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Cheap flights from Indiana to Winnipeg from C$ 163

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 14/4. Fares are subject to change and may not be available on all flights or dates of travel.
IND — YWG
18 Mar — 25 Mar1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Indiana to Winnipeg

Enter your travel dates to find the best prices.

Cheapest flights from Indiana to Winnipeg
Explore the most affordable flight options available from Indiana to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 16 February 2026.

Fri 24/42:20 p.m.
ORD
-
YWG
1 stop8h 20m
WestJet
Sun 26/47:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 13/2C$ 310
Thu 14/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 17/57:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 12/2C$ 338
Fri 24/42:20 p.m.
ORD
-
YWG
1 stop8h 20m
Multiple Airlines
Sun 26/49:05 p.m.
YWG
-
ORD
2 stops17h 15m
Multiple Airlines
Deal found 13/2C$ 353
Tue 21/41:40 p.m.
ORD
-
YWG
1 stop25h 29m
Multiple Airlines
Tue 28/49:05 p.m.
YWG
-
ORD
2 stops21h 49m
Multiple Airlines
Deal found 14/2C$ 358
Thu 14/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Mon 18/54:55 p.m.
YWG
-
ORD
1 stop23h 45m
WestJet
Deal found 12/2C$ 368
Thu 14/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Mon 18/59:05 p.m.
YWG
-
ORD
2 stops21h 49m
Multiple Airlines
Deal found 12/2C$ 369
Thu 16/43:15 p.m.
ORD
-
YWG
1 stop23h 54m
Multiple Airlines
Thu 23/44:10 p.m.
YWG
-
ORD
2 stops24h 43m
Multiple Airlines
Deal found 12/2C$ 370
Thu 14/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Sun 17/59:05 p.m.
YWG
-
ORD
2 stops13h 39m
Multiple Airlines
Deal found 12/2C$ 380
Wed 4/36:02 p.m.
ORD
-
YWG
2 stops30h 38m
Multiple Airlines
Wed 11/37:30 a.m.
YWG
-
ORD
1 stop10h 27m
Multiple Airlines
Deal found 13/2C$ 399
Fri 5/65:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 7/67:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 15/2C$ 403
Tue 3/37:30 a.m.
MDW
-
YWG
2 stops17h 10m
Multiple Airlines
Wed 4/37:30 a.m.
YWG
-
MDW
1 stop11h 37m
Multiple Airlines
Deal found 14/2C$ 425
Mon 9/32:16 p.m.
MDW
-
YWG
1 stop10h 20m
Multiple Airlines
Fri 13/37:30 a.m.
YWG
-
MDW
1 stop14h 49m
Multiple Airlines
Deal found 12/2C$ 493

Find flight deals from Indiana to Winnipeg

Keep the following information in mind while searching for Indiana to Winnipeg flight deals. Data was last updated 16 February 2026.

Round-trip from

C$ 310

One-way from

C$ 163
WestJet
  • WestJet
  • 24/4-26/4
  • 2 total stops
  • 18h 00m total
  • Indiana to Winnipeg
Search Deals
14/4
  • 14/4
  • 2 total stops
  • 17h 22m total
  • Indiana to Winnipeg
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Indiana 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 629,999 searches. Data last updated 16 February 2026.
Use the filters below to find and compare flights from Indiana to Winnipeg that are best for you.

Fly from

Indiana

Fly to

Winnipeg

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Mon 8/6

9:05 p.m.-4:40 p.m.

1 stop19h 35m

C$ 368

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 14/5

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Mon 18/5

4:55 p.m.-4:40 p.m.

1 stop23h 45m

C$ 368

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Mon 8/6

9:05 p.m.-12:29 p.m.

2 stops15h 24m

C$ 408

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Sun 7/6

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 413

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 4/3

7:00 a.m.-11:32 a.m.

2 stops28h 32m

Winnipeg

Wed 11/3

7:30 a.m.-5:57 p.m.

1 stop10h 27m

C$ 430

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 24/4

2:20 p.m.-11:47 p.m.

2 stops9h 27m

Winnipeg

Sun 26/4

10:30 p.m.-4:40 p.m.

2 stops18h 10m

C$ 432

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 11/5

5:30 p.m.-11:10 a.m.

1 stop17h 40m

Winnipeg

Mon 1/6

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 460

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 9/3

2:16 p.m.-12:36 a.m.

1 stop10h 20m

Winnipeg

Fri 13/3

7:30 a.m.-10:19 p.m.

1 stop14h 49m

C$ 493

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 27/2

7:30 a.m.-1:26 a.m.

1 stop17h 56m

Winnipeg

Mon 2/3

9:00 p.m.-7:07 p.m.

2 stops22h 07m

C$ 545

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 29/3

6:00 a.m.-3:09 p.m.

1 stop9h 09m

Winnipeg

Sun 5/4

7:30 a.m.-10:21 p.m.

1 stop14h 51m

C$ 555

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/2

Showing 1-10 of 43 results
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Best time to book a flight from Indiana to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Indiana 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 Indiana to Winnipeg
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Indiana 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 Indiana?

    Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Indiana. Winnipeg is conveniently located just 7.3 km from Winnipeg’s city centre.

  • How long is the flight from Indiana to Winnipeg?

    For as low as C$ 769, WestJet can have you in Winnipeg from Indiana in 5h 28m. The distance from Indiana to Winnipeg is about 1506 km. This flight may include one or multiple stops.

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

    The most popular flight routes from Indiana to Winnipeg are Chicago O'Hare Intl - Winnipeg, Chicago Midway - Winnipeg and Cincinnati Cinci./N. Kentucky - Winnipeg.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Indiana 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.

See more FAQs

Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Selkirk
Portage la Prairie

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

Yes, we can. To see specific flights from Indiana to Winnipeg with no change fees, users can toggle flexible booking options after using the search form above to find flights.

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

Yes, Cheapflights offers price alerts on Indiana 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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