$164+ Cheap flights from Winnipeg (YWG) to O'Hare Intl (ORD)
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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Sep 28 — Oct 51
Round-trip
1 adult, Economy
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Find cheap flights from Winnipeg to O'Hare Intl with Cheapflights
1. Tell us where you want to go
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Winnipeg to O'Hare Intl
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Cheapest flights from Winnipeg to O'Hare IntlExplore the most affordable flight options available from Winnipeg to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 29, 2026.
Explore the most affordable flight options available from Winnipeg to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:00 am -
1 stop9h 40m
Thu 9/105:30 pm -
1 stop7h 25m
Deal found 8/25![WestJet logo]()
$288
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 10/227:00 am -
1 stop9h 40m
Fri 10/235:30 pm -
1 stop7h 25m
Deal found 8/26![WestJet logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:00 am -
1 stop9h 40m
Fri 9/115:30 pm -
1 stop7h 25m
Deal found 8/25![WestJet logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:00 am -
1 stop9h 40m
Sun 9/135:30 pm -
1 stop7h 25m
Deal found 8/25![WestJet logo]()
$322
This Trip.com deal was found by Cheapflights users on 8/26. 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.
Sat 9/197:10 pm -
1 stop21h 30m
Mon 9/215:30 pm -
1 stop7h 25m
Deal found 8/26![WestJet logo]()
$329
This Trip.com deal was found by Cheapflights users on 8/28. 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 10/19:05 pm -
1 stop19h 35m
Sun 10/45:30 pm -
1 stop7h 25m
Deal found 8/28![WestJet logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:45 am -
2 stops31h 35m
Fri 9/255:30 pm -
1 stop7h 25m
Deal found 8/25![Multiple Airlines logo]()
$356
This Trip.com deal was found by Cheapflights users on 8/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:20 am -
1 stop6h 58m
Sun 9/275:30 pm -
1 stop7h 25m
Deal found 8/24![Multiple Airlines logo]()
$358
This Trip.com deal was found by Cheapflights users on 8/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/269:20 am -
1 stop6h 58m
Sun 9/275:30 pm -
1 stop7h 25m
Deal found 8/25![Multiple Airlines logo]()
$359
Best flights from Winnipeg to O'Hare IntlDiscover carefully curated flight deals from Winnipeg to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 29, 2026.
Discover carefully curated flight deals from Winnipeg to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 29, 2026.
This Porter Airlines deal was found by Cheapflights users on 8/26. 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 10/209:20 am -
1 stop6h 59m
Wed 10/282:50 pm -
1 stop7h 07m
Deal found 8/26![Porter Airlines logo]()
$486
This oojo deal was found by Cheapflights users on 8/28. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:00 am -
2 stops11h 26m
Sun 10/45:30 pm -
1 stop7h 25m
Deal found 8/28![WestJet logo]()
$549
This Justfly.com deal was found by Cheapflights users on 8/24. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/139:20 am -
1 stop10h 10m
Sun 10/185:30 pm -
1 stop7h 25m
Deal found 8/24![Multiple Airlines logo]()
$604
This Delta deal was found by Cheapflights users on 8/26. 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.
Sat 9/2612:41 pm -
2 stops11h 18m
Wed 9/306:10 am -
1 stop5h 41m
Deal found 8/26![Delta logo]()
$629
This Porter Airlines deal was found by Cheapflights users on 8/26. 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 10/209:20 am -
1 stop6h 59m
Tue 10/272:50 pm -
1 stop7h 07m
Deal found 8/26![Porter Airlines logo]()
$486
This Porter Airlines deal was found by Cheapflights users on 8/24. 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.
Fri 11/207:00 am -
1 stop7h 37m
Sun 11/226:10 pm -
2 stops24h 00m
Deal found 8/24![Porter Airlines logo]()
$522
This Porter Airlines deal was found by Cheapflights users on 8/26. 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.
Sat 9/269:20 am -
1 stop6h 58m
Wed 9/309:45 am -
1 stop10h 09m
Deal found 8/26![Porter Airlines logo]()
$530
This FlightHub deal was found by Cheapflights users on 8/28. 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.
