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Cheap flights from Winnipeg (YWG) to Midway (MDW) from $180

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
YWG — MDW
May 21 — May 281
From?
To?
Tue 5/21
Tue 5/28
1 adult, Economy
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Cheap flight deals from Winnipeg to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 16, 2024.

Round-trip from

$223
From Winnipeg to Chicago Midway
Search Deals

How far in advance should I book a flight from Winnipeg to Chicago Midway Airport?

Users have found that booking a flight from Winnipeg to Chicago Midway Airport at least 17 days early can save you up to 115% on average compared to booking a flight this week. If booking 17 days before your flight isn’t an option for you, users have found flights from Winnipeg to Chicago Midway Airport for as little as $545 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $763 for flights departing within the next 3 days.

What is the cheapest month to fly from Winnipeg to Chicago Midway Airport?

Flights from Winnipeg to Chicago Midway Airport lean towards being more expensive in August. Prices are generally better when you fly from Winnipeg to Chicago Midway Airport in November, with the cheapest ticket starting at $272.

When is the cheapest time to fly from Winnipeg to Chicago Midway Airport (YWG - MDW)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Chicago Midway Airport as you normally would.

Cheap WestJet flights from Winnipeg to Midway

Explore cheap flight options specifically provided by WestJet for the route between Winnipeg and Midway. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Peruse some of the lowest-priced WestJet flights we've found from Winnipeg to Chicago. Deals update often to give you more flight options matching your criteria
Sat 6/156:55 amYWG - MDW
1 stop11h 35mWestJet
Wed 6/196:00 amMDW - YWG
1 stop9h 22mWestJet
Deal found 5/16$324
Mon 6/36:55 amYWG - MDW
1 stop11h 12mWestJet
Tue 6/119:29 amMDW - YWG
1 stop14h 00mWestJet
Deal found 5/15$326
Mon 6/36:30 amYWG - MDW
2 stops11h 37mWestJet
Tue 6/119:29 amMDW - YWG
1 stop14h 00mWestJet
Deal found 5/15$331
Sat 5/257:30 amYWG - MDW
2 stops27h 32mWestJet
Wed 5/294:41 pmMDW - YWG
1 stop22h 44mWestJet
Deal found 5/14$333
Sat 6/156:55 amYWG - MDW
1 stop11h 35mWestJet
Wed 6/196:00 amMDW - YWG
2 stops15h 12mWestJet
Deal found 5/16$334
Sat 6/157:30 amYWG - MDW
2 stops25h 18mWestJet
Wed 6/199:34 amMDW - YWG
2 stops11h 38mWestJet
Deal found 5/16$340
Mon 6/37:30 amYWG - MDW
2 stops14h 31mWestJet
Tue 6/119:29 amMDW - YWG
2 stops28h 10mWestJet
Deal found 5/15$371
Sat 5/257:30 amYWG - MDW
2 stops27h 32mWestJet
Wed 5/295:47 pmMDW - YWG
2 stops30h 10mWestJet
Deal found 5/14$375
Tue 6/46:30 amYWG - MDW
2 stops11h 37mWestJet
Sat 6/812:07 pmMDW - YWG
1 stop11h 22mWestJet
Deal found 5/15$381

Cheap Delta flights from Winnipeg to Midway

Explore cheap flight options specifically provided by Delta for the route between Winnipeg and Midway. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Browse through some of the cheapest Delta flights traveling from Winnipeg to Chicago. Deals are refreshing constantly so come back soon for more options.
Sat 5/256:55 amYWG - MDW
1 stop4h 07mDelta
Wed 5/297:10 pmMDW - YWG
1 stop4h 13mDelta
Deal found 5/15$390
Wed 9/186:55 amYWG - MDW
1 stop6h 07mDelta
Tue 9/246:45 pmMDW - YWG
1 stop4h 36mDelta
Deal found 5/15$403
Thu 6/137:30 amYWG - MDW
2 stops9h 34mDelta
Thu 6/209:34 amMDW - YWG
2 stops13h 55mDelta
Deal found 5/16$407
Wed 5/226:55 amYWG - MDW
2 stops5h 45mDelta
Mon 5/278:45 amMDW - YWG
2 stops14h 38mDelta
Deal found 5/15$412
Mon 8/56:55 amYWG - MDW
1 stop6h 14mDelta
Sat 8/105:00 pmMDW - YWG
1 stop6h 21mDelta
Deal found 5/16$448
Sun 9/88:00 amYWG - MDW
1 stop9h 59mDelta
Fri 9/136:45 pmMDW - YWG
1 stop4h 36mDelta
Deal found 5/16$520
Thu 5/306:55 amYWG - MDW
2 stops10h 11mDelta
Sun 6/29:32 amMDW - YWG
2 stops11h 40mDelta
Deal found 5/15$841

