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Cheap flights from Chicago Midway Airport to Winnipeg from $240

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Winnipeg departing on 5/17. 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 Chicago Midway Airport to Winnipeg

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago Midway Airport to Winnipeg.
 Logo
6:40 am - 4:28 pmMDW-YWG
9h 48m1 stop
 Logo
8:30 am - 11:22 pmYWG-MDW
14h 52m2 stops
Wed, Jun 4 - Sat, Jun 7
 Logo
6:00 am - 4:28 pmMDW-YWG
10h 28m1 stop
 Logo
6:30 am - 8:53 pmYWG-MDW
14h 23m2 stops
Thu, Jun 19 - Sun, Jun 22
 Logo
6:00 am - 4:28 pmMDW-YWG
10h 28m1 stop
 Logo
6:30 am - 5:12 pmYWG-MDW
10h 42m2 stops
Wed, Jun 11 - Sat, Jun 14
 Logo
6:40 am - 4:28 pmMDW-YWG
9h 48m1 stop
 Logo
12:52 pm - 5:47 pmYWG-MDW
4h 55m1 stop
Wed, Jun 4 - Sat, Jun 7
Porter Airlines Logo
5:20 pm - 10:26 amMDW-YWG
17h 06m2 stops
Porter Airlines Logo
11:25 am - 8:45 amYWG-MDW
21h 20m2 stops
$412Porter Airlines
Find Deal
Thu, May 8 - Mon, May 12
 Logo
5:20 pm - 9:43 amMDW-YWG
16h 23m1 stop
 Logo
6:55 pm - 8:19 amYWG-MDW
13h 24m1 stop
Thu, Jun 19 - Sun, Jun 22
Porter Airlines Logo
9:40 am - 10:46 pmMDW-YWG
13h 06m2 stops
Porter Airlines Logo
6:55 pm - 8:45 amYWG-MDW
13h 50m1 stop
$418Porter Airlines
Find Deal
Thu, Jun 12 - Sun, Jun 15
Delta Logo
9:20 am - 4:45 pmMDW-YWG
7h 25m1 stop
Delta Logo
8:30 am - 1:15 pmYWG-MDW
4h 45m1 stop
$534Delta
Find Deal
Sat, May 17 - Sat, May 24
Delta Logo
1:08 pm - 11:25 pmMDW-YWG
10h 17m2 stops
Delta Logo
12:52 pm - 5:14 pmYWG-MDW
4h 22m1 stop
$535Delta
Find Deal
Sat, May 17 - Sat, May 24
WestJet Logo
1:55 pm - 8:08 pmMDW-YWG
6h 13m1 stop
WestJet Logo
9:00 am - 5:43 pmYWG-MDW
8h 43m1 stop
$941WestJet
Find Deal
Thu, May 8 - Mon, May 12

Porter Airlines flights from Chicago Midway Airport to Winnipeg

Our best Porter Airlines deals on Chicago Midway Airport to Winnipeg flight tickets
Porter Airlines
May 8
MDW5:20 pmChicago Midway
17h 06m
2 stops
YWG10:26 amWinnipeg
May 12
YWG11:25 amWinnipeg
21h 20m
2 stops
MDW8:45 amChicago Midway
Porter Airlines
Jun 12
MDW9:40 amChicago Midway
13h 06m
2 stops
YWG10:46 pmWinnipeg
Jun 15
YWG6:55 pmWinnipeg
13h 50m
1 stop
MDW8:45 amChicago Midway
Porter Airlines
Jun 18
MDW9:40 amChicago Midway
13h 06m
2 stops
YWG10:46 pmWinnipeg
Jun 21
YWG11:45 amWinnipeg
21h 00m
2 stops
MDW8:45 amChicago Midway

Delta flights from Chicago Midway Airport to Winnipeg

Our best Delta deals on Chicago Midway Airport to Winnipeg flight tickets
Delta
May 17
MDW9:20 amChicago Midway
7h 25m
1 stop
YWG4:45 pmWinnipeg
May 24
YWG8:30 amWinnipeg
4h 45m
1 stop
MDW1:15 pmChicago Midway
Delta
May 17
MDW1:08 pmChicago Midway
10h 17m
2 stops
YWG11:25 pmWinnipeg
May 24
YWG12:52 pmWinnipeg
4h 22m
1 stop
MDW5:14 pmChicago Midway
Delta
May 17
MDW1:08 pmChicago Midway
10h 17m
2 stops
YWG11:25 pmWinnipeg
May 24
YWG8:30 amWinnipeg
10h 15m
2 stops
MDW6:45 pmChicago Midway

See travel insights to Winnipeg from

How to get the cheapest flight ticket from Chicago Midway Airport to Winnipeg

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 day to depart on your flight to Winnipeg?

The cheapest day to depart on your flight to Winnipeg is on a Saturday when prices can be found for as low as $562. This is often the case because there is less demand to fly during this day of the week. On the other hand, Wednesday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $673.

What is the cheapest time of day to depart on your flight to Winnipeg?

The cheapest time of day to fly to Winnipeg is in the evening when flights can be purchased for as low as $594. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are $670 on average. Flights to Winnipeg from Chicago Midway Airport in the afternoon are generally more expensive because this time of day is more convenient for travelers’ schedules.

When to book flights from Chicago Midway Airport to Winnipeg

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Winnipeg according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Winnipeg (MDW to YWG) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Winnipeg

Best Price Found

$240

Fastest flight time

4h 55m

Direct flights

None

Airports in Winnipeg

1 airport
The best one-way flight to Winnipeg from Chicago Midway Airport in the past 72 hours is $240. The best round-trip flight deal from Chicago Midway Airport to Winnipeg found on momondo in the last 72 hours is $269.
The fastest flight from Chicago Midway Airport to Winnipeg takes 4h 55m
There are no direct flights from Chicago Midway Airport to Winnipeg. Popular non-direct route for this connection is Chicago Midway Airport - Winnipeg Airport.
There is 1 airport near Winnipeg: Winnipeg (YWG)

  • How far is Chicago Midway to Winnipeg by plane?

    Winnipeg is 717.8 mi away from Chicago Midway. Typically, this will take 6h 13m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to Winnipeg Airport?

    Prices for flights from Chicago Midway Airport to Winnipeg Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Chicago Midway Airport to Winnipeg Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Winnipeg Airport.

  • What documentation or ID do you need to fly to Winnipeg Airport?

    The travel and health documents you'll need for your trip to Winnipeg Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Winnipeg Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.


Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Scanterbury
Selkirk
Morden
Portage la Prairie

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Winnipeg?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Winnipeg. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Winnipeg with flexible booking policies on momondo?

All flight searches from Chicago to Winnipeg on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Winnipeg?

momondo provides multiple filters to help you find the best flight to Winnipeg from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Winnipeg right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Winnipeg 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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