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Cheap flights from Midway (MDW) to Winnipeg (YWG) from $131

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 5/29. 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.
MDW — YWG
May 8 — May 151
From?
To?
Wed 5/8
Wed 5/15
1 adult, Economy
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Cheap flight deals from Midway to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Winnipeg (YWG). 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 3, 2024.

Round-trip from

$388

One-way from

$182
From Chicago Midway to Winnipeg
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One-way flight from Chicago Midway to Winnipeg
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How far in advance should I book a flight from Chicago Midway Airport to Winnipeg?

Travelers have found it’s best to book a flight 8 days in advance to save up to 162% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 8 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago Midway Airport to Winnipeg 1-2 weeks in advance for as low as $337, or $1,274 for flights within the next 24 hours.

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

May is one of the best times of the year to fly to Winnipeg from Chicago Midway Airport. Prices for May average $590 per person but you can even find prices for as low as $207. The most expensive prices can be found in the month of December. Opting for a May flight can save you 52% on your journey compared to booking in December

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

When flying from Chicago Midway Airport to Winnipeg, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap WestJet flights from Midway to Winnipeg

Explore cheap flight options specifically provided by WestJet for the route between Midway and Winnipeg. 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 2,864,334 searches. Data last updated May 3, 2024.
Take a peek at the cheapest WestJet flights we've detected traveling from Chicago to Winnipeg. Make sure to double check the flight details before booking.
Wed 6/196:00 amMDW - YWG
1 stop9h 22mWestJet
Wed 8/218:00 amYWG - MDW
1 stop13h 47mWestJet
Deal found 5/2$381
Tue 6/49:46 amMDW - YWG
2 stops12h 54mWestJet
Fri 6/78:50 pmYWG - MDW
2 stops13h 01mWestJet
Deal found 5/2$416
Thu 5/302:15 pmMDW - YWG
1 stop9h 08mWestJet
Thu 6/65:35 pmYWG - MDW
1 stop25h 01mWestJet
Deal found 5/2$418
Tue 6/119:34 amMDW - YWG
2 stops28h 05mWestJet
Sat 6/156:50 amYWG - MDW
2 stops10h 14mWestJet
Deal found 5/2$434
Tue 6/49:46 amMDW - YWG
2 stops12h 54mWestJet
Fri 6/712:26 pmYWG - MDW
1 stop6h 10mWestJet
Deal found 5/2$442
Thu 5/303:45 pmMDW - YWG
1 stop23h 40mWestJet
Sun 6/28:00 amYWG - MDW
1 stop14h 01mWestJet
Deal found 5/2$449
Thu 5/309:32 amMDW - YWG
2 stops11h 40mWestJet
Sun 6/28:00 amYWG - MDW
1 stop14h 01mWestJet
Deal found 5/2$460
Tue 6/119:29 amMDW - YWG
2 stops13h 11mWestJet
Wed 6/127:30 amYWG - MDW
2 stops10h 29mWestJet
Deal found 5/2$494
Thu 5/309:46 amMDW - YWG
2 stops12h 57mWestJet
Thu 6/67:30 amYWG - MDW
2 stops9h 36mWestJet
Deal found 5/2$507

Cheap Delta flights from Midway to Winnipeg

Explore cheap flight options specifically provided by Delta for the route between Midway and Winnipeg. 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 2,864,334 searches. Data last updated May 3, 2024.
Browse through some of the cheapest Delta flights traveling from Chicago to Winnipeg. Deals are refreshing constantly so come back soon for more options.
Tue 6/112:24 pmMDW - YWG
1 stop9h 05mDelta
Sat 6/156:55 amYWG - MDW
2 stops10h 09mDelta
Deal found 5/2$394
Tue 6/112:24 pmMDW - YWG
1 stop9h 05mDelta
Thu 6/137:30 amYWG - MDW
2 stops9h 34mDelta
Deal found 5/2$491
Tue 6/119:34 amMDW - YWG
2 stops13h 55mDelta
Thu 6/137:30 amYWG - MDW
2 stops9h 34mDelta
Deal found 5/2$501
Tue 6/119:34 amMDW - YWG
2 stops11h 38mDelta
Thu 6/137:30 amYWG - MDW
2 stops9h 34mDelta
Deal found 5/2$502
Thu 5/309:32 amMDW - YWG
2 stops11h 40mDelta
Sun 6/26:55 amYWG - MDW
2 stops5h 45mDelta
Deal found 5/2$529
Fri 6/211:24 pmMDW - YWG
2 stops10h 05mDelta
Tue 6/256:55 amYWG - MDW
1 stop6h 49mDelta
Deal found 5/2$599
Tue 6/112:24 pmMDW - YWG
1 stop9h 05mDelta
Thu 6/136:55 amYWG - MDW
1 stop6h 49mDelta
Deal found 5/2$620
Fri 6/211:24 pmMDW - YWG
2 stops10h 05mDelta
Tue 6/256:55 amYWG - MDW
2 stops5h 48mDelta
Deal found 5/2$635
Fri 6/217:19 pmMDW - YWG
1 stop4h 10mDelta
Tue 6/256:55 amYWG - MDW
1 stop6h 49mDelta
Deal found 5/2$643