Cheap Winnipeg to Midway flights in May & June 2024

Find cheap flight options from Winnipeg to Midway specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,637,452 searches. Prices were last updated on May 16, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. If these deals don't appeal to you, be sure to come back soon for more options.
Mon 6/36:55 amYWG - MDW
1 stop11h 12mWestJet
Tue 6/119:29 amMDW - YWG
1 stop14h 00mWestJet
Deal found 5/15$326
Mon 6/36:30 amYWG - MDW
2 stops11h 37mWestJet
Tue 6/119:29 amMDW - YWG
1 stop14h 00mWestJet
Deal found 5/15$331
Sat 5/257:30 amYWG - MDW
2 stops27h 32mWestJet
Wed 5/294:41 pmMDW - YWG
1 stop22h 44mWestJet
Deal found 5/14$333
Sat 5/257:30 amYWG - MDW
2 stops25h 21mWestJet
Wed 5/2912:42 pmMDW - YWG
1 stop26h 43mWestJet
Deal found 5/15$334
Sat 5/257:30 amYWG - MDW
2 stops8h 43mWestJet
Wed 5/299:46 amMDW - YWG
2 stops14h 11mWestJet
Deal found 5/15$340
Mon 6/37:30 amYWG - MDW
2 stops14h 31mWestJet
Tue 6/119:29 amMDW - YWG
2 stops28h 10mWestJet
Deal found 5/15$371
Sat 5/257:30 amYWG - MDW
2 stops27h 32mWestJet
Wed 5/295:47 pmMDW - YWG
2 stops30h 10mWestJet
Deal found 5/14$375
Tue 6/46:30 amYWG - MDW
2 stops11h 37mWestJet
Sat 6/812:07 pmMDW - YWG
1 stop11h 22mWestJet
Deal found 5/15$381
Sat 5/256:55 amYWG - MDW
1 stop4h 07mDelta
Wed 5/297:10 pmMDW - YWG
1 stop4h 13mDelta
Deal found 5/15$390

Winnipeg to Midway 2024 flight deals

Discover exclusive flight deals for travel between Winnipeg and Midway in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. If these deals don't appeal to you, be sure to come back soon for more options.
Mon 6/36:55 amYWG - MDW
1 stop11h 12mWestJet
Tue 6/119:29 amMDW - YWG
1 stop14h 00mWestJet
Deal found 5/15$326
Mon 6/36:30 amYWG - MDW
2 stops11h 37mWestJet
Tue 6/119:29 amMDW - YWG
1 stop14h 00mWestJet
Deal found 5/15$331
Sat 5/257:30 amYWG - MDW
2 stops27h 32mWestJet
Wed 5/294:41 pmMDW - YWG
1 stop22h 44mWestJet
Deal found 5/14$333
Sat 5/257:30 amYWG - MDW
2 stops25h 21mWestJet
Wed 5/2912:42 pmMDW - YWG
1 stop26h 43mWestJet
Deal found 5/15$334
Sat 5/257:30 amYWG - MDW
2 stops8h 43mWestJet
Wed 5/299:46 amMDW - YWG
2 stops14h 11mWestJet
Deal found 5/15$340
Mon 6/37:30 amYWG - MDW
2 stops14h 31mWestJet
Tue 6/119:29 amMDW - YWG
2 stops28h 10mWestJet
Deal found 5/15$371
Sat 5/257:30 amYWG - MDW
2 stops27h 32mWestJet
Wed 5/295:47 pmMDW - YWG
2 stops30h 10mWestJet
Deal found 5/14$375
Tue 6/46:30 amYWG - MDW
2 stops11h 37mWestJet
Sat 6/812:07 pmMDW - YWG
1 stop11h 22mWestJet
Deal found 5/15$381
Sat 5/256:55 amYWG - MDW
1 stop4h 07mDelta
Wed 5/297:10 pmMDW - YWG
1 stop4h 13mDelta
Deal found 5/15$390

