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Cheap flights from Winnipeg to Chicago from $126

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 10/31. 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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Find the cheapest flights from Winnipeg to Chicago

Cheap round-trip flights

Logo
9:00 am - 11:46 pmYWG-MDW
14h 46m1 stop
Logo
2:06 pm - 12:41 amMDW-YWG
34h 35m2 stops
$213
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Fri, Oct 17 - Wed, Oct 29
Logo
9:00 pm - 6:39 pmYWG-MDW
21h 39m2 stops
Logo
1:37 pm - 3:07 pmMDW-YWG
25h 30m1 stop
$218
Find Deal
Thu, Oct 30 - Thu, Nov 6
Logo
7:30 am - 6:39 pmYWG-MDW
11h 09m1 stop
Logo
5:20 am - 2:07 pmMDW-YWG
8h 47m1 stop
$231
Find Deal
Fri, Oct 31 - Sun, Nov 2
Logo
9:00 am - 11:46 pmYWG-MDW
14h 46m1 stop
Logo
6:20 am - 3:07 pmMDW-YWG
8h 47m1 stop
$244
Find Deal
Thu, Oct 16 - Sun, Oct 26
Logo
9:00 am - 11:46 pmYWG-MDW
14h 46m1 stop
Logo
9:26 pm - 12:39 amMDW-YWG
27h 13m2 stops
$266
Find Deal
Thu, Oct 16 - Sun, Oct 26
WestJet Logo
6:30 am - 1:03 pmYWG-MDW
30h 33m2 stops
WestJet Logo
9:35 am - 11:10 pmMDW-YWG
13h 35m2 stops
$434WestJet
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Fri, Oct 3 - Sun, Oct 5
WestJet Logo
9:00 pm - 9:40 amYWG-MDW
12h 40m2 stops
WestJet Logo
9:32 am - 7:12 pmMDW-YWG
9h 40m2 stops
$440WestJet
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Mon, Oct 27 - Thu, Nov 20
Delta Logo
6:40 am - 1:08 pmYWG-MDW
6h 28m1 stop
Delta Logo
9:20 am - 4:50 pmMDW-YWG
7h 30m1 stop
$447Delta
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Thu, Oct 9 - Sun, Oct 12
Delta Logo
12:40 pm - 6:08 pmYWG-MDW
5h 28m1 stop
Delta Logo
6:00 am - 3:09 pmMDW-YWG
9h 09m1 stop
$553Delta
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Tue, Mar 3 - Sun, Mar 8
Porter Airlines Logo
11:20 am - 8:39 amYWG-MDW
21h 19m2 stops
Porter Airlines Logo
4:15 pm - 11:13 amMDW-YWG
18h 58m2 stops
$618Porter Airlines
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Thu, Oct 16 - Sun, Oct 26

WestJet flights from Winnipeg to Chicago Midway Airport

Our best WestJet deals on Winnipeg to Chicago Midway Airport flight tickets
WestJet
Oct 3
YWG6:30 amWinnipeg
30h 33m
2 stops
MDW1:03 pmChicago Midway
Oct 5
MDW9:35 amChicago Midway
13h 35m
2 stops
YWG11:10 pmWinnipeg
$434
Find similar
WestJet
Oct 27
YWG9:00 pmWinnipeg
12h 40m
2 stops
MDW9:40 amChicago Midway
Nov 20
MDW9:32 amChicago Midway
9h 40m
2 stops
YWG7:12 pmWinnipeg
$440
Find similar
WestJet
Oct 10
YWG9:00 amWinnipeg
24h 40m
1 stop
MDW9:40 amChicago Midway
Oct 14
MDW9:20 amChicago Midway
26h 10m
1 stop
YWG11:30 amWinnipeg
$503
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Delta flights from Winnipeg to Chicago Midway Airport

Our best Delta deals on Winnipeg to Chicago Midway Airport flight tickets
Delta
Oct 9
YWG6:40 amWinnipeg
6h 28m
1 stop
MDW1:08 pmChicago Midway
Oct 12
MDW9:20 amChicago Midway
7h 30m
1 stop
YWG4:50 pmWinnipeg
$447
Find similar
Delta
Mar 3
YWG12:40 pmWinnipeg
5h 28m
1 stop
MDW6:08 pmChicago Midway
Mar 8
MDW6:00 amChicago Midway
9h 09m
1 stop
YWG3:09 pmWinnipeg
$553
Find similar
Delta
Oct 11
YWG6:40 amWinnipeg
6h 28m
1 stop
MDW1:08 pmChicago Midway
Oct 13
MDW9:20 amChicago Midway
7h 30m
1 stop
YWG4:50 pmWinnipeg
$603
Find similar

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 September 15, 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

Fri 10/17

9:00 am-11:46 pm

1 stop14h 46m

Chicago Midway

Wed 10/29

2:06 pm-12:41 am

2 stops34h 35m

$213

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 10/30

9:00 pm-6:39 pm

2 stops21h 39m

Chicago Midway

Thu 11/6

1:37 pm-3:07 pm

1 stop25h 30m

$218

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 10/31

7:30 am-6:39 pm

1 stop11h 09m

Chicago Midway

Sun 11/2

5:20 am-2:07 pm

1 stop8h 47m

$231

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 10/16

9:00 am-11:46 pm

1 stop14h 46m

Chicago Midway

Sun 10/26

6:20 am-3:07 pm

1 stop8h 47m

$244

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 10/16

9:00 am-11:46 pm

1 stop14h 46m

Chicago Midway

Sun 10/26

9:26 pm-12:39 am

2 stops27h 13m

$266

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 10/3

6:30 am-1:03 pm

2 stops30h 33m

Chicago Midway

Sun 10/5

9:35 am-11:10 pm

2 stops13h 35m

$434

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 10/27

9:00 pm-9:40 am

2 stops12h 40m

Chicago Midway

Thu 11/20

9:32 am-7:12 pm

2 stops9h 40m

$440

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 10/9

6:40 am-1:08 pm

1 stop6h 28m

Chicago Midway

Sun 10/12

9:20 am-4:50 pm

1 stop7h 30m

$447

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 3/3

12:40 pm-6:08 pm

1 stop5h 28m

Chicago Midway

Sun 3/8

6:00 am-3:09 pm

1 stop9h 09m

$553

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 10/16

11:20 am-8:39 am

2 stops21h 19m

Chicago Midway

Sun 10/26

4:15 pm-11:13 am

2 stops18h 58m

$618

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

Direct flights

None
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 3h 50m.

  • 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
Lansing
Portage
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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