Cheap Midway to Winnipeg flights in May & June 2024

Find cheap flight options from Midway to Winnipeg specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,864,334 searches. Prices were last updated on May 3, 2024.
The lowest fares we've come across on flights traveling from Chicago to Winnipeg in May and June 2024. Check back soon for alternative fares.
Wed 6/196:00 amMDW - YWG
1 stop9h 22mWestJet
Wed 8/218:00 amYWG - MDW
1 stop13h 47mWestJet
Deal found 5/2$381
Tue 6/112:24 pmMDW - YWG
1 stop9h 05mDelta
Sat 6/156:55 amYWG - MDW
2 stops10h 09mDelta
Deal found 5/2$394
Tue 6/49:46 amMDW - YWG
2 stops12h 54mWestJet
Fri 6/78:50 pmYWG - MDW
2 stops13h 01mWestJet
Deal found 5/2$416
Thu 5/302:15 pmMDW - YWG
1 stop9h 08mWestJet
Thu 6/65:35 pmYWG - MDW
1 stop25h 01mWestJet
Deal found 5/2$418
Tue 6/119:34 amMDW - YWG
2 stops28h 05mWestJet
Sat 6/156:50 amYWG - MDW
2 stops10h 14mWestJet
Deal found 5/2$434
Tue 6/49:46 amMDW - YWG
2 stops12h 54mWestJet
Fri 6/712:26 pmYWG - MDW
1 stop6h 10mWestJet
Deal found 5/2$442
Thu 5/303:45 pmMDW - YWG
1 stop23h 40mWestJet
Sun 6/28:00 amYWG - MDW
1 stop14h 01mWestJet
Deal found 5/2$449
Thu 5/309:32 amMDW - YWG
2 stops11h 40mWestJet
Sun 6/28:00 amYWG - MDW
1 stop14h 01mWestJet
Deal found 5/2$460
Sun 6/166:56 amMDW - YWG
1 stop8h 26mMultiple Airlines
Sun 6/236:00 amYWG - MDW
1 stop10h 17mMultiple Airlines
Deal found 5/2$464

Midway to Winnipeg 2024 flight deals

Discover exclusive flight deals for travel between Midway and Winnipeg in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,864,334 searches. Data last updated May 3, 2024.
The lowest fares we've come across on flights traveling from Chicago to Winnipeg in May and June 2024. Check back soon for alternative fares.
Wed 6/196:00 amMDW - YWG
1 stop9h 22mWestJet
Wed 8/218:00 amYWG - MDW
1 stop13h 47mWestJet
Deal found 5/2$381
Tue 6/112:24 pmMDW - YWG
1 stop9h 05mDelta
Sat 6/156:55 amYWG - MDW
2 stops10h 09mDelta
Deal found 5/2$394
Tue 6/49:46 amMDW - YWG
2 stops12h 54mWestJet
Fri 6/78:50 pmYWG - MDW
2 stops13h 01mWestJet
Deal found 5/2$416
Thu 5/302:15 pmMDW - YWG
1 stop9h 08mWestJet
Thu 6/65:35 pmYWG - MDW
1 stop25h 01mWestJet
Deal found 5/2$418
Tue 6/119:34 amMDW - YWG
2 stops28h 05mWestJet
Sat 6/156:50 amYWG - MDW
2 stops10h 14mWestJet
Deal found 5/2$434
Tue 6/49:46 amMDW - YWG
2 stops12h 54mWestJet
Fri 6/712:26 pmYWG - MDW
1 stop6h 10mWestJet
Deal found 5/2$442
Thu 5/303:45 pmMDW - YWG
1 stop23h 40mWestJet
Sun 6/28:00 amYWG - MDW
1 stop14h 01mWestJet
Deal found 5/2$449
Thu 5/309:32 amMDW - YWG
2 stops11h 40mWestJet
Sun 6/28:00 amYWG - MDW
1 stop14h 01mWestJet
Deal found 5/2$460
Sun 6/166:56 amMDW - YWG
1 stop8h 26mMultiple Airlines
Sun 6/236:00 amYWG - MDW
1 stop10h 17mMultiple Airlines
Deal found 5/2$464

One-way flights to Winnipeg from Midway

Search for one-way flight options from Midway to Winnipeg. 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 2,864,334 searches. Data last updated May 3, 2024.
Users in need of a one-way flight from Chicago to Winnipeg can choose from these deals. Those needing a return flight from Chicago to Winnipeg can use the search form above.
Wed 5/297:53 amMDW - YWG
1 stop7h 32mMultiple Airlines
Deal found 5/2$131
Wed 5/299:46 amMDW - YWG
2 stops14h 11mWestJet
Deal found 5/2$181
Fri 6/711:26 amMDW - YWG
1 stop13h 18mMultiple Airlines
Deal found 5/2$182
Wed 6/199:34 amMDW - YWG
2 stops11h 38mWestJet
Deal found 5/2$193
Fri 6/710:39 amMDW - YWG
2 stops27h 00mWestJet
Deal found 5/2$198
Thu 6/206:00 amMDW - YWG
2 stops17h 57mWestJet
Deal found 5/2$216
Thu 6/202:24 pmMDW - YWG
1 stop9h 05mDelta
Deal found 5/2$514

