$141+ Cheap flights from O'Hare Intl (ORD) to Winnipeg (YWG)
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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
Sep 20 — Sep 271
Round-trip
1 adult, Economy
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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 August 21, 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 August 21, 2026.
This Justfly.com deal was found by Cheapflights users on 8/19. 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.
Thu 10/85:30 pm -
1 stop7h 25m
Sun 10/117:00 am -
1 stop9h 40m
Deal found 8/19![WestJet logo]()
$304
This Justfly.com deal was found by Cheapflights users on 8/20. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:30 pm -
1 stop7h 25m
Sat 9/57:00 am -
1 stop9h 40m
Deal found 8/20![WestJet logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/158:04 am -
2 stops16h 51m
Fri 10/237:00 am -
1 stop9h 40m
Deal found 8/17![Multiple Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 8/21. 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
Mon 10/125:00 pm -
2 stops37h 34m
Deal found 8/21![Multiple Airlines logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/115:30 pm -
1 stop7h 25m
Thu 10/227:00 am -
1 stop9h 40m
Deal found 8/17![WestJet logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 10/85:30 pm -
1 stop7h 25m
Mon 10/125:00 pm -
2 stops37h 34m
Deal found 8/21![Multiple Airlines logo]()
$363
This FlightHub deal was found by Cheapflights users on 8/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:30 pm -
1 stop7h 25m
Sat 10/104:55 pm -
1 stop23h 45m
Deal found 8/20![WestJet logo]()
$365
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/185:30 pm -
1 stop7h 25m
Mon 9/216:00 am -
2 stops18h 23m
Deal found 8/19![Multiple Airlines logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/145:30 pm -
1 stop7h 25m
Fri 9/187:55 pm -
2 stops22h 32m
Deal found 8/19![Multiple Airlines logo]()
$370
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 August 21, 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 August 21, 2026.
This Trip.com deal was found by Cheapflights users on 8/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/255:30 pm -
1 stop7h 25m
Sun 9/277:00 am -
1 stop9h 40m
Deal found 8/18![WestJet logo]()
$478
This Porter Airlines deal was found by Cheapflights users on 8/17. 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.
Wed 10/1411:45 am -
1 stop8h 09m
Wed 10/219:20 am -
1 stop6h 59m
Deal found 8/17![Porter Airlines logo]()
$629
This KAYAK deal was found by Cheapflights users on 8/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/811:17 am -
2 stops24h 34m
Fri 9/115:44 pm -
2 stops19h 45m
Deal found 8/20![Delta logo]()
$816
This KAYAK deal was found by Cheapflights users on 8/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/89:15 am -
Nonstop2h 37m
Fri 9/115:00 am -
1 stop6h 21m
Deal found 8/20![Air Canada logo]()
$859
This United Airlines deal was found by Cheapflights users on 8/17. 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.
Thu 10/152:30 pm -
1 stop6h 27m
Sun 10/182:00 pm -
Nonstop2h 35m
Deal found 8/17![United Airlines logo]()
$885
This Porter Airlines deal was found by Cheapflights users on 8/19. 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.
Mon 9/2811:42 am -
1 stop8h 07m
Tue 9/299:20 am -
1 stop10h 10m
Deal found 8/19![Porter Airlines logo]()
$636
This Porter Airlines deal was found by Cheapflights users on 8/17. 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 10/132:50 pm -
1 stop24h 29m
Thu 10/229:20 am -
1 stop6h 59m
Deal found 8/17![Porter Airlines logo]()
$765
This United Airlines deal was found by Cheapflights users on 8/20. 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 10/289:35 am -
Nonstop2h 48m
Mon 11/22:15 pm -
Nonstop2h 35m
Deal found 8/20![United Airlines logo]()
$908
This United Airlines deal was found by Cheapflights users on 8/19. 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.
Thu 10/299:35 am -
Nonstop2h 48m
Sun 11/12:15 pm -
Nonstop2h 35m
Deal found 8/19![United Airlines logo]()
$908
This Porter Airlines deal was found by Cheapflights users on 8/18. 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.
Wed 11/252:50 pm -
1 stop7h 07m
Sun 11/2911:40 am -
2 stops29h 50m
Deal found 8/18![Porter Airlines logo]()
$858
This United Airlines deal was found by Cheapflights users on 8/18. 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 11/259:35 am -
Nonstop2h 48m
Sun 11/292:15 pm -
Nonstop2h 35m
Deal found 8/18![United Airlines logo]()
$908
Last-minute flights from O'Hare Intl to WinnipegDiscover last-minute flight deals from O'Hare Intl to Winnipeg. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Winnipeg. Data last updated August 21, 2026 and is based on user searches.
