$166+ Cheap flights from O'Hare Intl (ORD) to Winnipeg (YWG)
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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
Oct 25 — Nov 11
Round-trip
1 adult, Economy
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from O'Hare Intl to WinnipegExplore the most affordable flight options available from O'Hare Intl to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 25, 2026.
Explore the most affordable flight options available from O'Hare Intl to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:30 pm -
1 stop7h 25m
Mon 10/269:35 pm -
2 stops14h 05m
Deal found 9/21![Multiple Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:30 pm -
1 stop7h 25m
Thu 10/297:00 am -
1 stop10h 40m
Deal found 9/21![Multiple Airlines logo]()
$365
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:20 pm -
1 stop14h 55m
Mon 11/166:55 pm -
1 stop16h 45m
Deal found 9/23![Multiple Airlines logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:30 pm -
1 stop7h 25m
Tue 10/279:35 pm -
2 stops15h 16m
Deal found 9/21![Multiple Airlines logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:30 pm -
1 stop7h 25m
Sat 10/316:00 am -
2 stops12h 16m
Deal found 9/23![Multiple Airlines logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:30 pm -
1 stop7h 25m
Fri 10/309:35 pm -
2 stops15h 16m
Deal found 9/23![Multiple Airlines logo]()
$386
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:30 pm -
1 stop7h 25m
Sun 11/18:35 pm -
2 stops22h 10m
Deal found 9/23![Multiple Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:30 pm -
2 stops16h 05m
Tue 10/275:00 am -
1 stop12h 40m
Deal found 9/21![Multiple Airlines logo]()
$395
This Lucky2Go deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Lucky2Go is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:20 pm -
1 stop14h 55m
Sun 11/86:55 pm -
1 stop22h 45m
Deal found 9/23![Multiple Airlines logo]()
$406
Best flights from O'Hare Intl to WinnipegDiscover carefully curated flight deals from O'Hare Intl to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 25, 2026.
Discover carefully curated flight deals from O'Hare Intl to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:00 am -
2 stops14h 00m
Mon 10/197:00 am -
1 stop9h 40m
Deal found 9/20![Multiple Airlines logo]()
$561
This Justfly.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:20 pm -
2 stops23h 50m
Mon 11/27:00 am -
1 stop7h 37m
Deal found 9/25![Porter Airlines logo]()
$621
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:04 am -
2 stops8h 30m
Tue 12/86:25 am -
2 stops9h 52m
Deal found 9/22![Delta logo]()
$767
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/42:20 pm -
2 stops23h 49m
Mon 12/712:45 pm -
2 stops22h 40m
Deal found 9/20![United Airlines logo]()
$792
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/275:26 pm -
2 stops22h 59m
Mon 11/304:00 pm -
1 stop13h 10m
Deal found 9/20![Multiple Airlines logo]()
$621
This Porter Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:20 pm -
2 stops23h 50m
Sat 11/287:00 am -
1 stop7h 46m
Deal found 9/21![Porter Airlines logo]()
$666
This Porter Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/122:50 pm -
1 stop7h 07m
Mon 11/167:00 am -
1 stop7h 37m
Deal found 9/24![Porter Airlines logo]()
$683
This United Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:29 am -
Nonstop2h 54m
Mon 11/22:15 pm -
Nonstop2h 35m
Deal found 9/23![United Airlines logo]()
$884
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/247:45 pm -
Nonstop2h 48m
Mon 2/17:00 am -
Nonstop2h 45m
Deal found 9/22![United Airlines logo]()
$886
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:35 am -
Nonstop2h 48m
Sat 11/282:15 pm -
Nonstop2h 35m
Deal found 9/21![United Airlines logo]()
$886
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/119:35 am -
Nonstop2h 48m
Mon 11/162:15 pm -
Nonstop2h 35m
Deal found 9/20![United Airlines logo]()
$886
Last-minute flights from O'Hare Intl to WinnipegDiscover last-minute flight deals from O'Hare Intl to Winnipeg. Data last updated September 25, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Winnipeg. Data last updated September 25, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:30 pm -
1 stop7h 25m
Tue 10/279:35 pm -
2 stops15h 16m
Deal found 9/21![Multiple Airlines logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:30 pm -
1 stop7h 25m
Sat 10/316:00 am -
2 stops12h 16m
Deal found 9/23![Multiple Airlines logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:30 pm -
1 stop7h 25m
Fri 10/309:35 pm -
2 stops15h 16m
Deal found 9/23![Multiple Airlines logo]()
$386
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:30 pm -
1 stop7h 25m
Sun 11/18:35 pm -
2 stops22h 10m
Deal found 9/23![Multiple Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:30 pm -
1 stop7h 25m
Mon 10/269:35 pm -
2 stops14h 05m
Deal found 9/21![Multiple Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:30 pm -
1 stop7h 25m
Thu 10/297:00 am -
1 stop10h 40m
Deal found 9/21![Multiple Airlines logo]()
$365
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:30 pm -
2 stops16h 05m
Tue 10/275:00 am -
1 stop12h 40m
Deal found 9/21![Multiple Airlines logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:30 pm -
1 stop17h 40m
Fri 10/309:35 pm -
2 stops15h 16m
Deal found 9/22![Multiple Airlines logo]()
$416
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:30 pm -
1 stop17h 40m
Sat 10/316:00 am -
2 stops12h 16m
Deal found 9/23![Multiple Airlines logo]()
$417
One-way flights from O'Hare Intl to WinnipegSearch for one-way flight options from O'Hare Intl to Winnipeg. Find affordable one-way fares based on user searches. Data last updated September 25, 2026.
