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Cheap flights from Midway (MDW) to Winnipeg (YWG) from $371

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/14. 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
Jun 11 — Jun 181
From?
To?
Tue 6/11
Tue 6/18
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 June 6, 2024.

Round-trip from

$388
From Chicago Midway to Winnipeg
Search Deals

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 29 days in advance to save up to 490% 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 29 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 $1,097 for flights within the next 24 hours.

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

March is one of the best times of the year to fly to Winnipeg from Chicago Midway Airport. Prices for March average $593 per person but you can even find prices for as low as $205. The most expensive prices can be found in the month of July. Opting for a March flight can save you 54% on your journey compared to booking in July

What is the cheapest time of day to fly from MDW to 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 Midway to Winnipeg flights in June & July 2024

Find cheap flight options from Midway to Winnipeg specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Prices were last updated on June 6, 2024.
The lowest fares we've come across on flights traveling from Chicago to Winnipeg in June and July 2024. Check back soon for alternative fares.
Fri 6/1411:26 amMDW - YWG
1 stop13h 18mMultiple Airlines
Sun 6/3011:50 amYWG - MDW
2 stops9h 47mMultiple Airlines
Deal found 6/4$371
Mon 7/228:00 amMDW - YWG
2 stops9h 52mPorter Airlines
Fri 7/266:00 amYWG - MDW
2 stops15h 37mPorter Airlines
Deal found 6/5$499
Fri 6/1411:26 amMDW - YWG
1 stop13h 18mMultiple Airlines
Sun 6/308:00 amYWG - MDW
1 stop9h 05mMultiple Airlines
Deal found 6/4$518
Fri 6/149:08 pmMDW - YWG
3 stops20h 59mMultiple Airlines
Sun 6/3011:50 amYWG - MDW
2 stops9h 47mMultiple Airlines
Deal found 6/4$519
Fri 6/148:00 amMDW - YWG
2 stops10h 07mPorter Airlines
Sun 6/3011:50 amYWG - MDW
2 stops9h 47mPorter Airlines
Deal found 6/4$522
Mon 7/225:15 pmMDW - YWG
3 stops21h 12mMultiple Airlines
Fri 7/269:35 amYWG - MDW
2 stops12h 02mMultiple Airlines
Deal found 6/5$538
Mon 7/225:15 pmMDW - YWG
3 stops21h 12mMultiple Airlines
Fri 7/264:15 pmYWG - MDW
3 stops19h 17mMultiple Airlines
Deal found 6/5$640
Mon 7/222:49 pmMDW - YWG
1 stop8h 39mWestJet
Fri 7/266:55 amYWG - MDW
1 stop11h 44mWestJet
Deal found 6/5$712
Thu 7/187:19 pmMDW - YWG
1 stop4h 09mDelta
Mon 7/226:55 amYWG - MDW
2 stops10h 08mDelta
Deal found 6/5$716

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 3,050,429 searches. Data last updated June 6, 2024.
The lowest fares we've come across on flights traveling from Chicago to Winnipeg in June and July 2024. Check back soon for alternative fares.
Fri 6/1411:26 amMDW - YWG
1 stop13h 18mMultiple Airlines
Sun 6/3011:50 amYWG - MDW
2 stops9h 47mMultiple Airlines
Deal found 6/4$371
Mon 7/228:00 amMDW - YWG
2 stops9h 52mPorter Airlines
Fri 7/266:00 amYWG - MDW
2 stops15h 37mPorter Airlines
Deal found 6/5$499
Fri 6/1411:26 amMDW - YWG
1 stop13h 18mMultiple Airlines
Sun 6/308:00 amYWG - MDW
1 stop9h 05mMultiple Airlines
Deal found 6/4$518
Fri 6/149:08 pmMDW - YWG
3 stops20h 59mMultiple Airlines
Sun 6/3011:50 amYWG - MDW
2 stops9h 47mMultiple Airlines
Deal found 6/4$519
Fri 6/148:00 amMDW - YWG
2 stops10h 07mPorter Airlines
Sun 6/3011:50 amYWG - MDW
2 stops9h 47mPorter Airlines
Deal found 6/4$522
Mon 7/225:15 pmMDW - YWG
3 stops21h 12mMultiple Airlines
Fri 7/269:35 amYWG - MDW
2 stops12h 02mMultiple Airlines
Deal found 6/5$538
Mon 7/225:15 pmMDW - YWG
3 stops21h 12mMultiple Airlines
Fri 7/264:15 pmYWG - MDW
3 stops19h 17mMultiple Airlines
Deal found 6/5$640
Sat 8/37:19 pmMDW - YWG
1 stop4h 12mWestJet
Sat 8/106:30 amYWG - MDW
2 stops12h 06mWestJet
Deal found 6/4$708
Mon 7/222:49 pmMDW - YWG
1 stop8h 39mWestJet
Fri 7/266:55 amYWG - MDW
1 stop11h 44mWestJet
Deal found 6/5$712

