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Cheap flights from Winnipeg to Indiana from C$ 155
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 17/10. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — IND
15 Oct — 22 Oct1
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 15 September 2025.
Find flight deals from Winnipeg to Indiana
Cheapest flights from Winnipeg to IndianaExplore 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 15 September 2025.
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 15 September 2025.
Fri 17/108:30 a.m.YWG - ORD
1 stop8h 13mWestJet
Sun 19/105:30 p.m.ORD - YWG
1 stop15h 31mWestJet
Deal found 14/9C$ 270
Fri 17/109:00 a.m.YWG - MDW
1 stop14h 46mMultiple Airlines
Wed 29/102:06 p.m.MDW - YWG
2 stops34h 35mMultiple Airlines
Deal found 14/9C$ 295
Thu 16/109:05 p.m.YWG - ORD
1 stop19h 38mWestJet
Sun 26/102:20 p.m.ORD - YWG
1 stop10h 21mWestJet
Deal found 14/9C$ 302
Thu 30/109:00 p.m.YWG - ORD
1 stop16h 35mMultiple Airlines
Sat 1/116:00 a.m.ORD - YWG
2 stops18h 41mMultiple Airlines
Deal found 12/9C$ 332
Thu 16/109:00 a.m.YWG - MDW
1 stop14h 46mMultiple Airlines
Sun 26/106:20 a.m.MDW - YWG
1 stop8h 47mMultiple Airlines
Deal found 14/9C$ 338
Mon 27/106:15 a.m.YWG - ORD
1 stop7h 20mMultiple Airlines
Thu 20/116:35 p.m.ORD - YWG
1 stop20h 32mMultiple Airlines
Deal found 14/9C$ 338
Fri 3/105:30 p.m.YWG - ORD
2 stops19h 09mWestJet
Sun 5/105:30 p.m.ORD - YWG
1 stop15h 31mWestJet
Deal found 13/9C$ 340
Fri 17/108:30 a.m.YWG - ORD
1 stop8h 13mMultiple Airlines
Wed 29/107:43 p.m.ORD - YWG
2 stops23h 29mMultiple Airlines
Deal found 14/9C$ 375
Wed 29/107:30 a.m.YWG - ORD
1 stop27h 11mMultiple Airlines
Wed 5/1112:37 p.m.ORD - YWG
2 stops36h 04mMultiple Airlines
Deal found 14/9C$ 378
Thu 9/109:00 a.m.YWG - MDW
1 stop14h 46mMultiple Airlines
Sun 12/106:20 a.m.MDW - YWG
2 stops18h 10mMultiple Airlines
Deal found 13/9C$ 382
Wed 29/104:55 p.m.YWG - MDW
1 stop23h 58mMultiple Airlines
Wed 5/112:06 p.m.MDW - YWG
2 stops34h 35mMultiple Airlines
Deal found 13/9C$ 389
Fri 17/109:00 a.m.YWG - MDW
1 stop14h 46mMultiple Airlines
Sun 19/106:20 a.m.MDW - YWG
2 stops18h 10mMultiple Airlines
Deal found 14/9C$ 400
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 15 September 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 17/10
8:30 a.m.-4:43 p.m.
1 stop8h 13m
Chicago O'Hare Intl
Sun 19/10
5:30 p.m.-11:10 p.m.
1 stop29h 40m
C$ 282
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Thu 16/10
9:05 p.m.-4:43 p.m.
1 stop19h 38m
Chicago O'Hare Intl
Sun 26/10
2:20 p.m.-12:41 a.m.
1 stop10h 21m
C$ 302
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Mon 27/10
6:15 a.m.-1:35 p.m.
1 stop7h 20m
Chicago O'Hare Intl
Thu 20/11
6:35 p.m.-3:07 p.m.
1 stop20h 32m
C$ 338
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Fri 3/10
5:30 p.m.-12:39 p.m.
2 stops19h 09m
Chicago O'Hare Intl
Sun 5/10
5:30 p.m.-9:01 a.m.
1 stop15h 31m
C$ 340
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Thu 16/10
9:00 a.m.-11:46 p.m.
1 stop14h 46m
Chicago Midway
Sun 26/10
9:26 p.m.-12:39 a.m.
2 stops27h 13m
C$ 368
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Thu 9/10
9:00 a.m.-11:46 p.m.
1 stop14h 46m
Chicago Midway
Sun 12/10
6:20 a.m.-12:30 a.m.
2 stops18h 10m
C$ 382
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Wed 29/10
4:55 p.m.-4:53 p.m.
1 stop23h 58m
Chicago Midway
Wed 5/11
2:06 p.m.-12:41 a.m.
2 stops34h 35m
C$ 389
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Fri 17/10
9:00 a.m.-11:46 p.m.
1 stop14h 46m
Chicago Midway
Sun 19/10
6:20 a.m.-12:30 a.m.
2 stops18h 10m
C$ 400
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Thu 30/10
7:30 a.m.-10:03 p.m.
2 stops14h 33m
Chicago Midway
Sat 1/11
1:37 p.m.-4:07 p.m.
1 stop26h 30m
C$ 419
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Fri 17/10
9:15 p.m.-4:43 p.m.
2 stops19h 28m
Chicago O'Hare Intl
Sun 19/10
5:30 p.m.-5:25 p.m.
3 stops23h 55m
C$ 462
Showing 1-10 of 41 results
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, January is the cheapest month in which you can book a flight from Winnipeg to Indiana (average of C$ 414). Flying from Winnipeg to Indiana in July is currently the most expensive (average of C$ 510). 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 15 September 2025.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Indiana as you normally would.
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 15 September 2025.
Check out reviews from past customers who have flown with United Airlines,WestJet, andAir 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.
Entertainment
7.1
Crew
8.1
Boarding
7.7
Comfort
7.3
Overall
7.4
Food
6.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Sep 2025
FRA - SFO
Entertainment
7.1
Crew
8.1
Boarding
7.7
Comfort
7.3
Overall
7.4
Food
6.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Sep 2025
FRA - SFO
Entertainment
7.1
Crew
8.1
Boarding
7.7
Comfort
7.3
Overall
7.4
Food
6.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Sep 2025
FRA - SFO
Entertainment
7.1
Crew
8.1
Boarding
7.7
Comfort
7.3
Overall
7.4
Food
6.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Sep 2025
FRA - SFO
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.
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Alternative routes for Winnipeg to Indiana
See prices for flight routes from nearby airports that may be better suited for you.
Top 3 airlines flying from Winnipeg to Indiana
Discover the top 3 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 15 September 2025.
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How does Cheapflights help users find flights from Winnipeg to Indiana?
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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.
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