Fri 11/65:00 am -
2 stops31h 13m
Mon 11/97:00 am -
2 stops12h 50m
Deal found 8/28![WestJet logo]()
$642
This FlightHub deal was found by Cheapflights users on 8/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/207:00 am -
1 stop7h 37m
Mon 11/302:50 pm -
1 stop7h 07m
Deal found 8/24![Porter Airlines logo]()
$531
This Porter Airlines deal was found by Cheapflights users on 8/25. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/217:00 am -
1 stop7h 40m
Sun 12/279:45 am -
1 stop25h 00m
Deal found 8/25![Porter Airlines logo]()
$648
Last-minute flights from Winnipeg to O'Hare IntlDiscover last-minute flight deals from Winnipeg to O'Hare Intl. Data last updated August 29, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to O'Hare Intl. Data last updated August 29, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:00 am -
1 stop9h 40m
Thu 9/105:30 pm -
1 stop7h 25m
Deal found 8/25![WestJet logo]()
$288
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:00 am -
1 stop9h 40m
Fri 9/115:30 pm -
1 stop7h 25m
Deal found 8/25![WestJet logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:00 am -
1 stop9h 40m
Sun 9/135:30 pm -
1 stop7h 25m
Deal found 8/25![WestJet logo]()
$322
This FlightHub deal was found by Cheapflights users on 8/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/99:20 am -
1 stop6h 58m
Sun 9/135:30 pm -
1 stop7h 25m
Deal found 8/25![Multiple Airlines logo]()
$362
This Justfly.com deal was found by Cheapflights users on 8/24. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/179:20 am -
1 stop6h 58m
Mon 9/215:30 pm -
1 stop7h 25m
Deal found 8/24![Multiple Airlines logo]()
$365
This Trip.com deal was found by Cheapflights users on 8/26. 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.
Sat 9/197:10 pm -
1 stop21h 30m
Mon 9/215:30 pm -
1 stop7h 25m
Deal found 8/26![WestJet logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:45 am -
2 stops31h 35m
Fri 9/255:30 pm -
1 stop7h 25m
Deal found 8/25![Multiple Airlines logo]()
$356
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:00 am -
2 stops32h 17m
Fri 9/255:30 pm -
1 stop7h 25m
Deal found 8/25![Multiple Airlines logo]()
$371
This Trip.com deal was found by Cheapflights users on 8/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:20 am -
1 stop6h 58m
Sun 9/275:30 pm -
1 stop7h 25m
Deal found 8/24![Multiple Airlines logo]()
$358
This Trip.com deal was found by Cheapflights users on 8/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/269:20 am -
1 stop6h 58m
Sun 9/275:30 pm -
1 stop7h 25m
Deal found 8/25![Multiple Airlines logo]()
$359
This FlightHub deal was found by Cheapflights users on 8/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/309:20 am -
1 stop6h 58m
Tue 10/65:30 pm -
1 stop7h 25m
Deal found 8/24![Multiple Airlines logo]()
$361
One-way flights from Winnipeg to O'Hare IntlSearch for one-way flight options from Winnipeg to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated August 29, 2026.
Search for one-way flight options from Winnipeg to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated August 29, 2026.
This Jetabroad deal was found by Cheapflights users on 8/26. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:00 am -
1 stop9h 40m
Deal found 8/26![WestJet logo]()
$164
This eDestinos deal was found by Cheapflights users on 8/24. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:00 am -
1 stop7h 20m
Deal found 8/24![Porter Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Tue 11/38:35 pm -
3 stops38h 48m
Deal found 8/24![Multiple Airlines logo]()
$200
This Trip.com deal was found by Cheapflights users on 8/26. 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.
Sat 10/102:55 pm -
1 stop25h 45m
Deal found 8/26![WestJet logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Tue 10/279:35 pm -
3 stops37h 48m
Deal found 8/24![Multiple Airlines logo]()
$202
This Kissandfly.com deal was found by Cheapflights users on 8/24. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:00 am -
1 stop7h 20m
Deal found 8/24![Porter Airlines logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Mon 10/197:45 am -
2 stops31h 51m
Deal found 8/24![Multiple Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Sat 10/313:45 pm -
3 stops44h 38m
Deal found 8/24![Multiple Airlines logo]()
$213
This FlightHub deal was found by Cheapflights users on 8/27. 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.