Midway to Winnipeg flights leaving soon

Find last-minute flight options from Midway to Winnipeg 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 3,050,429 searches. Data last updated June 6, 2024.
Check out these flights departing soon from Chicago to Winnipeg. Users should examine the flight details to ensure there are no surprises.
Fri 6/1411:26 amMDW - YWG
1 stop13h 18mMultiple Airlines
Sun 6/3011:50 amYWG - MDW
2 stops9h 47mMultiple Airlines
Deal found 6/4$371
Fri 6/1411:26 amMDW - YWG
1 stop13h 18mMultiple Airlines
Sun 6/308:00 amYWG - MDW
1 stop9h 05mMultiple Airlines
Deal found 6/4$518
Fri 6/149:08 pmMDW - YWG
3 stops20h 59mMultiple Airlines
Sun 6/3011:50 amYWG - MDW
2 stops9h 47mMultiple Airlines
Deal found 6/4$519
Fri 6/148:00 amMDW - YWG
2 stops10h 07mPorter Airlines
Sun 6/3011:50 amYWG - MDW
2 stops9h 47mPorter Airlines
Deal found 6/4$522
Tue 6/119:29 amMDW - YWG
1 stop7h 08mWestJet
Thu 6/1312:26 pmYWG - MDW
1 stop6h 10mWestJet
Deal found 6/5$958
Tue 6/111:24 pmMDW - YWG
2 stops10h 05mDelta
Thu 6/1312:26 pmYWG - MDW
1 stop6h 10mDelta
Deal found 6/5$1,019
Tue 6/111:24 pmMDW - YWG
2 stops10h 05mDelta
Thu 6/136:55 amYWG - MDW
2 stops10h 09mDelta
Deal found 6/5$1,154

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 3,050,429 searches. Data last updated June 6, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$499 - $793

Route

Depart

Return

Price

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 7/22

2 stops9h 52m

Winnipeg

Fri 7/26

2 stops15h 37m

$499

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 7/22

3 stops21h 12m

Winnipeg

Fri 7/26

2 stops12h 02m

$538

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 7/22

3 stops21h 12m

Winnipeg

Fri 7/26

3 stops19h 17m

$640

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 8/3

1 stop4h 12m

Winnipeg

Sat 8/10

2 stops12h 06m

$708

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 7/22

1 stop8h 39m

Winnipeg

Fri 7/26

1 stop11h 44m

$712

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 7/18

1 stop4h 09m

Winnipeg

Mon 7/22

2 stops10h 08m

$716

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 7/22

1 stop8h 39m

Winnipeg

Fri 7/26

2 stops11h 09m

$723

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 6/21

1 stop14h 00m

Winnipeg

Tue 6/25

1 stop11h 41m

$749

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 7/18

1 stop4h 09m

Winnipeg

Mon 7/22

1 stop7h 14m

$793

Flights are sorted by cheapest first

Deals found on 6/5

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

Best time to book a flight from Midway to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

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

If weather is an important factor for your trip to Winnipeg, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 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 June 6, 2024.
To help decide which airline to fly from Chicago to Winnipeg, see what other customers have to say about WestJet, Delta and Porter Airlines. 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
8.0
Very good
10,368 reviews

Entertainment

8.0

Crew

8.6

Overall

8.0

Food

7.4

Boarding

8.2

Comfort

7.9

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
8.0
Very good
10,368 reviews
Delta
8.0
Very good
10,368 reviews

Entertainment

8.0

Crew

8.6

Overall

8.0

Food

7.4

Boarding

8.2

Comfort

7.9

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
7.5
Good
2,856 reviews
Delta
8.0
Very good
10,368 reviews

Entertainment

8.0

Crew

8.6

Overall

8.0

Food

7.4

Boarding

8.2

Comfort

7.9

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.

Porter Airlines
7.4
Good
382 reviews
Delta
8.0
Very good
10,368 reviews

Entertainment

8.0

Crew

8.6

Overall

8.0

Food

7.4

Boarding

8.2

Comfort

7.9

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 $500 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Winnipeg for under $500. The cheapest flight booked recently is on Porter Airlines for just $499, but on average you can expect to pay $737.

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

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

  • 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 $499. Other airlines that can offer you cheap pricing are WestJet, from $708, and Delta, from $716.

  • 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 6/5.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Winnipeg?

    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 August is currently the most expensive (average of $573). 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.

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Search flights from Midway to Winnipeg by cabin class

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