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Cheap flights from Winnipeg to Chicago Midway Airport from $137

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 11/18. 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

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.
6:55 am - 1:31 pmYWG-MDW
6h 36m1 stop
2:15 pm - 11:34 pmMDW-YWG
9h 19m1 stop
$420Delta
Find Deal
Tue, Dec 10 - Thu, Dec 12
6:55 am - 1:35 pmYWG-MDW
6h 40m1 stop
7:17 pm - 11:27 pmMDW-YWG
4h 10m1 stop
$443Delta
Find Deal
Wed, Nov 27 - Tue, Dec 3
5:15 pm - 11:10 amYWG-MDW
17h 55m2 stops
11:25 am - 9:09 pmMDW-YWG
9h 44m2 stops
Tue, Dec 10 - Thu, Dec 12
6:55 am - 5:44 pmYWG-MDW
10h 49m1 stop
4:50 pm - 11:52 amMDW-YWG
19h 02m1 stop
$472WestJet
Find Deal
Fri, Dec 20 - Wed, Dec 25
6:55 am - 6:14 pmYWG-MDW
11h 19m2 stops
6:00 am - 3:08 pmMDW-YWG
9h 08m1 stop
$473Delta
Find Deal
Tue, Feb 4 - Sun, Feb 9
5:00 am - 1:08 pmYWG-MDW
8h 08m2 stops
6:00 am - 3:08 pmMDW-YWG
9h 08m1 stop
$479Delta
Find Deal
Mon, Feb 3 - Sun, Feb 9
7:30 am - 9:32 amYWG-MDW
26h 02m1 stop
9:38 am - 11:34 pmMDW-YWG
13h 56m1 stop
$482WestJet
Find Deal
Tue, Nov 26 - Sat, Dec 7
7:30 am - 10:12 amYWG-MDW
26h 42m1 stop
1:26 pm - 11:55 amMDW-YWG
22h 29m1 stop
$484WestJet
Find Deal
Mon, Feb 3 - Tue, Feb 4
6:45 pm - 12:00 pmYWG-MDW
17h 15m1 stop
11:15 am - 10:45 amMDW-YWG
23h 30m1 stop
$535Porter Airlines
Find Deal
Fri, Nov 22 - Tue, Nov 26
11:35 am - 12:00 pmYWG-MDW
24h 25m2 stops
11:15 am - 10:45 amMDW-YWG
23h 30m1 stop
$567Porter Airlines
Find Deal
Fri, Nov 22 - Tue, Nov 26
7:30 am - 10:38 amYWG-MDW
27h 08m1 stop
Mon, Nov 18
7:30 am - 5:12 pmYWG-MDW
9h 42m1 stop
Fri, Dec 6
5:00 pm - 10:23 amYWG-MDW
17h 23m2 stops
Mon, Nov 18
7:30 am - 4:56 pmYWG-MDW
9h 26m1 stop
Sun, Dec 8
6:55 am - 1:35 pmYWG-MDW
6h 40m1 stop
$260Delta
Find Deal
Mon, Nov 25
5:00 am - 12:50 pmYWG-MDW
31h 50m2 stops
$269WestJet
Find Deal
Sun, Dec 8
7:00 pm - 12:00 pmYWG-MDW
17h 00m1 stop
$273Porter Airlines
Find Deal
Thu, Jan 9
11:35 am - 12:00 pmYWG-MDW
24h 25m2 stops
$278Porter Airlines
Find Deal
Thu, Jan 9
8:00 pm - 1:35 pmYWG-MDW
17h 35m2 stops
$297WestJet
Find Deal
Tue, Nov 19
6:55 am - 5:02 pmYWG-MDW
10h 07m2 stops
$350Delta
Find Deal
Sat, Nov 16
8:15 pm - 10:20 amYWG-MDW
14h 05m1 stop
11:15 am - 9:09 pmMDW-YWG
9h 54m2 stops
Sat, Nov 9 - Tue, Nov 12
8:15 pm - 10:20 amYWG-MDW
14h 05m1 stop
11:15 am - 9:09 pmMDW-YWG
9h 54m2 stops
Sat, Nov 9 - Mon, Nov 11
5:00 am - 4:40 pmYWG-MDW
11h 40m1 stop
11:18 am - 12:43 amMDW-YWG
13h 25m1 stop
Thu, Nov 7 - Sun, Nov 10
6:45 pm - 10:20 amYWG-MDW
15h 35m1 stop
5:35 pm - 10:45 amMDW-YWG
17h 10m1 stop
$867Porter Airlines
Find Deal
Sat, Nov 9 - Sun, Nov 10
5:00 am - 4:40 pmYWG-MDW
11h 40m1 stop
11:15 am - 10:45 amMDW-YWG
23h 30m1 stop
$885Porter Airlines
Find Deal
Thu, Nov 7 - Tue, Nov 12
5:00 am - 4:40 pmYWG-MDW
11h 40m1 stop
11:15 am - 9:09 pmMDW-YWG
9h 54m2 stops
$903Porter Airlines
Find Deal
Thu, Nov 7 - Tue, Nov 12
5:00 am - 6:29 pmYWG-MDW
13h 29m2 stops
11:15 am - 9:09 pmMDW-YWG
9h 54m2 stops
Thu, Nov 7 - Tue, Nov 12
5:00 am - 6:29 pmYWG-MDW
13h 29m2 stops
11:15 am - 10:45 amMDW-YWG
23h 30m1 stop
Thu, Nov 7 - Sun, Nov 10
6:45 pm - 12:00 pmYWG-MDW
17h 15m1 stop
11:15 am - 10:45 amMDW-YWG
23h 30m1 stop
$961Porter Airlines
Find Deal
Fri, Nov 8 - Tue, Nov 12
8:25 pm - 9:59 amYWG-MDW
13h 34m2 stops
12:43 pm - 12:35 amMDW-YWG
11h 52m2 stops
$1,360WestJet
Find Deal
Sat, Nov 9 - Mon, Nov 11