Tue 11/37:00 am -
1 stop7h 37m
Deal found 8/27![Porter Airlines logo]()
$215
This Porter Airlines deal was found by Cheapflights users on 8/25. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/17:00 am -
1 stop7h 37m
Deal found 8/25![Porter Airlines logo]()
$218
Find flight deals from Winnipeg to O'Hare Intl
Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to O'Hare Intl (ORD). 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 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $288 (Kiwi.com) |
One-way from | $164 (Jetabroad) |
Popular in | October |
Cheapest in | February |
Average price | $639 |
Good round-trip deal | $566 or less |
Good one-way deal | $389 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Winnipeg to O'Hare Intl 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 29, 2026.
Use the filters below to find and compare flights from Winnipeg to Chicago O'Hare Intl Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Tue 10/20
9:20 am-4:19 pm
1 stop6h 59m
Chicago O'Hare Intl
Wed 10/28
2:50 pm-9:57 pm
1 stop7h 07m
$486
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Tue 10/20
9:20 am-4:19 pm
1 stop6h 59m
Chicago O'Hare Intl
Tue 10/27
2:50 pm-9:57 pm
1 stop7h 07m
$486
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Fri 11/20
7:00 am-2:37 pm
1 stop7h 37m
Chicago O'Hare Intl
Sun 11/22
6:10 pm-6:10 pm
2 stops24h 00m
$522
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Sat 9/26
9:20 am-4:18 pm
1 stop6h 58m
Chicago O'Hare Intl
Wed 9/30
9:45 am-7:54 pm
1 stop10h 09m
$530
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Fri 11/20
7:00 am-2:37 pm
1 stop7h 37m
Chicago O'Hare Intl
Mon 11/30
2:50 pm-9:57 pm
1 stop7h 07m
$531
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Thu 10/1
7:00 am-6:26 pm
2 stops11h 26m
Chicago O'Hare Intl
Sun 10/4
5:30 pm-12:55 am
1 stop7h 25m
$549
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Tue 10/13
9:20 am-7:30 pm
1 stop10h 10m
Chicago O'Hare Intl
Sun 10/18
5:30 pm-12:55 am
1 stop7h 25m
$604
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Sat 9/26
12:41 pm-11:59 pm
2 stops11h 18m
Chicago O'Hare Intl
Wed 9/30
6:10 am-11:51 am
1 stop5h 41m
$629
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Fri 11/6
5:00 am-12:13 pm
2 stops31h 13m
Chicago O'Hare Intl
Mon 11/9
7:00 am-7:50 pm
2 stops12h 50m
$642
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Mon 12/21
7:00 am-2:40 pm
1 stop7h 40m
Chicago O'Hare Intl
Sun 12/27
9:45 am-10:45 am
1 stop25h 00m
$648
Showing 1-10 of 19 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on Winnipeg-Chicago O'Hare Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Winnipeg-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Winnipeg-Chicago O'Hare Intl Airport 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 Winnipeg-Chicago O'Hare Intl Airport 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 Winnipeg to O'Hare Intl
Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Winnipeg with our price prediction graph.
YWG-ORD
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 Chicago O'Hare Intl Airport
Prices
Airlines
What is the cheapest month to book a flight from Winnipeg to Chicago O'Hare Intl Airport?
Currently, February is the cheapest month in which you can book a flight from Winnipeg to Chicago O'Hare Intl Airport (average of $496). Flying from Winnipeg to Chicago O'Hare Intl Airport in October is currently the most expensive (average of $881). 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 ORD?
Find hourly flight availability from Winnipeg to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 29, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Chicago O'Hare Intl Airport as you normally would.
Reviews of airlines servicing O'Hare Intl
Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated August 29, 2026.
See what other customers who have flown with United Airlines from Winnipeg to Chicago O'Hare Intl Airport have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.7
Overall
7.4
Comfort
7.3
Boarding
7.7
Crew
8.1
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Food
6.7
Overall
7.4
Comfort
7.3
Boarding
7.7
Crew
8.1
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Related info for your journey
Find useful and relevant information for your journey from Winnipeg to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago O'Hare Intl Airport?
Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locationsBenton Harbor
Rosemont
Naperville
Lake Geneva
Schaumburg
Oak Brook
Oakbrook Terrace
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Top airline flying from Winnipeg to O'Hare Intl
Discover the top airline that operate flights from Winnipeg to O'Hare Intl. 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 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$335 | Average$701 | FlexibilityNo cancel fee | On-time69% |