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Cheap flights from Winnipeg to Chicago from $180

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 10/13. 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 - 11:00 am-
16h 55m
Multiple Airlines Logo
11:45 am - 12:55 am-
13h 10m
$327Multiple Airlines
Wed, Sep 23 - Sun, Oct 4
Multiple Airlines Logo
11:15 am - 11:00 am-
23h 45m
Multiple Airlines Logo
3:20 pm - 9:45 am-
18h 25m
$332Multiple Airlines
Wed, Sep 23 - Sun, Oct 4
Multiple Airlines Logo
11:15 am - 11:00 am-
23h 45m
Multiple Airlines Logo
11:45 am - 9:45 am-
22h 00m
$460Multiple Airlines
Wed, Oct 7 - Sun, Oct 11
Multiple Airlines Logo
6:05 pm - 11:00 am-
16h 55m
Multiple Airlines Logo
11:45 am - 9:45 am-
22h 00m
$463Multiple Airlines
Wed, Oct 7 - Sun, Oct 11
Multiple Airlines Logo
11:15 am - 11:00 am-
23h 45m
Multiple Airlines Logo
11:45 am - 12:55 am-
13h 10m
$467Multiple Airlines
Fri, Oct 9 - Sun, Oct 11
Multiple Airlines Logo
7:10 pm - 2:35 pm-
19h 25m
Multiple Airlines Logo
11:45 am - 12:55 am-
13h 10m
$467Multiple Airlines
Wed, Sep 23 - Sun, Oct 4
Multiple Airlines Logo
7:55 pm - 11:00 am-
15h 05m
Multiple Airlines Logo
11:45 am - 12:55 am-
13h 10m
$470Multiple Airlines
Fri, Oct 9 - Sun, Oct 11
Multiple Airlines Logo
11:15 am - 2:35 pm-
27h 20m
Multiple Airlines Logo
10:20 am - 8:20 pm-
10h 00m
$517Multiple Airlines
Sat, Aug 22 - Sat, Aug 29
Multiple Airlines Logo
9:25 am - 2:35 pm-
29h 10m
Multiple Airlines Logo
10:20 am - 8:20 pm-
10h 00m
$521Multiple Airlines
Sat, Aug 22 - Sat, Aug 29
Multiple Airlines Logo
8:10 pm - 11:00 am-
14h 50m
Multiple Airlines Logo
3:20 pm - 12:55 am-
9h 35m
$533Multiple Airlines
Fri, Sep 4 - Mon, Sep 7

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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
Oct 13
YWG6:00 amWinnipeg
12h 00m
2 stops
MDW6:00 pmChicago Midway
Oct 18
MDW1:27 pmChicago Midway
11h 28m
2 stops
YWG12:55 amWinnipeg
$599
WestJet
Oct 13
YWG6:00 amWinnipeg
12h 00m
2 stops
MDW6:00 pmChicago Midway
Oct 18
MDW1:27 pmChicago Midway
11h 28m
2 stops
YWG12:55 amWinnipeg
$600
WestJet
Aug 25
YWG7:00 amWinnipeg
11h 01m
2 stops
MDW6:01 pmChicago Midway
Aug 27
MDW9:24 amChicago Midway
15h 31m
2 stops
YWG12:55 amWinnipeg
$601

Porter Airlines flights from Winnipeg to Chicago Midway Airport

Our best Porter Airlines deals on Winnipeg to Chicago Midway Airport flight tickets
Porter Airlines
Sep 22
YWG11:15 amWinnipeg
23h 45m
2 stops
MDW11:00 amChicago Midway
Sep 25
MDW3:20 pmChicago Midway
26h 38m
2 stops
YWG5:58 pmWinnipeg
$610
Porter Airlines
Sep 10
YWG11:15 amWinnipeg
27h 20m
2 stops
MDW2:35 pmChicago Midway
Sep 17
MDW3:20 pmChicago Midway
26h 38m
2 stops
YWG5:58 pmWinnipeg
$622
Porter Airlines
Sep 2
YWG4:15 pmWinnipeg
22h 20m
2 stops
MDW2:35 pmChicago Midway
Sep 5
MDW3:20 pmChicago Midway
26h 38m
2 stops
YWG5:58 pmWinnipeg
$630

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 August 5, 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

Wed 9/23

6:05 pm-11:00 am

1 stop16h 55m

Chicago Midway

Sun 10/4

11:45 am-12:55 am

1 stop13h 10m

$327

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 9/23

11:15 am-11:00 am

2 stops23h 45m

Chicago Midway

Sun 10/4

3:20 pm-9:45 am

1 stop18h 25m

$332

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 10/7

11:15 am-11:00 am

2 stops23h 45m

Chicago Midway

Sun 10/11

11:45 am-9:45 am

1 stop22h 00m

$460

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 10/7

6:05 pm-11:00 am

1 stop16h 55m

Chicago Midway

Sun 10/11

11:45 am-9:45 am

1 stop22h 00m

$463

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 10/9

11:15 am-11:00 am

2 stops23h 45m

Chicago Midway

Sun 10/11

11:45 am-12:55 am

1 stop13h 10m

$467

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 9/23

7:10 pm-2:35 pm

2 stops19h 25m

Chicago Midway

Sun 10/4

11:45 am-12:55 am

2 stops13h 10m

$467

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 10/9

7:55 pm-11:00 am

1 stop15h 05m

Chicago Midway

Sun 10/11

11:45 am-12:55 am

1 stop13h 10m

$470

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 8/22

11:15 am-2:35 pm

2 stops27h 20m

Chicago Midway

Sat 8/29

10:20 am-8:20 pm

1 stop10h 00m

$517

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 8/22

9:25 am-2:35 pm

1 stop29h 10m

Chicago Midway

Sat 8/29

10:20 am-8:20 pm

1 stop10h 00m

$521
Quickest round-trip

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 9/4

8:10 pm-11:00 am

1 stop14h 50m

Chicago Midway

Mon 9/7

3:20 pm-12:55 am

1 stop9h 35m

$533

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 2% 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 20m

Direct flights

None
The fastest flight from Winnipeg to Chicago Midway Airport takes 4h 20m
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 20m.

  • 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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