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Cheap flights from Winnipeg to Chicago from $211

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 6/14. 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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Find the cheapest flights from Winnipeg to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
8:45 pm - 9:35 am
YWG
-
MDW
12h 50m
1 stop
Multiple Airlines Logo
3:20 pm - 9:45 am
MDW
-
YWG
18h 25m
1 stop
$436Multiple Airlines
Mon, Jun 1 - Mon, Jun 8
Multiple Airlines Logo
11:40 am - 9:35 am
YWG
-
MDW
21h 55m
2 stops
Multiple Airlines Logo
10:15 am - 8:40 am
MDW
-
YWG
22h 25m
1 stop
$440Multiple Airlines
Thu, Jun 4 - Sun, Jun 7
Multiple Airlines Logo
8:45 pm - 9:35 am
YWG
-
MDW
12h 50m
1 stop
Multiple Airlines Logo
10:15 am - 8:40 am
MDW
-
YWG
22h 25m
1 stop
$459Multiple Airlines
Thu, Jun 4 - Sun, Jun 7
Multiple Airlines Logo
9:05 pm - 11:12 am
YWG
-
MDW
14h 07m
2 stops
Multiple Airlines Logo
10:15 am - 7:25 pm
MDW
-
YWG
9h 10m
1 stop
$460Multiple Airlines
Mon, Jun 1 - Mon, Jun 8
Delta Logo
6:40 am - 9:09 pm
YWG
-
MDW
14h 29m
2 stops
Delta Logo
5:12 pm - 2:55 pm
MDW
-
YWG
21h 43m
2 stops
$496Delta
Sat, May 23 - Wed, May 27
Delta Logo
6:40 am - 9:09 pm
YWG
-
MDW
14h 29m
2 stops
Delta Logo
5:12 pm - 2:55 pm
MDW
-
YWG
21h 43m
2 stops
$498Delta
Sat, May 23 - Wed, May 27
Delta Logo
5:41 pm - 9:14 am
YWG
-
MDW
15h 33m
2 stops
Delta Logo
6:58 pm - 3:04 pm
MDW
-
YWG
20h 06m
2 stops
$506Delta
Tue, Jun 23 - Tue, Jun 30
Delta Logo
6:40 am - 6:31 pm
YWG
-
MDW
11h 51m
2 stops
Delta Logo
6:58 pm - 3:04 pm
MDW
-
YWG
20h 06m
2 stops
$523Delta
Tue, Jun 23 - Tue, Jun 30
WestJet Logo
7:00 am - 6:31 pm
YWG
-
MDW
11h 31m
2 stops
WestJet Logo
5:59 pm - 2:25 pm
MDW
-
YWG
20h 26m
2 stops
$532WestJet
Tue, Aug 25 - Sat, Aug 29
WestJet Logo
6:15 am - 9:46 pm
YWG
-
MDW
15h 31m
2 stops
WestJet Logo
5:59 pm - 2:25 pm
MDW
-
YWG
20h 26m
2 stops
$534WestJet
Tue, Aug 25 - Sat, Aug 29

WestJet flights from Winnipeg to Chicago Midway Airport

Our best WestJet deals on Winnipeg to Chicago Midway Airport flight tickets
WestJet
Aug 25
YWG7:00 amWinnipeg
11h 31m
2 stops
MDW6:31 pmChicago Midway
Aug 29
MDW5:59 pmChicago Midway
20h 26m
2 stops
YWG2:25 pmWinnipeg
$532
WestJet
Aug 25
YWG6:15 amWinnipeg
15h 31m
2 stops
MDW9:46 pmChicago Midway
Aug 29
MDW5:59 pmChicago Midway
20h 26m
2 stops
YWG2:25 pmWinnipeg
$534
WestJet
Jun 23
YWG12:46 pmWinnipeg
5h 32m
1 stop
MDW6:18 pmChicago Midway
Jun 30
MDW1:49 pmChicago Midway
25h 15m
1 stop
YWG3:04 pmWinnipeg
$544

Delta flights from Winnipeg to Chicago Midway Airport

Our best Delta deals on Winnipeg to Chicago Midway Airport flight tickets
Delta
May 23
YWG6:40 amWinnipeg
14h 29m
2 stops
MDW9:09 pmChicago Midway
May 27
MDW5:12 pmChicago Midway
21h 43m
2 stops
YWG2:55 pmWinnipeg
$496
Delta
May 23
YWG6:40 amWinnipeg
14h 29m
2 stops
MDW9:09 pmChicago Midway
May 27
MDW5:12 pmChicago Midway
21h 43m
2 stops
YWG2:55 pmWinnipeg
$498
Delta
Jun 23
YWG5:41 pmWinnipeg
15h 33m
2 stops
MDW9:14 amChicago Midway
Jun 30
MDW6:58 pmChicago Midway
20h 06m
2 stops
YWG3:04 pmWinnipeg
$506

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 May 4, 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

Mon 6/1

8:45 pm-9:35 am

1 stop12h 50m

Chicago Midway

Mon 6/8

3:20 pm-9:45 am

1 stop18h 25m

$436

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 6/4

11:40 am-9:35 am

2 stops21h 55m

Chicago Midway

Sun 6/7

10:15 am-8:40 am

1 stop22h 25m

$440

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 6/4

8:45 pm-9:35 am

1 stop12h 50m

Chicago Midway

Sun 6/7

10:15 am-8:40 am

1 stop22h 25m

$459
Quickest round-trip

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 6/1

9:05 pm-11:12 am

2 stops14h 07m

Chicago Midway

Mon 6/8

10:15 am-7:25 pm

1 stop9h 10m

$460

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 5/23

6:40 am-9:09 pm

2 stops14h 29m

Chicago Midway

Wed 5/27

5:12 pm-2:55 pm

2 stops21h 43m

$496

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 5/23

6:40 am-9:09 pm

2 stops14h 29m

Chicago Midway

Wed 5/27

5:12 pm-2:55 pm

2 stops21h 43m

$498

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 6/23

5:41 pm-9:14 am

2 stops15h 33m

Chicago Midway

Tue 6/30

6:58 pm-3:04 pm

2 stops20h 06m

$506

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 6/23

6:40 am-6:31 pm

2 stops11h 51m

Chicago Midway

Tue 6/30

6:58 pm-3:04 pm

2 stops20h 06m

$523

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 8/25

7:00 am-6:31 pm

2 stops11h 31m

Chicago Midway

Sat 8/29

5:59 pm-2:25 pm

2 stops20h 26m

$532

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 8/25

6:15 am-9:46 pm

2 stops15h 31m

Chicago Midway

Sat 8/29

5:59 pm-2:25 pm

2 stops20h 26m

$534

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

9h 50m

Direct flights

None
The fastest flight from Winnipeg to Chicago Midway Airport takes 9h 50m
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 9h 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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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