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Cheap flights from Winnipeg to Indiana from C$ 182

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 26/11. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — IND
29 Nov — 6 Dec1
1 adult
1 adult, Economy, 0 bags

Find flight deals from Winnipeg to Indiana

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to Indiana
Explore the most affordable flight options available from Winnipeg to Indiana. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 30 October 2025.

Fri 5/127:30 a.m.YWG - ORD
1 stop28h 24mMultiple Airlines
Sun 7/1210:24 a.m.ORD - YWG
2 stops14h 17mMultiple Airlines
Deal found 29/10C$ 276
Wed 26/117:30 a.m.YWG - ORD
1 stop16h 38mMultiple Airlines
Wed 3/128:00 a.m.ORD - YWG
2 stops16h 41mMultiple Airlines
Deal found 29/10C$ 297
Thu 4/129:00 p.m.YWG - MDW
2 stops25h 12mMultiple Airlines
Sun 7/126:15 a.m.MDW - YWG
1 stop8h 52mMultiple Airlines
Deal found 29/10C$ 299
Tue 11/119:00 p.m.YWG - MDW
2 stops15h 41mMultiple Airlines
Tue 18/111:56 p.m.MDW - YWG
1 stop25h 11mMultiple Airlines
Deal found 29/10C$ 300
Tue 11/119:00 p.m.YWG - ORD
2 stops14h 14mMultiple Airlines
Tue 18/1112:37 p.m.ORD - YWG
1 stop26h 30mMultiple Airlines
Deal found 29/10C$ 300
Thu 4/129:00 p.m.YWG - ORD
2 stops17h 40mMultiple Airlines
Sun 7/126:11 a.m.ORD - YWG
1 stop8h 56mMultiple Airlines
Deal found 29/10C$ 341
Fri 5/127:30 a.m.YWG - ORD
1 stop28h 24mMultiple Airlines
Mon 8/129:27 p.m.ORD - YWG
2 stops27h 12mMultiple Airlines
Deal found 28/10C$ 350
Sat 15/119:00 p.m.YWG - ORD
2 stops27h 11mMultiple Airlines
Sat 13/121:24 p.m.ORD - YWG
1 stop25h 43mMultiple Airlines
Deal found 28/10C$ 371
Fri 28/117:30 a.m.YWG - MDW
1 stop7h 10mMultiple Airlines
Fri 5/128:42 p.m.MDW - YWG
2 stops27h 59mMultiple Airlines
Deal found 29/10C$ 383
Fri 21/117:30 a.m.YWG - MDW
1 stop7h 10mMultiple Airlines
Tue 25/116:05 a.m.MDW - YWG
2 stops18h 36mMultiple Airlines
Deal found 29/10C$ 398
Fri 21/117:30 a.m.YWG - MDW
1 stop7h 10mMultiple Airlines
Sun 23/116:05 a.m.MDW - YWG
1 stop9h 02mMultiple Airlines
Deal found 30/10C$ 465
Wed 26/118:40 a.m.YWG - SDF
2 stops24h 19mUnited Airlines
Wed 3/127:00 a.m.SDF - YWG
1 stop5h 57mUnited Airlines
Deal found 29/10C$ 487

Cheap flight deals from Winnipeg to Indiana

Keep the following information in mind while searching for Winnipeg to Indiana flight deals. Data was last updated 30 October 2025.

Round-trip from

C$ 276

One-way from

C$ 182

Popular in

January

Cheapest in

March

Average price

C$ 867
5/12-7/12
  • 5/12-7/12
  • 3 total stops
  • 42h 41m total
  • Winnipeg to Indiana
Search Deals
26/11
  • 26/11
  • 1 total stop
  • 15h 13m total
  • Winnipeg to Indiana
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (C$ 175 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 44 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Indiana 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 629,999 searches. Data last updated 30 October 2025.
Use the filters below to find and compare flights from Winnipeg to Indiana that are best for you.

Fly from

Winnipeg

Fly to

Indiana

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/12

7:30 a.m.-11:54 a.m.

1 stop28h 24m

Chicago O'Hare Intl

Sun 7/12

6:11 a.m.-3:07 p.m.

1 stop8h 56m

C$ 282

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 26/11

7:30 a.m.-12:08 a.m.

1 stop16h 38m

Chicago O'Hare Intl

Wed 3/12

8:00 a.m.-12:41 a.m.

2 stops16h 41m

C$ 297

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 4/12

9:00 p.m.-10:12 p.m.

2 stops25h 12m

Chicago Midway

Sun 7/12

6:15 a.m.-3:07 p.m.

1 stop8h 52m

C$ 299

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 11/11

9:00 p.m.-12:41 p.m.