Find flights from Midway to Winnipeg within your budget

Customize your flight search to find flights from Midway to Winnipeg 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 2,864,334 searches. Data last updated May 3, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$381 - $561

Route

Depart

Return

Price

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 6/19

1 stop9h 22m

Winnipeg

Wed 8/21

1 stop13h 47m

$381

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 6/11

1 stop9h 05m

Winnipeg

Sat 6/15

2 stops10h 09m

$394

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 6/4

2 stops12h 54m

Winnipeg

Fri 6/7

2 stops13h 01m

$416

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 5/30

1 stop9h 08m

Winnipeg

Thu 6/6

1 stop25h 01m

$418

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 6/11

2 stops28h 05m

Winnipeg

Sat 6/15

2 stops10h 14m

$434

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 6/16

1 stop8h 26m

Winnipeg

Sun 6/23

1 stop10h 17m

$464

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 6/11

1 stop9h 05m

Winnipeg

Thu 6/13

2 stops9h 34m

$491

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 6/11

2 stops13h 55m

Winnipeg

Thu 6/13

2 stops9h 34m

$501

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 6/16

1 stop8h 26m

Winnipeg

Sun 6/23

2 stops9h 47m

$561

Flights are sorted by cheapest first

Deals found on 5/2

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

Average price of flights to Winnipeg by month

Plan your trip from Midway to Winnipeg by taking into account the cheapest months to travel. The average price of a one-way flight from Midway to Winnipeg is currently $231 while a round-trip flight costs $451. Price data was last updated on April 28, 2024.

Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Winnipeg (average of $388). Flying from Chicago Midway Airport to Winnipeg in July is currently the most expensive (average of $574). 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

$495

February

$514

March

$426

April

$506

May

$521

June

$568

July

$574

August

$524

September

$492

October

$516

November

$388

December

$406

Temperature and rainfall in Winnipeg by month

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

YWG

Temperature

3.2 - 68 °F

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. 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 Winnipeg. Reviews last updated May 3, 2024.
To help decide which airline to fly from Chicago to Winnipeg, see what other customers have to say about WestJet and Delta. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.1
Very good
10,848 reviews
Check prices

Crew

8.6

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Food

7.4

Overall

8.1

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Delta
8.1
Very good
10,848 reviews
Delta
8.1
Very good
10,848 reviews
Check prices

Crew

8.6

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Food

7.4

Overall

8.1

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

WestJet
7.6
Good
2,965 reviews
Delta
8.1
Very good
10,848 reviews
Check prices

Crew

8.6

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Food

7.4

Overall

8.1

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Related info for your journey

Find useful and relevant information for your journey from Midway to Winnipeg. 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 into for flights to Winnipeg from Chicago Midway?

    Located just 4.6 mi from the city center, Winnipeg is the airport most travelers will use when flying to Winnipeg from Chicago Midway. Booking flights from Chicago Midway to Winnipeg (YWG) should be relatively easy as there are 0 daily inbound flights from Chicago Midway from 0 different airlines.

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

    Yes, there are multiple flights from Chicago Midway Airport to Winnipeg for under $400. The cheapest flight booked recently is on WestJet for just $381, but on average you can expect to pay $485.

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

    Cheapflights users have booked flights from Chicago Midway Airport to Winnipeg round-trip from $381. Another airline that can offer you cheap pricing is Delta.

  • What does MDW to YWG mean?

    MDW and YWG are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. MDW to YWG refers to a flight route from Chicago Midway Airport to Winnipeg Airport.

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

    The amount of baggage you can bring on your Midway to Winnipeg 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 Midway to Winnipeg with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to Winnipeg 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 Midway to Winnipeg that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Winnipeg 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 Midway to Winnipeg that allow pets onboard?

    Many airlines flying from Midway to Winnipeg 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 Midway to Winnipeg?

    Yes, you can often find last-minute deals on Midway to Winnipeg 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 Chicago Midway Airport to Winnipeg flight deals updated?

    The Chicago Midway Airport to Winnipeg flight deals you see on this page were last updated on 5/2.

See more FAQs

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Search flights from Midway to Winnipeg by cabin class

Find flights from Midway to Winnipeg, 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 Midway to Winnipeg?

Cheapflights makes it easy to find Midway to Winnipeg 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 Midway to Winnipeg?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Midway to Winnipeg for you. Better yet — we are completely free to use.

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

Yes! Cheapflights helps users easily find flights from Midway to Winnipeg with no change fees.

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

Yes, Cheapflights offers price alerts on Midway to Winnipeg flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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