This Justfly.com deal was found by Cheapflights users on 8/20. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:30 pm -
1 stop7h 25m
Sat 9/57:00 am -
1 stop9h 40m
Deal found 8/20![WestJet logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/145:30 pm -
1 stop7h 25m
Fri 9/187:55 pm -
2 stops22h 32m
Deal found 8/19![Multiple Airlines logo]()
$370
This Priceline deal was found by Cheapflights users on 8/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/145:30 pm -
1 stop7h 25m
Fri 9/186:00 am -
1 stop10h 40m
Deal found 8/19![WestJet logo]()
$376
This Kissandfly.com deal was found by Cheapflights users on 8/17. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:30 pm -
1 stop26h 45m
Sun 9/207:00 am -
1 stop9h 40m
Deal found 8/17![WestJet logo]()
$359
This Mytrip deal was found by Cheapflights users on 8/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:25 am -
1 stop13h 20m
Sun 9/209:05 pm -
2 stops16h 16m
Deal found 8/17![Multiple Airlines logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/185:30 pm -
1 stop7h 25m
Mon 9/216:00 am -
2 stops18h 23m
Deal found 8/19![Multiple Airlines logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/185:30 pm -
1 stop7h 25m
Fri 9/256:00 am -
2 stops18h 23m
Deal found 8/19![Multiple Airlines logo]()
$381
This Mytrip deal was found by Cheapflights users on 8/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:30 pm -
1 stop7h 25m
Sun 9/207:00 am -
2 stops12h 13m
Deal found 8/19![Multiple Airlines logo]()
$408
This Mytrip deal was found by Cheapflights users on 8/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:30 pm -
1 stop7h 25m
Mon 9/285:10 pm -
1 stop15h 50m
Deal found 8/21![Multiple Airlines logo]()
$404
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 August 21, 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 August 21, 2026.
This Trip.com deal was found by Cheapflights users on 8/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:30 pm -
1 stop7h 25m
Deal found 8/16![WestJet logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/185:30 pm -
1 stop7h 25m
Deal found 8/19![WestJet logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/158:04 am -
2 stops16h 51m
Deal found 8/17![Multiple Airlines logo]()
$163
This Trip.com deal was found by Cheapflights users on 8/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/182:15 pm -
1 stop19h 30m
Deal found 8/18![Multiple Airlines logo]()
$171
This Flightnetwork deal was found by Cheapflights users on 8/17. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:30 pm -
1 stop7h 25m
Deal found 8/17![WestJet logo]()
$173
This Trip.com deal was found by Cheapflights users on 8/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:30 pm -
1 stop18h 45m
Deal found 8/17![WestJet logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/138:01 pm -
3 stops23h 59m
Deal found 8/17![Multiple Airlines logo]()
$186
This WestJet deal was found by Cheapflights users on 8/17. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/115:30 pm -
1 stop7h 25m
Deal found 8/17![WestJet logo]()
$189
This WestJet deal was found by Cheapflights users on 8/17. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:30 pm -
1 stop7h 25m
Deal found 8/17![WestJet logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 9/247:28 pm -
3 stops24h 47m
Deal found 8/17![Multiple Airlines logo]()
$194
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 August 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $304 (Justfly.com) |
One-way from | $141 (Trip.com) |
Popular in | February |
Cheapest in | September |
Average price | $801 |
Good round-trip deal | $1,042 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 August 21, 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 9/25
5:30 pm-12:55 am
1 stop7h 25m
Winnipeg
Sun 9/27
7:00 am-4:40 pm
1 stop9h 40m
$478
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 10/14
11:45 am-7:54 pm
1 stop8h 09m
Winnipeg
Wed 10/21
9:20 am-4:19 pm
1 stop6h 59m
$629
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 9/28
11:42 am-7:49 pm
1 stop8h 07m
Winnipeg
Tue 9/29
9:20 am-7:30 pm
1 stop10h 10m
$636
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Tue 10/13
2:50 pm-3:19 pm
1 stop24h 29m
Winnipeg
Thu 10/22
9:20 am-4:19 pm
1 stop6h 59m
$765
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Tue 9/8
11:17 am-11:51 am
2 stops24h 34m
Winnipeg
Fri 9/11
5:44 pm-1:29 pm
2 stops19h 45m
$816
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 11/25
2:50 pm-9:57 pm
1 stop7h 07m
Winnipeg
Sun 11/29
11:40 am-5:30 pm
2 stops29h 50m
$858
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Tue 9/8
9:15 am-11:52 am
Nonstop2h 37m
Winnipeg
Fri 9/11
5:00 am-11:21 am
1 stop6h 21m
$859
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Thu 10/15
2:30 pm-8:57 pm
1 stop6h 27m
Winnipeg
Sun 10/18
2:00 pm-4:35 pm
Nonstop2h 35m
$885
Quickest round-trip
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 10/28
9:35 am-12:23 pm
Nonstop2h 48m
Winnipeg
Mon 11/2
2:15 pm-4:50 pm
Nonstop2h 35m
$908
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Thu 10/29
9:35 am-12:23 pm
Nonstop2h 48m
Winnipeg
Sun 11/1
2:15 pm-4:50 pm
Nonstop2h 35m
$908
Showing 1-10 of 18 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 August.
| 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 August 21, 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 in the morning tend to be the most expensive. A flight at noon could potentially save you up to 43% on airfare.
How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Winnipeg?
Airfare is below average for this route at the moment.
Chicago O'Hare Intl Airport to Winnipeg flights typically cost between $458 and $1,002 in October.The cheapest round-trip price found within the last 5 days was $304 on WestJet (Oct 8-Oct 11).
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 August 21, 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.
Overall
7.4
Crew
8.1
Entertainment
7.1
Comfort
7.3
Boarding
7.7
Food
6.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Overall
7.4
Crew
8.1
Entertainment
7.1
Comfort
7.3
Boarding
7.7
Food
6.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Overall
7.4
Crew
8.1
Entertainment
7.1
Comfort
7.3
Boarding
7.7
Food
6.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl to Winnipeg. 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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O'Hare Intl and Winnipeg flights
Browse other O'Hare Intl and Winnipeg flight options. Last updated on August 21, 2026.
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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 August 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$208 | Average$405 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$362 | Average$762 | FlexibilityNo cancel fee | On-time69% |