Search for one-way flight options from O'Hare Intl to Winnipeg. Find affordable one-way fares based on user searches. Data last updated September 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:20 pm -
2 stops23h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Porter Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:30 pm -
1 stop7h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![WestJet logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:20 pm -
1 stop25h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/612:20 pm -
2 stops28h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:20 pm -
1 stop16h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:50 pm -
2 stops29h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:50 pm -
2 stops21h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:20 pm -
2 stops23h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Porter Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:15 am -
2 stops16h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Multiple Airlines logo]()
$203
Find flight deals from O'Hare Intl to Winnipeg
Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) 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 September 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $361 (Kiwi.com) |
One-way from | $166 (Kiwi.com) |
Popular in | September |
Cheapest in | June |
Average price | $1,133 |
Good round-trip deal | $876 or less |
Good one-way deal | $337 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl 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 7,457,451 searches. Data last updated September 25, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Winnipeg that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Fri 10/30
7:50 pm-1:10 am
2 stops29h 20m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$189
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 10/28
7:28 pm-1:10 am
2 stops29h 42m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$199
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Fri 11/6
6:20 pm-6:10 pm
2 stops23h 50m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$202
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 10/14
8:30 am-12:55 am
3 stops40h 25m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$222
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Tue 10/27
2:11 pm-1:10 am
3 stops34h 59m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$224
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 11/30
7:55 am-4:25 pm
2 stops32h 30m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$228
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Fri 11/6
6:00 am-11:05 am
3 stops29h 05m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$250
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Sat 11/7
8:13 pm-4:25 pm
3 stops44h 12m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$264
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 10/28
4:30 pm-11:59 pm
1 stop7h 29m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$268
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Sun 10/11
6:00 am-8:00 pm
2 stops14h 00m
Winnipeg
Mon 10/19
7:00 am-4:40 pm
1 stop9h 40m
$561
Showing 1-10 of 20 resultsSorted by cheapest first
Compare providers for flights from O'Hare Intl to Winnipeg
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from O'Hare Intl to Winnipeg in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago O'Hare Intl Airport-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Winnipeg flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago O'Hare Intl Airport-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from O'Hare Intl to Winnipeg
Have a flexible travel schedule? Discover the best time to fly to Winnipeg from O'Hare Intl with our price prediction graph.
ORD-YWG
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 Chicago O'Hare Intl Airport to Winnipeg
Prices
Airlines
What is the cheapest time of day to fly from ORD to YWG?
Find hourly flight availability from O'Hare Intl to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 25, 2026.
One of the essential ways to save on airfare from Chicago O'Hare Intl Airport to Winnipeg is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 51% on airfare.
How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Winnipeg?
Airfare is typical for this route at the moment.
Chicago O'Hare Intl Airport to Winnipeg flights typically cost between $252 and $1,106 in October.The cheapest round-trip price found within the last 5 days was $361 on Multiple Airlines (Oct 22-Oct 26).
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 September 25, 2026.
Get a feel of what it's like to fly with United Airlines and WestJet from Chicago O'Hare Intl Airport to Winnipeg by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.1
Food
6.7
Comfort
7.3
Crew
8.1
Overall
7.4
Boarding
7.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Entertainment
7.1
Food
6.7
Comfort
7.3
Crew
8.1
Overall
7.4
Boarding
7.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Entertainment
7.1
Food
6.7
Comfort
7.3
Crew
8.1
Overall
7.4
Boarding
7.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
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O'Hare Intl and Winnipeg flights
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Top 2 airlines flying from O'Hare Intl to Winnipeg
Discover the top 2 airlines that operate flights from O'Hare Intl to Winnipeg. 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 7,457,451 searches. Data last updated September 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$222 | Average$454 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$362 | Average$762 | FlexibilityNo cancel fee | On-time69% |