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Cheap flights from Winnipeg to Indiana from C$ 169

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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — IND
17 Jan — 24 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap 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 18 December 2025.

Wed 31/124:55 p.m.YWG - ORD
1 stop27h 28mMultiple Airlines
Sat 4/411:39 a.m.ORD - YWG
2 stops36h 08mMultiple Airlines
Deal found 17/12C$ 726
Wed 31/128:05 p.m.YWG - ORD
2 stops16h 07mWestJet
Sat 4/412:15 p.m.ORD - YWG
2 stops31h 09mWestJet
Deal found 17/12C$ 846
Mon 29/1212:20 p.m.YWG - MDW
2 stops20h 29mWestJet
Mon 5/19:50 a.m.MDW - YWG
1 stop25h 13mWestJet
Deal found 16/12C$ 853
Wed 24/124:55 p.m.YWG - ORD
1 stop27h 28mMultiple Airlines
Wed 31/126:35 a.m.ORD - YWG
2 stops29h 34mMultiple Airlines
Deal found 17/12C$ 865
Wed 31/125:00 a.m.YWG - MDW
2 stops12h 26mWestJet
Sat 4/410:49 a.m.MDW - YWG
1 stop28h 20mWestJet
Deal found 17/12C$ 872
Mon 29/1212:20 p.m.YWG - ORD
2 stops20h 41mWestJet
Mon 5/17:10 a.m.ORD - YWG
2 stops12h 02mWestJet
Deal found 16/12C$ 876
Wed 24/128:05 p.m.YWG - ORD
2 stops21h 49mWestJet
Wed 31/126:35 a.m.ORD - YWG
2 stops29h 34mWestJet
Deal found 17/12C$ 971
Wed 24/1212:35 p.m.YWG - MDW
1 stop22h 31mWestJet
Wed 31/125:59 p.m.MDW - YWG
2 stops29h 51mWestJet
Deal found 17/12C$ 1,051
Mon 22/126:40 a.m.YWG - IND
1 stop4h 29mWestJet
Fri 26/124:45 p.m.IND - YWG
1 stop7h 59mWestJet
Deal found 17/12C$ 1,055
Wed 24/122:20 p.m.YWG - ORD
Nonstop2h 43mUnited Airlines
Wed 31/123:55 p.m.ORD - YWG
1 stop7h 59mUnited Airlines
Deal found 17/12C$ 1,105
Wed 24/122:20 p.m.YWG - ORD
Nonstop2h 43mAir Canada
Wed 31/129:10 a.m.ORD - YWG
Nonstop2h 47mAir Canada
Deal found 17/12C$ 1,112
Mon 22/126:40 a.m.YWG - IND
1 stop8h 25mDelta
Fri 26/121:45 p.m.IND - YWG
2 stops10h 59mDelta
Deal found 16/12C$ 1,177

Find flight deals from Winnipeg to Indiana

Keep the following information in mind while searching for Winnipeg to Indiana flight deals. Data was last updated 18 December 2025.

Round-trip from

C$ 284

One-way from

C$ 169

Popular in

December

Cheapest in

March

Average price

C$ 1,345
13/1-20/1
  • 13/1-20/1
  • 3 total stops
  • 44h 06m total
  • Winnipeg to Indiana
Search Deals
12/1
  • 12/1
  • 2 total stops
  • 19h 52m total
  • Winnipeg to Indiana
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (C$ 226 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 51 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 18 December 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 - MDW

YWGMDW

Winnipeg

Wed 14/1

12:55 p.m.-11:47 a.m.

2 stops22h 52m

Chicago Midway

Mon 19/1

12:57 p.m.-12:43 a.m.

1 stop11h 46m

C$ 289

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 14/1

7:30 a.m.-4:52 p.m.

1 stop9h 22m

Chicago O'Hare Intl

Mon 19/1

11:48 a.m.-12:43 a.m.

1 stop12h 55m

C$ 300

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 16/1

5:05 p.m.-4:52 p.m.

1 stop23h 47m

Chicago O'Hare Intl

Sun 18/1

8:41 p.m.-12:43 a.m.

1 stop28h 02m

C$ 320

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 13/5

3:15 p.m.-4:43 p.m.

1 stop25h 28m

Chicago O'Hare Intl

Mon 18/5

5:30 p.m.-10:00 a.m.

1 stop16h 30m

C$ 322

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 7/6

8:30 a.m.-4:43 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Thu 11/6

5:30 p.m.-1:00 p.m.

2 stops19h 30m

C$ 331

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

5:00 p.m.-4:43 p.m.

2 stops23h 43m

Chicago O'Hare Intl

Thu 30/4

5:30 p.m.-11:00 p.m.

1 stop29h 30m

C$ 331

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 31/1

9:00 p.m.-11:45 a.m.

2 stops14h 45m

Chicago Midway

Sat 7/2

9:38 a.m.-3:09 p.m.

1 stop29h 31m

C$ 336

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 13/1

8:00 a.m.-5:52 p.m.

1 stop9h 52m

Chicago O'Hare Intl

Tue 20/1

2:53 p.m.-3:07 p.m.

1 stop24h 14m

C$ 339

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 13/1

9:00 p.m.-10:31 a.m.

2 stops13h 31m

Chicago Midway

Tue 20/1

1:20 p.m.-3:07 p.m.

1 stop25h 47m

C$ 344

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 16/5

6:30 p.m.-4:43 p.m.

1 stop22h 13m

Chicago O'Hare Intl

Wed 20/5

5:30 p.m.-8:48 p.m.

2 stops27h 18m

C$ 364

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/12

Showing 1-10 of 45 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$ 635). Flying from Winnipeg to Indiana in December is currently the most expensive (average of C$ 1,244). 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 18 December 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 18 December 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
3,204 reviews
Check prices

Food

6.2

Boarding

7.4

Entertainment

6.1

Crew

7.9

Overall

7.2

Comfort

7.1

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
3,204 reviews
WestJet
7.2
Good
3,204 reviews
Check prices

Food

6.2

Boarding

7.4

Entertainment

6.1

Crew

7.9

Overall

7.2

Comfort

7.1

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
10,534 reviews
WestJet
7.2
Good
3,204 reviews
Check prices

Food

6.2

Boarding

7.4

Entertainment

6.1

Crew

7.9

Overall

7.2

Comfort

7.1

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$ 497, WestJet can have you in Indiana from Winnipeg in 4h 45m. Winnipeg and Indiana are separated by a distance of 1419 km. This flight may include one or multiple stops.

  • 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 - Louisville Intl.

  • 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$ 635). Flying from Winnipeg to Indiana in December is currently the most expensive (average of C$ 1,244). 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 18 December 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 695AverageC$ 795FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 750AverageC$ 991FlexibilityNo 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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