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Cheap flights from Midway (MDW) to Winnipeg (YWG) from $386

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 6/18. 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 15 — May 221
From?
To?
Wed 5/15
Wed 5/22
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 10, 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 $600 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 63% on your journey compared to booking in July

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 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 2,717,708 searches. Data last updated May 10, 2024.
Take a peek at the cheapest Delta flights we've detected traveling from Chicago to Winnipeg. Make sure to double check the flight details before booking.
Tue 6/112:24 pmMDW - YWG
1 stop9h 05mDelta
Thu 6/136:55 amYWG - MDW
2 stops10h 09mDelta
Deal found 5/8$411
Tue 6/111:24 pmMDW - YWG
2 stops10h 05mDelta
Thu 6/136:55 amYWG - MDW
2 stops10h 09mDelta
Deal found 5/8$416
Mon 6/172:24 pmMDW - YWG
1 stop9h 05mDelta
Fri 6/216:55 amYWG - MDW
2 stops10h 09mDelta
Deal found 5/8$480
Thu 7/181:24 pmMDW - YWG
2 stops10h 01mDelta
Mon 7/228:00 amYWG - MDW
1 stop6h 54mDelta
Deal found 5/8$566
Mon 9/309:20 amMDW - YWG
1 stop7h 27mDelta
Thu 10/38:00 amYWG - MDW
1 stop6h 56mDelta
Deal found 5/9$567
Thu 7/181:24 pmMDW - YWG
2 stops10h 01mDelta
Mon 7/227:30 amYWG - MDW
2 stops9h 35mDelta
Deal found 5/8$576
Thu 7/187:06 pmMDW - YWG
1 stop4h 19mDelta
Mon 7/228:00 amYWG - MDW
1 stop6h 54mDelta
Deal found 5/9$577
Thu 7/181:24 pmMDW - YWG
2 stops10h 01mDelta
Mon 7/228:00 amYWG - MDW
1 stop6h 54mDelta
Deal found 5/9$587
Thu 7/181:24 pmMDW - YWG
2 stops10h 01mDelta
Mon 7/227:30 amYWG - MDW
2 stops9h 35mDelta
Deal found 5/9$598

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 2,717,708 searches. Data last updated May 10, 2024.
Browse through some of the cheapest WestJet flights traveling from Chicago to Winnipeg. Deals are refreshing constantly so come back soon for more options.
Tue 6/49:46 amMDW - YWG
1 stop13h 37mWestJet
Wed 6/128:00 amYWG - MDW
1 stop13h 46mWestJet
Deal found 5/8$410
Tue 6/49:46 amMDW - YWG
2 stops12h 54mWestJet
Wed 6/128:00 amYWG - MDW
1 stop9h 59mWestJet
Deal found 5/8$415
Tue 6/49:46 amMDW - YWG
2 stops12h 54mWestJet
Wed 6/126:50 amYWG - MDW
2 stops10h 14mWestJet
Deal found 5/8$432
Tue 6/119:29 amMDW - YWG
1 stop14h 00mWestJet
Wed 6/128:00 amYWG - MDW
1 stop13h 46mWestJet
Deal found 5/8$451
Tue 6/119:29 amMDW - YWG
1 stop14h 00mWestJet
Wed 6/127:30 amYWG - MDW
2 stops14h 16mWestJet
Deal found 5/8$461
Tue 6/119:29 amMDW - YWG
2 stops14h 28mWestJet
Wed 6/127:30 amYWG - MDW
2 stops14h 16mWestJet
Deal found 5/8$472
Tue 6/119:34 amMDW - YWG
2 stops11h 38mWestJet
Wed 6/128:00 amYWG - MDW
1 stop13h 46mWestJet
Deal found 5/7$491
Tue 6/119:34 amMDW - YWG
2 stops11h 38mWestJet
Wed 6/127:30 amYWG - MDW
2 stops9h 34mWestJet
Deal found 5/7$502
Mon 9/301:10 pmMDW - YWG
2 stops11h 23mWestJet
Thu 10/38:00 amYWG - MDW
1 stop6h 56mWestJet
Deal found 5/9$516