2 stops15h 41m

Chicago Midway

Tue 18/11

1:56 p.m.-3:07 p.m.

1 stop25h 11m

C$ 332

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/12

7:30 a.m.-11:54 a.m.

1 stop28h 24m

Chicago O'Hare Intl

Mon 8/12

7:10 a.m.-6:03 p.m.

1 stop10h 53m

C$ 369

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 28/11

7:30 a.m.-2:40 p.m.

1 stop7h 10m

Chicago Midway

Fri 5/12

8:42 p.m.-12:41 a.m.

2 stops27h 59m

C$ 383

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 21/11

7:30 a.m.-2:40 p.m.

1 stop7h 10m

Chicago Midway

Tue 25/11

6:05 a.m.-12:41 a.m.

2 stops18h 36m

C$ 398

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 21/11

7:30 a.m.-12:08 a.m.

1 stop16h 38m

Chicago O'Hare Intl

Tue 25/11

11:48 a.m.-3:07 p.m.

2 stops27h 19m

C$ 447

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 11/11

9:00 p.m.-8:27 p.m.

3 stops23h 27m

Chicago O'Hare Intl

Thu 13/11

10:52 a.m.-8:06 p.m.

3 stops33h 14m

C$ 473

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Tue 10/3

2:15 p.m.-8:14 p.m.

1 stop4h 59m

Louisville Intl

Wed 11/3

9:35 a.m.-11:39 a.m.

2 stops27h 04m

C$ 487

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/10

Showing 1-10 of 49 results
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Best time to book a flight from Winnipeg to Indiana

Have a flexible travel schedule? Discover the best time to fly to Indiana from Winnipeg 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.

Cheapflights Insights

Everything you need to know about your flight from Winnipeg to Indiana

What is the cheapest month to book a flight from Winnipeg to Indiana?

Currently, April is the cheapest month in which you can book a flight from Winnipeg to Indiana (average of C$ 644). Flying from Winnipeg to Indiana in September is currently the most expensive (average of C$ 1,197). 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.

What is the cheapest time of day to fly from YWG to IN?

Find hourly flight availability from Winnipeg to Indiana. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 30 October 2025.

It’s optimal to fly from Winnipeg to Indiana at noon. By choosing this option you can save up to 25% on the cost of your flight, compared to a flight in the afternoon.

Reviews of airlines servicing Indiana

Get insights into the airlines that provide service to Indiana. 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 Indiana. Reviews last updated 30 October 2025.
Check out reviews from past customers who have flown with WestJet and Air Canada from Winnipeg to Indiana to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,152 reviews
Check prices

Comfort

7.1

Entertainment

6.1

Crew

7.9

Overall

7.2

Boarding

7.4

Food

6.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.
WestJet
7.2
Good
3,152 reviews
WestJet
7.2
Good
3,152 reviews
Check prices

Comfort

7.1

Entertainment

6.1

Crew

7.9

Overall

7.2

Boarding

7.4

Food

6.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.
Air Canada
7.1
Good
10,381 reviews
WestJet
7.2
Good
3,152 reviews
Check prices

Comfort

7.1

Entertainment

6.1

Crew

7.9

Overall

7.2

Boarding

7.4

Food

6.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Indiana. 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 Indiana?

    For a flight from Winnipeg to Indiana, you will be flying from Winnipeg. Winnipeg (YWG) is just 7.3 km from the centre of the city.

  • How long is the flight from Winnipeg to Indiana?

    For as low as C$ 487, United Airlines can have you in Indiana from Winnipeg in 4h 59m. Winnipeg and Indiana are separated by a distance of 1590 km.

  • What are the most popular routes from Winnipeg to Indiana?

    The most popular flight routes from Winnipeg to Indiana are Winnipeg - Chicago O'Hare Intl, Winnipeg - Chicago Midway and Winnipeg - Indianapolis.

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

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

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

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

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

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

  • What is the cheapest month to book a flight from Winnipeg to Indiana?

    Currently, April is the cheapest month in which you can book a flight from Winnipeg to Indiana (average of C$ 644). Flying from Winnipeg to Indiana in September is currently the most expensive (average of C$ 1,197). 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.

See more FAQs

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Top 2 airlines flying from Winnipeg to Indiana

Discover the top 2 airlines that operate flights from Winnipeg to Indiana. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 30 October 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 665AverageC$ 811FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 666AverageC$ 1,005FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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 Indiana?

When you search for this flight from Winnipeg to Indiana, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

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

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 Indiana.

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

Need flexible booking options for your flight to Indiana from Winnipeg? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

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

Not ready to book yet? You can track prices for flights from Winnipeg to Indiana on Cheapflights with our Price Alert feature and get notified when better prices are available.

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