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Cheap flights from Winnipeg to Chicago from $155

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 3/13. 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
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:30 am - 7:47 pm
YWG
-
MDW
12h 17m
1 stop
Multiple Airlines Logo
6:00 am - 12:40 am
MDW
-
YWG
18h 40m
2 stops
$320Multiple Airlines
Fri, Mar 6 - Tue, Mar 10
Multiple Airlines Logo
7:30 am - 7:07 pm
YWG
-
MDW
11h 37m
1 stop
Multiple Airlines Logo
7:15 am - 12:40 am
MDW
-
YWG
17h 25m
2 stops
$348Multiple Airlines
Wed, Feb 25 - Wed, Mar 4
Multiple Airlines Logo
7:30 am - 7:47 pm
YWG
-
MDW
12h 17m
1 stop
Multiple Airlines Logo
9:51 pm - 11:32 am
MDW
-
YWG
37h 41m
2 stops
$359Multiple Airlines
Fri, Mar 6 - Mon, Mar 9
Multiple Airlines Logo
7:30 am - 7:07 pm
YWG
-
MDW
11h 37m
1 stop
Multiple Airlines Logo
7:15 am - 3:09 pm
MDW
-
YWG
7h 54m
1 stop
$391Multiple Airlines
Wed, Feb 25 - Wed, Mar 4
Multiple Airlines Logo
7:30 am - 10:19 pm
YWG
-
MDW
14h 49m
1 stop
Multiple Airlines Logo
11:00 am - 11:13 am
MDW
-
YWG
24h 13m
2 stops
$398Multiple Airlines
Fri, Mar 13 - Fri, Mar 20
Multiple Airlines Logo
7:30 am - 10:19 pm
YWG
-
MDW
14h 49m
1 stop
Multiple Airlines Logo
6:05 am - 3:09 pm
MDW
-
YWG
9h 04m
1 stop
$401Multiple Airlines
Fri, Mar 13 - Fri, Mar 20
Multiple Airlines Logo
7:30 am - 10:19 pm
YWG
-
MDW
14h 49m
1 stop
Multiple Airlines Logo
1:10 pm - 12:39 am
MDW
-
YWG
11h 29m
2 stops
$409Multiple Airlines
Fri, Mar 13 - Mon, Mar 30
Multiple Airlines Logo
8:20 pm - 10:05 am
YWG
-
MDW
13h 45m
1 stop
Multiple Airlines Logo
9:51 pm - 11:32 am
MDW
-
YWG
37h 41m
2 stops
$418Multiple Airlines
Thu, Mar 5 - Mon, Mar 9
WestJet Logo
5:19 pm - 4:14 pm
YWG
-
MDW
22h 55m
1 stop
WestJet Logo
9:30 am - 4:23 pm
MDW
-
YWG
6h 53m
1 stop
$451WestJet
Fri, Mar 6 - Mon, Mar 9
WestJet Logo
5:00 am - 5:45 pm
YWG
-
MDW
12h 45m
2 stops
WestJet Logo
6:34 pm - 7:09 pm
MDW
-
YWG
24h 35m
2 stops
$453WestJet
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 6
YWG5:19 pmWinnipeg
22h 55m
1 stop
MDW4:14 pmChicago Midway
Mar 9
MDW9:30 amChicago Midway
6h 53m
1 stop
YWG4:23 pmWinnipeg
$451
WestJet
Mar 3
YWG5:00 amWinnipeg
12h 45m
2 stops
MDW5:45 pmChicago Midway
Mar 8
MDW6:34 pmChicago Midway
24h 35m
2 stops
YWG7:09 pmWinnipeg
$453
WestJet
Feb 25
YWG5:00 amWinnipeg
12h 37m
2 stops
MDW5:37 pmChicago Midway
Mar 4
MDW7:20 pmChicago Midway
23h 49m
2 stops
YWG7:09 pmWinnipeg
$454

Porter Airlines flights from Winnipeg to Chicago Midway Airport

Our best Porter Airlines deals on Winnipeg to Chicago Midway Airport flight tickets
Porter Airlines
Mar 6
YWG4:25 pmWinnipeg
19h 25m
2 stops
MDW11:50 amChicago Midway
Mar 9
MDW11:00 amChicago Midway
24h 13m
2 stops
YWG11:13 amWinnipeg
$655
Porter Airlines
Jun 13
YWG4:15 pmWinnipeg
24h 35m
2 stops
MDW4:50 pmChicago Midway
Jun 16
MDW5:35 pmChicago Midway
24h 23m
2 stops
YWG5:58 pmWinnipeg
$2,469

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 January 29, 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

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 3/6

7:30 am-7:47 pm

1 stop12h 17m

Chicago Midway

Tue 3/10

6:00 am-12:40 am

2 stops18h 40m

$320

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 2/25

7:30 am-7:07 pm

1 stop11h 37m

Chicago Midway

Wed 3/4

7:15 am-12:40 am

2 stops17h 25m

$348

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 3/6

7:30 am-7:47 pm

1 stop12h 17m

Chicago Midway

Mon 3/9

9:51 pm-11:32 am

2 stops37h 41m

$359

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 2/25

7:30 am-7:07 pm

1 stop11h 37m

Chicago Midway

Wed 3/4

7:15 am-3:09 pm

1 stop7h 54m

$391

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 3/13

7:30 am-10:19 pm

1 stop14h 49m

Chicago Midway

Fri 3/20

11:00 am-11:13 am

2 stops24h 13m

$398

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 3/13

7:30 am-10:19 pm

1 stop14h 49m

Chicago Midway

Fri 3/20

6:05 am-3:09 pm

1 stop9h 04m

$401

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 3/13

7:30 am-10:19 pm

1 stop14h 49m

Chicago Midway

Mon 3/30

1:10 pm-12:39 am

2 stops11h 29m

$409

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 3/5

8:20 pm-10:05 am

1 stop13h 45m

Chicago Midway

Mon 3/9

9:51 pm-11:32 am

2 stops37h 41m

$418

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 3/6

5:19 pm-4:14 pm

1 stop22h 55m

Chicago Midway

Mon 3/9

9:30 am-4:23 pm

1 stop6h 53m

$451

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 3/3

5:00 am-5:45 pm

2 stops12h 45m

Chicago Midway

Sun 3/8

6:34 pm-7:09 pm

2 stops24h 35m

$453

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

6h 27m

Direct flights

None
The fastest flight from Winnipeg to Chicago Midway Airport takes 6h 27m
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 6h 27m.

  • 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
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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