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Cheap flights from Chicago Midway Airport to Winnipeg from $189

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 12/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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
12:45 pm - 5:47 pmYWG-MDW
5h 02m1 stop
Fri, Jan 17 - Sun, Jan 19
9:38 am - 10:45 amMDW-YWG
25h 07m2 stops
7:00 pm - 1:31 pmYWG-MDW
18h 31m2 stops
Thu, Dec 12 - Mon, Dec 16
12:05 pm - 9:09 pmMDW-YWG
9h 04m2 stops
11:35 am - 10:20 amYWG-MDW
22h 45m2 stops
$530Porter Airlines
Find Deal
Fri, Dec 13 - Mon, Dec 16
9:38 am - 10:45 amMDW-YWG
25h 07m3 stops
7:00 pm - 1:31 pmYWG-MDW
18h 31m2 stops
Thu, Dec 12 - Mon, Dec 16
5:35 pm - 6:04 pmMDW-YWG
24h 29m2 stops
5:37 pm - 12:46 pmYWG-MDW
19h 09m1 stop
Mon, Dec 16 - Mon, Jan 6
10:19 am - 4:47 pmMDW-YWG
6h 28m1 stop
12:45 pm - 5:47 pmYWG-MDW
5h 02m1 stop
$544Delta
Find Deal
Tue, Jan 14 - Sun, Jan 19
6:00 am - 4:47 pmMDW-YWG
10h 47m2 stops
12:45 pm - 5:47 pmYWG-MDW
5h 02m1 stop
$554Delta
Find Deal
Tue, Jan 14 - Sun, Jan 19
9:38 am - 11:45 amMDW-YWG
26h 07m1 stop
6:55 am - 5:47 pmYWG-MDW
10h 52m1 stop
$575WestJet
Find Deal
Mon, Dec 16 - Mon, Jan 6
2:15 pm - 11:45 amMDW-YWG
21h 30m1 stop
5:00 am - 6:14 pmYWG-MDW
13h 14m2 stops
$579WestJet
Find Deal
Mon, Dec 16 - Mon, Jan 6
5:35 pm - 5:50 pmMDW-YWG
24h 15m1 stop
11:35 am - 12:00 pmYWG-MDW
24h 25m2 stops
$596Porter Airlines
Find Deal
Mon, Dec 9 - Fri, Dec 13
12:05 pm - 11:40 pmMDW-YWG
11h 35m1 stop
$189Porter Airlines
Find Deal
Wed, Dec 18
12:05 pm - 11:40 pmMDW-YWG
11h 35m1 stop
$190Porter Airlines
Find Deal
Wed, Dec 18
6:59 pm - 11:40 pmMDW-YWG
28h 41m2 stops
Sat, Jan 11
5:35 pm - 6:04 pmMDW-YWG
24h 29m2 stops
$271Porter Airlines
Find Deal
Wed, Dec 18
6:59 pm - 11:42 pmMDW-YWG
4h 43m1 stop
$278Delta
Find Deal
Sat, Jan 11
11:19 am - 3:35 pmMDW-YWG
28h 16m3 stops
$315WestJet
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
Dec 13
MDW12:05 pmChicago Midway
9h 04m
2 stops
YWG9:09 pmWinnipeg
Dec 16
YWG11:35 amWinnipeg
22h 45m
2 stops
MDW10:20 amChicago Midway
Porter Airlines
Dec 9
MDW5:35 pmChicago Midway
24h 15m
1 stop
YWG5:50 pmWinnipeg
Dec 13
YWG11:35 amWinnipeg
24h 25m
2 stops
MDW12:00 pmChicago Midway
Porter Airlines
Dec 9
MDW12:05 pmChicago Midway
22h 40m
1 stop
YWG10:45 amWinnipeg
Dec 13
YWG6:45 pmWinnipeg
17h 15m
1 stop
MDW12:00 pmChicago Midway

Delta flights from Chicago Midway Airport to Winnipeg

Our best Delta deals on Chicago Midway Airport to Winnipeg flight tickets
Delta
Jan 14
MDW10:19 amChicago Midway
6h 28m
1 stop
YWG4:47 pmWinnipeg
Jan 19
YWG12:45 pmWinnipeg
5h 02m
1 stop
MDW5:47 pmChicago Midway
Delta
Jan 14
MDW6:00 amChicago Midway
10h 47m
2 stops
YWG4:47 pmWinnipeg
Jan 19
YWG12:45 pmWinnipeg
5h 02m
1 stop
MDW5:47 pmChicago Midway
Delta
Jan 11
MDW6:59 pmChicago Midway
4h 43m
1 stop
YWG11:42 pmWinnipeg
Jan 26
YWG6:55 amWinnipeg
5h 51m
1 stop
MDW12:46 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, March 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 $211. If you’re not able to fly to Winnipeg in March, then September is your next best option. Flight prices from Chicago Midway Airport to Winnipeg during September average around $431.

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 $456. 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 $749.

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 $554. 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.

How far in advance should I book a flight to Winnipeg?

Most flyers found that booking tickets 46 days in advance of their planned departure date is the best time to get cheap flights to Winnipeg. During this timeframe, flight prices are around $537. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Winnipeg from Chicago Midway Airport for as low as $131 on momondo.

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

You could potentially save up to 22% 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

$189

Fastest flight time

4h 20m

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 $189. The best round-trip flight deal from Chicago Midway Airport to Winnipeg found on momondo in the last 72 hours is $451.
The fastest flight from Chicago Midway Airport to Winnipeg takes 4h 20m
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 20m 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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