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 2,717,708 searches. Prices were last updated on May 10, 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.
Tue 6/182:24 pmMDW - YWG
1 stop9h 05mDelta
Mon 6/2412:26 pmYWG - MDW
1 stop6h 10mDelta
Deal found 5/9$386
Tue 6/182:24 pmMDW - YWG
1 stop9h 05mDelta
Mon 6/246:55 amYWG - MDW
2 stops5h 48mDelta
Deal found 5/9$396
Tue 6/1812:45 pmMDW - YWG
2 stops10h 44mDelta
Mon 6/246:55 amYWG - MDW
2 stops5h 48mDelta
Deal found 5/9$401
Tue 6/119:29 amMDW - YWG
1 stop14h 00mWestJet
Wed 6/128:00 amYWG - MDW
1 stop13h 46mWestJet
Deal found 5/8$451
Tue 6/119:29 amMDW - YWG
1 stop14h 00mWestJet
Wed 6/127:30 amYWG - MDW
2 stops14h 16mWestJet
Deal found 5/8$461
Tue 6/119:29 amMDW - YWG
2 stops14h 28mWestJet
Wed 6/127:30 amYWG - MDW
2 stops14h 16mWestJet
Deal found 5/8$472
Mon 6/172:24 pmMDW - YWG
1 stop9h 05mDelta
Fri 6/216:55 amYWG - MDW
2 stops10h 09mDelta
Deal found 5/8$480
Tue 6/116:00 amMDW - YWG
2 stops15h 12mWestJet
Wed 6/127:30 amYWG - MDW
2 stops9h 34mWestJet
Deal found 5/9$487
Sun 5/129:46 amMDW - YWG
1 stop6h 59mWestJet
Sat 5/257:30 amYWG - MDW
2 stops8h 43mWestJet
Deal found 5/9$518

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 2,717,708 searches. Data last updated May 10, 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.
Tue 6/182:24 pmMDW - YWG
1 stop9h 05mDelta
Mon 6/2412:26 pmYWG - MDW
1 stop6h 10mDelta
Deal found 5/9$386
Tue 6/182:24 pmMDW - YWG
1 stop9h 05mDelta
Mon 6/246:55 amYWG - MDW
2 stops5h 48mDelta
Deal found 5/9$396
Tue 6/1812:45 pmMDW - YWG
2 stops10h 44mDelta
Mon 6/246:55 amYWG - MDW
2 stops5h 48mDelta
Deal found 5/9$401
Tue 6/119:29 amMDW - YWG
1 stop14h 00mWestJet
Wed 6/128:00 amYWG - MDW
1 stop13h 46mWestJet
Deal found 5/8$451
Tue 6/119:29 amMDW - YWG
1 stop14h 00mWestJet
Wed 6/127:30 amYWG - MDW
2 stops14h 16mWestJet
Deal found 5/8$461
Tue 6/119:29 amMDW - YWG
2 stops14h 28mWestJet
Wed 6/127:30 amYWG - MDW
2 stops14h 16mWestJet
Deal found 5/8$472
Mon 6/172:24 pmMDW - YWG
1 stop9h 05mDelta
Fri 6/216:55 amYWG - MDW
2 stops10h 09mDelta
Deal found 5/8$480
Tue 6/116:00 amMDW - YWG
2 stops15h 12mWestJet
Wed 6/127:30 amYWG - MDW
2 stops9h 34mWestJet
Deal found 5/9$487
Wed 8/289:35 amMDW - YWG
2 stops14h 52mWestJet
Fri 8/305:38 pmYWG - MDW
1 stop24h 28mWestJet
Deal found 5/9$507