Winnipeg to Midway flights leaving soon

Find last-minute flight options from Winnipeg to Midway for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Have a look at some of the flights available from Winnipeg to Chicago departing last-minute. It's wise to confirm all flight details are correct before booking.
Sat 5/257:30 amYWG - MDW
2 stops27h 32mWestJet
Wed 5/294:41 pmMDW - YWG
1 stop22h 44mWestJet
Deal found 5/14$333
Sat 5/257:30 amYWG - MDW
2 stops25h 21mWestJet
Wed 5/2912:42 pmMDW - YWG
1 stop26h 43mWestJet
Deal found 5/15$334
Sat 5/257:30 amYWG - MDW
2 stops8h 43mWestJet
Wed 5/299:46 amMDW - YWG
2 stops14h 11mWestJet
Deal found 5/15$340
Sat 5/257:30 amYWG - MDW
2 stops27h 32mWestJet
Wed 5/295:47 pmMDW - YWG
2 stops30h 10mWestJet
Deal found 5/14$375
Sat 5/256:55 amYWG - MDW
1 stop10h 00mWestJet
Wed 5/299:46 amMDW - YWG
1 stop13h 37mWestJet
Deal found 5/14$381
Sat 5/256:55 amYWG - MDW
1 stop4h 07mDelta
Wed 5/297:10 pmMDW - YWG
1 stop4h 13mDelta
Deal found 5/15$390
Wed 5/228:00 amYWG - MDW
1 stop6h 41mMultiple Airlines
Mon 5/277:53 amMDW - YWG
1 stop7h 32mMultiple Airlines
Deal found 5/15$399
Wed 5/226:55 amYWG - MDW
2 stops5h 45mDelta
Mon 5/278:45 amMDW - YWG
2 stops14h 38mDelta
Deal found 5/15$412
Wed 5/227:30 amYWG - MDW
2 stops9h 36mMultiple Airlines
Mon 5/277:53 amMDW - YWG
1 stop7h 32mMultiple Airlines
Deal found 5/15$442

One-way flights to Midway from Winnipeg

Search for one-way flight options from Winnipeg to Midway. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Take a look at some of the one-way flights we've detected from Winnipeg to Chicago. Users needing a return flight from Winnipeg to Chicago should utilize the search form above.
Thu 7/48:00 amYWG - MDW
1 stop9h 01mMultiple Airlines
Deal found 5/15$180
Fri 9/138:00 amYWG - MDW
1 stop12h 49mMultiple Airlines
Deal found 5/16$185
Thu 7/46:55 amYWG - MDW
2 stops14h 51mDelta
Deal found 5/15$186
Thu 7/46:30 amYWG - MDW
2 stops12h 01mWestJet
Deal found 5/15$193
Thu 7/48:00 amYWG - MDW
1 stop9h 01mMultiple Airlines
Deal found 5/15$198
Tue 8/276:50 amYWG - MDW
2 stops10h 13mWestJet
Deal found 5/16$200
Fri 7/56:55 amYWG - MDW
1 stop11h 36mWestJet
Deal found 5/15$204
Fri 7/56:55 amYWG - MDW
1 stop4h 33mDelta
Deal found 5/15$222
Wed 7/36:55 amYWG - MDW
2 stops10h 10mDelta
Deal found 5/15$228

Find flights from Winnipeg to Midway within your budget

Customize your flight search to find flights from Winnipeg to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$324 - $528

Route

Depart

Return

Price

WinnipegChicago Midway

YWG - MDW

YWGMDW

Winnipeg

Sat 6/15

1 stop11h 35m

Chicago Midway

Wed 6/19

1 stop9h 22m

$324

WinnipegChicago Midway

YWG - MDW

YWGMDW

Winnipeg

Mon 6/3

1 stop11h 12m

Chicago Midway

Tue 6/11

1 stop14h 00m

$326

WinnipegChicago Midway

YWG - MDW

YWGMDW

Winnipeg

Mon 6/3

2 stops11h 37m

Chicago Midway

Tue 6/11

1 stop14h 00m

$331

WinnipegChicago Midway

YWG - MDW

YWGMDW

Winnipeg

Sat 6/15

1 stop11h 35m

Chicago Midway

Wed 6/19

2 stops15h 12m

$334

WinnipegChicago Midway

YWG - MDW

YWGMDW

Winnipeg

Sat 6/15

2 stops25h 18m

Chicago Midway

Wed 6/19

2 stops11h 38m

$340

WinnipegChicago Midway

YWG - MDW

YWGMDW

Winnipeg

Wed 9/18

1 stop6h 07m

Chicago Midway

Tue 9/24

1 stop4h 36m

$403

WinnipegChicago Midway

YWG - MDW

YWGMDW

Winnipeg

Thu 6/13

2 stops9h 34m

Chicago Midway

Thu 6/20

2 stops13h 55m

$407

WinnipegChicago Midway

YWG - MDW

YWGMDW

Winnipeg

Thu 6/13

1 stop15h 37m

Chicago Midway

Thu 6/20

1 stop14h 20m

$469

WinnipegChicago Midway

YWG - MDW

YWGMDW

Winnipeg

Fri 6/14

3 stops30h 40m

Chicago Midway

Fri 6/21

2 stops10h 07m

$528

Flights are sorted by cheapest first

Deals found on 5/16

No data available for this route at this time. Please check back soon.

