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Cheap flights from Winnipeg to Chicago Midway Airport from $134

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 Midway Airport departing on 5/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Winnipeg to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Winnipeg to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Winnipeg to Chicago.

Cheap last minute flights

Planning a quick getaway from Winnipeg to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Winnipeg to Chicago

Find recent round-trip train or bus tickets from Winnipeg to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
12:45 pm - 5:47 pmYWG-MDW
5h 02m1 stop
6:59 pm - 11:42 pmMDW-YWG
4h 43m1 stop
$454Delta
Find Deal
Mon, Jan 20 - Mon, Jan 27
5:37 pm - 5:47 pmYWG-MDW
24h 10m1 stop
9:34 am - 12:35 amMDW-YWG
15h 01m2 stops
$470WestJet
Find Deal
Mon, Jan 20 - Mon, Jan 27
7:30 am - 4:20 pmYWG-MDW
8h 50m1 stop
6:59 pm - 11:38 pmMDW-YWG
4h 39m1 stop
$483Delta
Find Deal
Tue, Feb 4 - Tue, Feb 25
12:45 pm - 5:43 pmYWG-MDW
4h 58m1 stop
9:25 am - 8:15 pmMDW-YWG
10h 50m2 stops
$498Delta
Find Deal
Sat, Mar 8 - Wed, Mar 12
6:00 am - 5:47 pmYWG-MDW
11h 47m2 stops
12:44 pm - 12:44 amMDW-YWG
12h 00m2 stops
$506WestJet
Find Deal
Mon, Jan 20 - Mon, Jan 27
6:40 am - 12:42 pmYWG-MDW
6h 02m1 stop
5:05 pm - 11:22 amMDW-YWG
18h 17m2 stops
$516WestJet
Find Deal
Tue, Feb 11 - Sun, Feb 16
12:20 pm - 8:51 amYWG-MDW
20h 31m2 stops
5:05 pm - 11:22 amMDW-YWG
18h 17m2 stops
$519WestJet
Find Deal
Tue, Feb 11 - Sun, Feb 16
7:00 pm - 10:32 amYWG-MDW
15h 32m2 stops
11:25 am - 10:45 amMDW-YWG
23h 20m2 stops
Sat, Feb 8 - Sat, Feb 15
11:35 am - 4:40 pmYWG-MDW
29h 05m2 stops
11:15 am - 6:04 pmMDW-YWG
30h 49m2 stops
$627Porter Airlines
Find Deal
Tue, Apr 8 - Sun, Apr 13
6:30 pm - 10:20 amYWG-MDW
15h 50m1 stop
5:15 pm - 11:44 amMDW-YWG
18h 29m1 stop
$807Porter Airlines
Find Deal
Thu, May 22 - Mon, May 26
9:00 am - 5:49 pmYWG-MDW
8h 49m1 stop
Tue, May 13
7:30 am - 4:16 pmYWG-MDW
8h 46m1 stop
Tue, Feb 11
7:00 pm - 12:42 pmYWG-MDW
17h 42m2 stops
Tue, Feb 11
6:30 am - 5:03 pmYWG-MDW
10h 33m2 stops
$274Delta
Find Deal
Tue, May 13
4:25 pm - 12:42 pmYWG-MDW
20h 17m3 stops
$304WestJet
Find Deal
Tue, Feb 11
7:40 pm - 12:30 pmYWG-MDW
16h 50m3 stops
Tue, May 13
12:45 pm - 5:47 pmYWG-MDW
5h 02m1 stop
$454WestJet
Find Deal
Fri, Jan 10
5:00 am - 10:33 pmYWG-MDW
41h 33m2 stops
Mon, Dec 30
12:42 pm - 5:44 pmYWG-MDW
5h 02m1 stop
$520Delta
Find Deal
Mon, Dec 30
12:42 pm - 5:44 pmYWG-MDW
5h 02m1 stop
$657WestJet
Find Deal
Fri, Jan 3
12:42 pm - 11:08 amYWG-MDW
22h 26m1 stop
9:30 am - 11:25 amMDW-YWG
25h 55m2 stops
$901WestJet
Find Deal
Mon, Dec 30 - Fri, Jan 3
12:20 pm - 11:08 amYWG-MDW
22h 48m2 stops
9:30 am - 11:25 amMDW-YWG
25h 55m2 stops
$939WestJet
Find Deal
Mon, Dec 30 - Fri, Jan 3
12:20 pm - 8:50 amYWG-MDW
20h 30m2 stops
9:30 am - 11:25 amMDW-YWG
25h 55m2 stops
$989WestJet
Find Deal
Thu, Dec 26 - Fri, Jan 3
7:15 am - 7:42 pmYWG-MDW
12h 27m1 stop
6:00 am - 6:04 pmMDW-YWG
12h 04m2 stops
$1,104
Find Deal
Thu, Dec 26 - Fri, Jan 3

Delta flights from Winnipeg to Chicago Midway Airport

Our best Delta deals on Winnipeg to Chicago Midway Airport flight tickets
Delta
Jan 20
YWG12:45 pmWinnipeg
5h 02m
1 stop
MDW5:47 pmChicago Midway
Jan 27
MDW6:59 pmChicago Midway
4h 43m
1 stop
YWG11:42 pmWinnipeg
Delta
Feb 4
YWG7:30 amWinnipeg
8h 50m
1 stop
MDW4:20 pmChicago Midway
Feb 25
MDW6:59 pmChicago Midway
4h 39m
1 stop
YWG11:38 pmWinnipeg
Delta
Mar 8
YWG12:45 pmWinnipeg
4h 58m
1 stop
MDW5:43 pmChicago Midway
Mar 12
MDW9:25 amChicago Midway
10h 50m
2 stops
YWG8:15 pmWinnipeg

WestJet flights from Winnipeg to Chicago Midway Airport

Our best WestJet deals on Winnipeg to Chicago Midway Airport flight tickets
WestJet
Jan 20
YWG5:37 pmWinnipeg
24h 10m
1 stop
MDW5:47 pmChicago Midway
Jan 27
MDW9:34 amChicago Midway
15h 01m
2 stops
YWG12:35 amWinnipeg
WestJet
Jan 20
YWG6:00 amWinnipeg
11h 47m
2 stops
MDW5:47 pmChicago Midway
Jan 27
MDW12:44 pmChicago Midway
12h 00m
2 stops
YWG12:44 amWinnipeg
WestJet
Feb 11
YWG6:40 amWinnipeg
6h 02m
1 stop
MDW12:42 pmChicago Midway
Feb 16
MDW5:05 pmChicago Midway
18h 17m
2 stops
YWG11:22 amWinnipeg

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 47% 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

Best Price Found

$134

Fastest flight time

4h 58m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Winnipeg in the past 72 hours is $134. The best round-trip flight deal from Winnipeg to Chicago Midway Airport found on momondo in the last 72 hours is $454.
The fastest flight from Winnipeg to Chicago Midway Airport takes 4h 58m
There are no direct flights from Winnipeg to Chicago Midway Airport. Popular non-direct route for this connection is Winnipeg Airport - 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 58m.

  • 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.


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.


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