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Cheap flights from Winnipeg to Chicago from $201

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 7/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Winnipeg to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:05 pm - 9:40 am
YWG
-
MDW
15h 35m
1 stop
Multiple Airlines Logo
3:20 pm - 5:58 pm
MDW
-
YWG
26h 38m
2 stops
$370Multiple Airlines
Tue, Jul 14 - Fri, Jul 17
Multiple Airlines Logo
6:05 pm - 9:40 am
YWG
-
MDW
15h 35m
1 stop
Multiple Airlines Logo
3:20 pm - 9:45 am
MDW
-
YWG
18h 25m
1 stop
$377Multiple Airlines
Tue, Jul 14 - Fri, Jul 17
Multiple Airlines Logo
8:45 pm - 9:40 am
YWG
-
MDW
12h 55m
1 stop
Multiple Airlines Logo
3:15 pm - 12:15 pm
MDW
-
YWG
21h 00m
2 stops
$390Multiple Airlines
Thu, Aug 20 - Tue, Aug 25
Multiple Airlines Logo
8:45 pm - 9:40 am
YWG
-
MDW
12h 55m
1 stop
Multiple Airlines Logo
3:15 pm - 9:45 am
MDW
-
YWG
18h 30m
1 stop
$391Multiple Airlines
Thu, Aug 20 - Tue, Aug 25
Multiple Airlines Logo
6:05 pm - 9:40 am
YWG
-
MDW
15h 35m
1 stop
Multiple Airlines Logo
3:20 pm - 9:45 am
MDW
-
YWG
18h 25m
1 stop
$416Multiple Airlines
Fri, Jul 17 - Sun, Jul 19
Multiple Airlines Logo
8:10 pm - 9:40 am
YWG
-
MDW
13h 30m
1 stop
Multiple Airlines Logo
3:15 pm - 12:15 pm
MDW
-
YWG
21h 00m
2 stops
$436Multiple Airlines
Wed, Aug 19 - Tue, Aug 25
Multiple Airlines Logo
8:45 pm - 9:40 am
YWG
-
MDW
12h 55m
1 stop
Multiple Airlines Logo
3:15 pm - 2:05 pm
MDW
-
YWG
22h 50m
2 stops
$437Multiple Airlines
Thu, Aug 20 - Mon, Aug 24
Multiple Airlines Logo
8:10 pm - 9:40 am
YWG
-
MDW
13h 30m
1 stop
Multiple Airlines Logo
3:15 pm - 9:45 am
MDW
-
YWG
18h 30m
1 stop
$438Multiple Airlines
Wed, Aug 19 - Tue, Aug 25
Multiple Airlines Logo
4:15 pm - 9:40 am
YWG
-
MDW
17h 25m
2 stops
Multiple Airlines Logo
3:15 pm - 9:45 am
MDW
-
YWG
18h 30m
1 stop
$445Multiple Airlines
Fri, Aug 21 - Tue, Aug 25
Multiple Airlines Logo
4:55 pm - 9:40 am
YWG
-
MDW
16h 45m
2 stops
Multiple Airlines Logo
3:20 pm - 12:55 am
MDW
-
YWG
9h 35m
1 stop
$450Multiple Airlines
Fri, Jul 17 - Mon, Jul 20

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WestJet flights from Winnipeg to Chicago Midway Airport

Our best WestJet deals on Winnipeg to Chicago Midway Airport flight tickets
WestJet
Sep 12
YWG6:15 amWinnipeg
9h 10m
2 stops
MDW3:25 pmChicago Midway
Sep 14
MDW10:48 amChicago Midway
9h 32m
2 stops
YWG8:20 pmWinnipeg
$547
WestJet
Aug 27
YWG7:00 amWinnipeg
11h 33m
2 stops
MDW6:33 pmChicago Midway
Aug 30
MDW1:27 pmChicago Midway
11h 28m
2 stops
YWG12:55 amWinnipeg
$565
WestJet
Sep 13
YWG10:45 amWinnipeg
7h 46m
2 stops
MDW6:31 pmChicago Midway
Sep 14
MDW10:48 amChicago Midway
9h 32m
2 stops
YWG8:20 pmWinnipeg
$566

Porter Airlines flights from Winnipeg to Chicago Midway Airport

Our best Porter Airlines deals on Winnipeg to Chicago Midway Airport flight tickets
Porter Airlines
Jul 17
YWG11:40 amWinnipeg
22h 00m
2 stops
MDW9:40 amChicago Midway
Jul 19
MDW3:20 pmChicago Midway
26h 38m
2 stops
YWG5:58 pmWinnipeg
$552
Porter Airlines
Jul 10
YWG11:40 amWinnipeg
22h 00m
2 stops
MDW9:40 amChicago Midway
Jul 14
MDW10:25 amChicago Midway
24h 18m
2 stops
YWG10:43 amWinnipeg
$570
Porter Airlines
Jul 3
YWG4:15 pmWinnipeg
17h 25m
2 stops
MDW9:40 amChicago Midway
Jul 7
MDW10:25 amChicago Midway
24h 18m
2 stops
YWG10:43 amWinnipeg
$599

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 June 19, 2026.
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

Tue 7/14

6:05 pm-9:40 am

1 stop15h 35m

Chicago Midway

Fri 7/17

3:20 pm-5:58 pm

2 stops26h 38m

$370

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 7/14

6:05 pm-9:40 am

1 stop15h 35m

Chicago Midway

Fri 7/17

3:20 pm-9:45 am

1 stop18h 25m

$377

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 8/20

8:45 pm-9:40 am

1 stop12h 55m

Chicago Midway

Tue 8/25

3:15 pm-12:15 pm

2 stops21h 00m

$390

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 8/20

8:45 pm-9:40 am

1 stop12h 55m

Chicago Midway

Tue 8/25

3:15 pm-9:45 am

1 stop18h 30m

$391

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 7/17

6:05 pm-9:40 am

1 stop15h 35m

Chicago Midway

Sun 7/19

3:20 pm-9:45 am

1 stop18h 25m

$416

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 8/19

8:10 pm-9:40 am

1 stop13h 30m

Chicago Midway

Tue 8/25

3:15 pm-12:15 pm

2 stops21h 00m

$436

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 8/20

8:45 pm-9:40 am

1 stop12h 55m

Chicago Midway

Mon 8/24

3:15 pm-2:05 pm

2 stops22h 50m

$437

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 8/19

8:10 pm-9:40 am

1 stop13h 30m

Chicago Midway

Tue 8/25

3:15 pm-9:45 am

1 stop18h 30m

$438

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 8/21

4:15 pm-9:40 am

2 stops17h 25m

Chicago Midway

Tue 8/25

3:15 pm-9:45 am

1 stop18h 30m

$445
Quickest round-trip

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 7/17

4:55 pm-9:40 am

2 stops16h 45m

Chicago Midway

Mon 7/20

3:20 pm-12:55 am

1 stop9h 35m

$450

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

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

4h 21m

Direct flights

None
The fastest flight from Winnipeg to Chicago Midway Airport takes 4h 21m
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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Frequently asked questions about flying from Winnipeg to Chicago Midway Airport

  • 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 21m.

  • 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
Portage
Saint Joseph
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.

An easier way to manage your Chicago Midway Airport trip

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