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Cheap flights from Chicago Midway Airport to Winnipeg from $102

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 1/13. 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 Chicago Midway Airport to Winnipeg

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago Midway Airport to Winnipeg 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 Chicago Midway Airport to Winnipeg.

Cheap last minute flights

Planning a quick getaway from Chicago Midway Airport to Winnipeg? 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 Winnipeg, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago Midway Airport to Winnipeg

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

All round-trip flight deals to Winnipeg

The cheapest plane tickets to Winnipeg found on KAYAK recently.
6:40 am - 3:10 pmMDW-YWG
8h 30m1 stop
7:30 am - 4:16 pmYWG-MDW
8h 46m1 stop
Fri, Jan 17 - Tue, Jan 28
1:05 pm - 12:35 amMDW-YWG
11h 30m1 stop
8:00 pm - 12:10 pmYWG-MDW
16h 10m1 stop
Wed, Jan 15 - Wed, Jan 22
1:05 pm - 12:35 amMDW-YWG
11h 30m1 stop
8:00 pm - 12:10 pmYWG-MDW
16h 10m1 stop
Thu, Jan 16 - Sun, Jan 19
1:05 pm - 12:35 amMDW-YWG
11h 30m1 stop
5:15 pm - 12:10 pmYWG-MDW
18h 55m2 stops
Wed, Jan 15 - Wed, Jan 22
10:19 am - 11:25 amMDW-YWG
25h 06m3 stops
8:00 pm - 10:36 amYWG-MDW
14h 36m2 stops
$476WestJet
Find Deal
Tue, Jan 21 - Fri, Jan 24
1:26 pm - 11:51 amMDW-YWG
22h 25m1 stop
6:00 am - 5:43 pmYWG-MDW
11h 43m2 stops
$533WestJet
Find Deal
Mon, Feb 24 - Wed, Feb 26
10:19 am - 4:47 pmMDW-YWG
6h 28m1 stop
6:55 am - 6:14 pmYWG-MDW
11h 19m2 stops
$575Delta
Find Deal
Fri, Jan 17 - Tue, Jan 28
10:19 am - 4:43 pmMDW-YWG
6h 24m1 stop
12:45 pm - 5:43 pmYWG-MDW
4h 58m1 stop
$598Delta
Find Deal
Mon, Feb 24 - Wed, Feb 26
1:05 pm - 6:04 pmMDW-YWG
28h 59m2 stops
11:35 am - 12:10 pmYWG-MDW
24h 35m2 stops
$737Porter Airlines
Find Deal
Sat, Jan 11 - Sun, Jan 19
1:05 pm - 6:04 pmMDW-YWG
28h 59m2 stops
11:35 am - 12:10 pmYWG-MDW
24h 35m2 stops
$745Porter Airlines
Find Deal
Sat, Feb 1 - Sat, Feb 8
6:15 am - 3:10 pmMDW-YWG
8h 55m1 stop
Mon, Jan 13
7:32 pm - 3:10 pmMDW-YWG
19h 38m1 stop
Thu, Jan 9
7:15 am - 10:32 pmMDW-YWG
15h 17m3 stops
Thu, Jan 9
7:30 am - 11:40 pmMDW-YWG
16h 10m2 stops
Thu, Jan 9
12:44 pm - 3:10 pmMDW-YWG
26h 26m1 stop
$299WestJet
Find Deal
Thu, Jan 23
1:05 pm - 6:04 pmMDW-YWG
28h 59m2 stops
$302Porter Airlines
Find Deal
Sun, Jan 12
1:05 pm - 6:04 pmMDW-YWG
28h 59m2 stops
$314Porter Airlines
Find Deal
Thu, Jan 23
11:19 am - 11:42 pmMDW-YWG
12h 23m1 stop
$317WestJet
Find Deal
Sat, Jan 11
2:08 pm - 12:35 amMDW-YWG
10h 27m2 stops
$328WestJet
Find Deal
Mon, Jan 13
5:05 pm - 12:35 amMDW-YWG
31h 30m2 stops
$375WestJet
Find Deal
Sat, Jan 11

Porter Airlines flights from Chicago Midway Airport to Winnipeg

Our best Porter Airlines deals on Chicago Midway Airport to Winnipeg flight tickets
Porter Airlines
Jan 11
MDW1:05 pmChicago Midway
28h 59m
2 stops
YWG6:04 pmWinnipeg
Jan 19
YWG11:35 amWinnipeg
24h 35m
2 stops
MDW12:10 pmChicago Midway
Porter Airlines
Feb 1
MDW1:05 pmChicago Midway
28h 59m
2 stops
YWG6:04 pmWinnipeg
Feb 8
YWG11:35 amWinnipeg
24h 35m
2 stops
MDW12:10 pmChicago Midway
Porter Airlines
Dec 26
MDW11:25 amChicago Midway
23h 20m
1 stop
YWG10:45 amWinnipeg
Jan 8
YWG7:00 pmWinnipeg
17h 10m
1 stop
MDW12:10 pmChicago Midway

WestJet flights from Chicago Midway Airport to Winnipeg

Our best WestJet deals on Chicago Midway Airport to Winnipeg flight tickets
WestJet
Jan 21
MDW10:19 amChicago Midway
25h 06m
3 stops
YWG11:25 amWinnipeg
Jan 24
YWG8:00 pmWinnipeg
14h 36m
2 stops
MDW10:36 amChicago Midway
WestJet
Feb 24
MDW1:26 pmChicago Midway
22h 25m
1 stop
YWG11:51 amWinnipeg
Feb 26
YWG6:00 amWinnipeg
11h 43m
2 stops
MDW5:43 pmChicago Midway
WestJet
Jan 8
MDW1:26 pmChicago Midway
10h 16m
1 stop
YWG11:42 pmWinnipeg
Jan 14
YWG6:55 amWinnipeg
10h 52m
1 stop
MDW5:47 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 month to fly to Winnipeg?

In general, September is the cheapest month to fly from Chicago Midway Airport to Winnipeg. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $431. If you’re not able to fly to Winnipeg in September, then May is your next best option. Flight prices from Chicago Midway Airport to Winnipeg during May average around $462.

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 Thursday when prices can be found for as low as $427. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday 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 $683.

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 morning when flights can be purchased for as low as $551. 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.

Can stopping save me money on Chicago Midway Airport to Winnipeg flights?

You could potentially save up to 49% on your flight if you consider stops on a Chicago Midway Airport to Winnipeg flight.

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

$102

Fastest flight time

4h 43m

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 $102. The best round-trip flight deal from Chicago Midway Airport to Winnipeg found on momondo in the last 72 hours is $252.
The fastest flight from Chicago Midway Airport to Winnipeg takes 4h 43m
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 4h 43m 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.


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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