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 2,717,708 searches. Data last updated May 10, 2024.
Check out these flights departing soon from Chicago to Winnipeg. Users should examine the flight details to ensure there are no surprises.
Sun 5/129:46 amMDW - YWG
1 stop6h 59mWestJet
Sat 5/257:30 amYWG - MDW
2 stops8h 43mWestJet
Deal found 5/9$518
Thu 5/166:00 amMDW - YWG
2 stops15h 12mWestJet
Sun 5/266:55 amYWG - MDW
1 stop4h 07mWestJet
Deal found 5/8$584
Thu 5/169:46 amMDW - YWG
1 stop13h 37mWestJet
Sun 5/266:55 amYWG - MDW
1 stop4h 07mWestJet
Deal found 5/8$608
Sun 5/1212:42 pmMDW - YWG
2 stops11h 51mWestJet
Sat 5/257:30 amYWG - MDW
2 stops8h 43mWestJet
Deal found 5/9$814
Tue 5/148:45 amMDW - YWG
2 stops12h 27mWestJet
Fri 5/177:50 pmYWG - MDW
2 stops14h 21mWestJet
Deal found 5/9$849
Tue 5/148:45 amMDW - YWG
2 stops12h 27mWestJet
Fri 5/1712:22 pmYWG - MDW
1 stop5h 45mWestJet
Deal found 5/9$859
Thu 5/169:32 amMDW - YWG
2 stops11h 40mDelta
Sun 5/266:55 amYWG - MDW
2 stops9h 18mDelta
Deal found 5/8$881
Tue 5/149:46 amMDW - YWG
1 stop6h 59mWestJet
Fri 5/1712:22 pmYWG - MDW
1 stop5h 45mWestJet
Deal found 5/9$983
Sun 5/129:46 amMDW - YWG
1 stop6h 59mWestJet
Sat 5/256:55 amYWG - MDW
1 stop4h 07mWestJet
Deal found 5/9$1,030

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 2,717,708 searches. Data last updated May 10, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$410 - $554

Route

Depart

Return

Price

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 6/4

1 stop13h 37m

Winnipeg

Wed 6/12

1 stop13h 46m

$410

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 6/11

1 stop9h 05m

Winnipeg

Thu 6/13

2 stops10h 09m

$411

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 6/4

2 stops12h 54m

Winnipeg

Wed 6/12

1 stop9h 59m

$415

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 6/11

2 stops10h 05m

Winnipeg

Thu 6/13

2 stops10h 09m

$416

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 6/4

2 stops12h 54m

Winnipeg

Wed 6/12

2 stops10h 14m

$432

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 6/11

1 stop14h 00m

Winnipeg

Wed 6/12

1 stop13h 46m

$451

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 6/11

1 stop14h 00m

Winnipeg

Wed 6/12

2 stops14h 16m

$461

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 6/17

1 stop9h 05m

Winnipeg

Fri 6/21

2 stops10h 09m

$480

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 6/17

1 stop7h 52m

Winnipeg

Fri 6/21

1 stop13h 46m

$554

Flights are sorted by cheapest first

Deals found on 5/8

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 $0 while a round-trip flight costs $448. Price data was last updated on May 5, 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 $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.

January

$495

February

$514

March

$426

April

$506

May

$521

June

$549

July

$573

August

$534

September

$492

October

$495

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 10, 2024.
To help decide which airline to fly from Chicago to Winnipeg, see what other customers have to say about Delta and WestJet. 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
10,768 reviews
Check prices

Overall

8.0

Comfort

7.9

Food

7.4

Entertainment

8.0

Boarding

8.2

Crew

8.6

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
10,768 reviews
Delta
8.0
Very good
10,768 reviews
Check prices

Overall

8.0

Comfort

7.9

Food

7.4

Entertainment

8.0

Boarding

8.2

Crew

8.6

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
2,940 reviews
Delta
8.0
Very good
10,768 reviews
Check prices

Overall

8.0

Comfort

7.9

Food

7.4

Entertainment

8.0

Boarding

8.2

Crew

8.6

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 WestJet for just $410, but on average you can expect to pay $492.

  • Are there last-minute flights available from Chicago Midway Airport to Winnipeg for under $600?

    There are currently 12+ open flights from Chicago Midway Airport to Winnipeg within the next 7 days for less than $600.

  • 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 $410. 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 5/9.

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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