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Cheap flights from Winnipeg to Chicago Midway Airport from $141

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 1/10. 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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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.
7:30 am - 4:14 pmYWG-MDW
8h 44m1 stop
6:40 am - 3:10 pmMDW-YWG
8h 30m1 stop
Tue, Jan 14 - Fri, Jan 24
7:30 am - 4:14 pmYWG-MDW
8h 44m1 stop
6:15 am - 3:10 pmMDW-YWG
8h 55m1 stop
Tue, Jan 7 - Mon, Jan 13
7:30 am - 5:53 pmYWG-MDW
10h 23m1 stop
6:40 am - 3:10 pmMDW-YWG
8h 30m1 stop
Fri, Jan 24 - Fri, Jan 31
7:30 am - 5:12 pmYWG-MDW
9h 42m1 stop
11:25 am - 9:09 pmMDW-YWG
9h 44m2 stops
Fri, Dec 6 - Thu, Dec 12
6:55 am - 6:14 pmYWG-MDW
11h 19m2 stops
6:59 pm - 11:42 pmMDW-YWG
4h 43m1 stop
$427Delta
Find Deal
Tue, Jan 14 - Tue, Jan 21
6:55 am - 12:46 pmYWG-MDW
5h 51m1 stop
10:19 am - 4:47 pmMDW-YWG
6h 28m1 stop
$428Delta
Find Deal
Fri, Jan 10 - Tue, Jan 14
5:37 pm - 12:46 pmYWG-MDW
19h 09m1 stop
10:19 am - 4:47 pmMDW-YWG
6h 28m1 stop
$484WestJet
Find Deal
Tue, Jan 7 - Wed, Jan 15
5:37 pm - 5:47 pmYWG-MDW
24h 10m1 stop
9:34 am - 12:35 amMDW-YWG
15h 01m2 stops
$485WestJet
Find Deal
Wed, Jan 8 - Wed, Jan 15
7:00 pm - 11:10 amYWG-MDW
16h 10m1 stop
12:05 pm - 11:40 pmMDW-YWG
11h 35m1 stop
$514Porter Airlines
Find Deal
Thu, Dec 19 - Mon, Dec 23
11:35 am - 12:00 pmYWG-MDW
24h 25m2 stops
11:15 am - 6:04 pmMDW-YWG
30h 49m2 stops
$541Porter Airlines
Find Deal
Fri, Dec 13 - Tue, Dec 17
7:30 am - 5:50 pmYWG-MDW
10h 20m1 stop
Fri, Jan 10
7:30 am - 5:50 pmYWG-MDW
10h 20m1 stop
Fri, Jan 10
7:30 am - 11:42 amYWG-MDW
28h 12m1 stop
Mon, Dec 9
5:00 am - 4:40 pmYWG-MDW
11h 40m1 stop
$223Porter Airlines
Find Deal
Sun, Dec 8
6:55 am - 6:14 pmYWG-MDW
11h 19m2 stops
$241Delta
Find Deal
Fri, Jan 10
11:35 am - 3:01 pmYWG-MDW
27h 26m3 stops
Wed, Nov 27
12:20 pm - 11:21 pmYWG-MDW
11h 01m2 stops
Mon, Dec 9
6:45 pm - 4:40 pmYWG-MDW
21h 55m1 stop
$292Porter Airlines
Find Deal
Sun, Dec 8
12:20 pm - 10:12 amYWG-MDW
21h 52m2 stops
$325WestJet
Find Deal
Fri, Jan 10
12:20 pm - 9:50 amYWG-MDW
21h 30m2 stops
$355WestJet
Find Deal
Sun, Dec 8

Delta flights from Winnipeg to Chicago Midway Airport

Our best Delta deals on Winnipeg to Chicago Midway Airport flight tickets
Delta
Jan 14
YWG6:55 amWinnipeg
11h 19m
2 stops
MDW6:14 pmChicago Midway
Jan 21
MDW6:59 pmChicago Midway
4h 43m
1 stop
YWG11:42 pmWinnipeg
Delta
Jan 10
YWG6:55 amWinnipeg
5h 51m
1 stop
MDW12:46 pmChicago Midway
Jan 14
MDW10:19 amChicago Midway
6h 28m
1 stop
YWG4:47 pmWinnipeg
Delta
Jan 12
YWG6:55 amWinnipeg
5h 51m
1 stop
MDW12:46 pmChicago Midway
Jan 20
MDW10:19 amChicago Midway
6h 28m
1 stop
YWG4:47 pmWinnipeg

Porter Airlines flights from Winnipeg to Chicago Midway Airport

Our best Porter Airlines deals on Winnipeg to Chicago Midway Airport flight tickets
Porter Airlines
Dec 19
YWG7:00 pmWinnipeg
16h 10m
1 stop
MDW11:10 amChicago Midway
Dec 23
MDW12:05 pmChicago Midway
11h 35m
1 stop
YWG11:40 pmWinnipeg
Porter Airlines
Dec 13
YWG11:35 amWinnipeg
24h 25m
2 stops
MDW12:00 pmChicago Midway
Dec 17
MDW11:15 amChicago Midway
30h 49m
2 stops
YWG6:04 pmWinnipeg
Porter Airlines
Dec 6
YWG6:45 pmWinnipeg
17h 15m
1 stop
MDW12:00 pmChicago Midway
Dec 9
MDW5:35 pmChicago Midway
17h 10m
1 stop
YWG10:45 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 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

Best Price Found

$141

Fastest flight time

4h 13m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Winnipeg in the past 72 hours is $141. The best round-trip flight deal from Winnipeg to Chicago Midway Airport found on momondo in the last 72 hours is $247.
The fastest flight from Winnipeg to Chicago Midway Airport takes 4h 13m
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 13m.

  • 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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