19 - Tue, Sep 23
WestJet Logo
9:05 pm - 9:36 amYWG-MDW
12h 31m2 stops
WestJet Logo
12:43 pm - 12:31 amMDW-YWG
11h 48m2 stops
$436WestJet
Find Deal
Tue, Aug 19 - Wed, Aug 20
WestJet Logo
8:15 pm - 9:36 amYWG-MDW
13h 21m2 stops
WestJet Logo
9:15 am - 9:26 pmMDW-YWG
12h 11m2 stops
$441WestJet
Find Deal
Tue, Aug 19 - Tue, Aug 26
Logo
6:55 pm - 8:45 amYWG-MDW
13h 50m1 stop
Logo
5:20 pm - 9:41 amMDW-YWG
16h 21m1 stop
$485
Find Deal
Wed, Aug 27 - Wed, Sep 3
Logo
6:30 am - 4:24 pmYWG-MDW
9h 54m1 stop
Logo
5:20 pm - 9:41 amMDW-YWG
16h 21m1 stop
$488
Find Deal
Thu, Aug 28 - Tue, Sep 2
Porter Airlines Logo
11:20 am - 4:24 pmYWG-MDW
29h 04m2 stops
Porter Airlines Logo
5:20 pm - 10:25 amMDW-YWG
17h 05m2 stops
$587Porter Airlines
Find Deal
Thu, Oct 16 - Sun, Oct 19

WestJet flights from Winnipeg to Chicago Midway Airport

Our best WestJet deals on Winnipeg to Chicago Midway Airport flight tickets
WestJet
Aug 19
YWG9:05 pmWinnipeg
12h 31m
2 stops
MDW9:36 amChicago Midway
Aug 20
MDW12:43 pmChicago Midway
11h 48m
2 stops
YWG12:31 amWinnipeg
$436
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WestJet
Aug 19
YWG8:15 pmWinnipeg
13h 21m
2 stops
MDW9:36 amChicago Midway
Aug 26
MDW9:15 amChicago Midway
12h 11m
2 stops
YWG9:26 pmWinnipeg
$441
Find similar
WestJet
Aug 19
YWG8:15 pmWinnipeg
13h 21m
2 stops
MDW9:36 amChicago Midway
Aug 26
MDW9:15 amChicago Midway
14h 12m
1 stop
YWG11:27 pmWinnipeg
$444
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Porter Airlines flights from Winnipeg to Chicago Midway Airport

Our best Porter Airlines deals on Winnipeg to Chicago Midway Airport flight tickets
Porter Airlines
Oct 16
YWG11:20 amWinnipeg
29h 04m
2 stops
MDW4:24 pmChicago Midway
Oct 19
MDW5:20 pmChicago Midway
17h 05m
2 stops
YWG10:25 amWinnipeg
$587
Find similar
Porter Airlines
Aug 3
YWG11:45 amWinnipeg
21h 00m
2 stops
MDW8:45 amChicago Midway
Aug 9
MDW9:40 amChicago Midway
13h 06m
2 stops
YWG10:46 pmWinnipeg
$1,112
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momondo Fare Finder

 
Customize your flight search to find flights from Winnipeg to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated July 31, 2025.
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 9/13

6:40 am-12:28 pm

2 stops5h 48m

Chicago Midway

Sat 9/20

1:08 pm-11:27 pm

2 stops10h 19m

$359

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 8/27

12:43 pm-5:37 pm

1 stop4h 54m

Chicago Midway

Wed 9/3

6:00 am-4:51 pm

2 stops10h 51m

$374

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 9/13

6:40 am-12:28 pm

2 stops5h 48m

Chicago Midway

Sat 9/20

9:20 am-4:50 pm

1 stop7h 30m

$381

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 9/13

6:40 am-12:28 pm

2 stops5h 48m

Chicago Midway

Sat 9/20

1:08 pm-11:27 pm

2 stops10h 19m

$404

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 9/19

8:35 am-5:35 pm

1 stop9h 00m

Chicago Midway

Tue 9/23

7:15 pm-11:27 pm

1 stop4h 12m

$405

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 8/19

9:05 pm-9:36 am

2 stops12h 31m

Chicago Midway

Wed 8/20

12:43 pm-12:31 am

2 stops11h 48m

$436

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 8/19

8:15 pm-9:36 am

2 stops13h 21m

Chicago Midway

Tue 8/26

9:15 am-9:26 pm

2 stops12h 11m

$441

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 8/27

6:55 pm-8:45 am

1 stop13h 50m

Chicago Midway

Wed 9/3

5:20 pm-9:41 am

1 stop16h 21m

$485

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 8/28

6:30 am-4:24 pm

1 stop9h 54m

Chicago Midway

Tue 9/2

5:20 pm-9:41 am

1 stop16h 21m

$488

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 10/16

11:20 am-4:24 pm

2 stops29h 04m

Chicago Midway

Sun 10/19

5:20 pm-10:25 am

2 stops17h 05m

$587

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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

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

Delta, WestJet, and Porter Airlines are the most popular carriers operating from Winnipeg to Chicago Midway

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

Best Price Found

$222

Fastest flight time

3h 50m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Winnipeg in the past 72 hours is $222. The best round-trip flight deal from Winnipeg to Chicago Midway Airport found on momondo in the last 72 hours is $359.
The fastest flight from Winnipeg to Chicago Midway Airport takes 3h 50m
There are no direct flights from Winnipeg to Chicago Midway Airport. Popular non-direct route for this connection is Winnipeg Airport - 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 54m.

  • 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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.

An easier way to manage your Chicago Midway Airport trip

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