Average price of flights to Midway by month

Plan your trip from Winnipeg to Midway by taking into account the cheapest months to travel. The average price of a one-way flight from Winnipeg to Midway is currently $200 while a round-trip flight costs $385. Price data was last updated on May 12, 2024.

Currently, December is the cheapest month in which you can book a flight from Winnipeg to Chicago Midway Airport (average of $140). Flying from Winnipeg to Chicago Midway Airport in July is currently the most expensive (average of $250). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

January

$194

February

$190

March

$219

April

$159

May

$183

June

$216

July

$250

August

$196

September

$155

October

$143

November

$166

December

$140

Temperature and rainfall in Midway by month

Plan your trip to Midway by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

23 - 73.4 °F

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated May 16, 2024.
See what other customers who have flown with WestJet, Delta and Porter Airlines from Winnipeg to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Food

7.4

Comfort

7.9

Entertainment

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Delta
8.0
Very good
10,673 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Food

7.4

Comfort

7.9

Entertainment

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

WestJet
7.5
Good
2,919 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Food

7.4

Comfort

7.9

Entertainment

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Porter Airlines
7.4
Good
415 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Food

7.4

Comfort

7.9

Entertainment

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Winnipeg to Chicago Midway?

    Most people fly from Winnipeg (YWG) if they book a flight from Winnipeg to Chicago Midway. On average, Winnipeg has 0 outbound flights to Chicago Midway per day from 0 airlines. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

  • Can I find flights from Winnipeg to Chicago Midway Airport for under $400 on Cheapflights?

    Yes, there are multiple flights from Winnipeg to Chicago Midway Airport for under $400. The cheapest flight booked recently is on WestJet for just $324, but on average you can expect to pay $394.

  • Are there last-minute flights available from Winnipeg to Chicago Midway Airport for under $400?

    There are currently 10+ open flights from Winnipeg to Chicago Midway Airport within the next 7 days for less than $400.

  • What are the cheapest airlines flying from Winnipeg to Chicago Midway Airport round-trip?

    WestJet, at $324, was found to be the cheapest airline from Winnipeg to Chicago Midway Airport.Alternate airlines to your destination round-trip include Delta and Porter Airlines.

  • What are the cheapest airlines to fly from Winnipeg to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $186 on Delta. Other airlines that offer cheap prices include WestJet from $193 and Porter Airlines from $258 one-way.

  • What does YWG to MDW mean?

    This is defined as Winnipeg Airport (YWG) and Chicago Midway Airport (MDW). Codes like Chicago Midway Airport are often used to just call airports uniquely.

  • Can I find deals for flights from Winnipeg to Midway that include extra baggage allowance?

    The amount of baggage you can bring on your Winnipeg to Midway flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Winnipeg to Midway with specific airlines?

    Yes, Cheapflights allows you to browse and filter Winnipeg to Midway flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Winnipeg to Midway that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Midway.

  • Can I find deals for business class flights from Winnipeg to Midway?

    Yes. Cheapflights offers flight deals from Winnipeg to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Winnipeg to Midway that allow pets onboard?

    Many airlines flying from Winnipeg to Midway offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Winnipeg to Midway?

    Yes, you can often find last-minute deals on Winnipeg to Midway flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Winnipeg to Chicago Midway Airport flight deals updated?

    The Winnipeg to Chicago Midway Airport flight deals you see on this page were last updated on 5/15.

See more FAQs

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Search flights from Winnipeg to Midway by cabin class

Find flights from Winnipeg to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Winnipeg to Midway?

Cheapflights makes it easy to find Winnipeg to Midway flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Midway?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Winnipeg to Midway.

Can Cheapflights find flights from Winnipeg to Midway with no change fees?

Yes, we can. To see specific flights from Winnipeg to Midway with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Winnipeg to Midway become cheaper?

Of course! You can now track prices for flights from Winnipeg to Midway and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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