Delta flights from Winnipeg to Chicago Midway Airport

Our best Delta deals on Winnipeg to Chicago Midway Airport flight tickets
Delta
Dec 10
YWG6:55 amWinnipeg
6h 36m
1 stop
MDW1:31 pmChicago Midway
Dec 12
MDW2:15 pmChicago Midway
9h 19m
1 stop
YWG11:34 pmWinnipeg
Delta
Nov 27
YWG6:55 amWinnipeg
6h 40m
1 stop
MDW1:35 pmChicago Midway
Dec 3
MDW7:17 pmChicago Midway
4h 10m
1 stop
YWG11:27 pmWinnipeg
Delta
Feb 4
YWG6:55 amWinnipeg
11h 19m
2 stops
MDW6:14 pmChicago Midway
Feb 9
MDW6:00 amChicago Midway
9h 08m
1 stop
YWG3:08 pmWinnipeg

WestJet flights from Winnipeg to Chicago Midway Airport

Our best WestJet deals on Winnipeg to Chicago Midway Airport flight tickets
WestJet
Dec 20
YWG6:55 amWinnipeg
10h 49m
1 stop
MDW5:44 pmChicago Midway
Dec 25
MDW4:50 pmChicago Midway
19h 02m
1 stop
YWG11:52 amWinnipeg
WestJet
Nov 26
YWG7:30 amWinnipeg
26h 02m
1 stop
MDW9:32 amChicago Midway
Dec 7
MDW9:38 amChicago Midway
13h 56m
1 stop
YWG11:34 pmWinnipeg
WestJet
Feb 3
YWG7:30 amWinnipeg
26h 42m
1 stop
MDW10:12 amChicago Midway
Feb 4
MDW1:26 pmChicago Midway
22h 29m
1 stop
YWG11:55 amWinnipeg

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 26% 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

$137

Fastest flight time

5h 02m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Winnipeg in the past 72 hours is $137. The best round-trip flight deal from Winnipeg to Chicago Midway Airport found on momondo in the last 72 hours is $420.
The fastest flight from Winnipeg to Chicago Midway Airport takes 5h 02m
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 5h 02m.

  • 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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