$201+ Cheap flights from Winnipeg (YWG) to O'Hare Intl (ORD)
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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
Nov 12 — Nov 191
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 October 13, 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 October 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 12/147:00 am -
1 stop24h 20m
Sat 1/96:00 am -
2 stops35h 25m
Deal found 10/12![Multiple Airlines logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 12/167:00 am -
1 stop11h 37m
Wed 1/66:00 am -
1 stop8h 40m
Deal found 10/12![Multiple Airlines logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 12/167:00 am -
1 stop11h 37m
Fri 1/86:00 am -
1 stop8h 40m
Deal found 10/12![Multiple Airlines logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 12/119:35 pm -
2 stops21h 02m
Wed 1/66:00 am -
1 stop8h 40m
Deal found 10/12![Multiple Airlines logo]()
$406
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 12/167:00 am -
1 stop11h 37m
Thu 1/76:00 am -
2 stops19h 10m
Deal found 10/12![Multiple Airlines logo]()
$407
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 12/167:00 am -
1 stop11h 37m
Sun 1/106:00 am -
2 stops19h 10m
Deal found 10/12![Multiple Airlines logo]()
$418
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 12/149:35 pm -
2 stops21h 02m
Wed 1/66:00 am -
1 stop8h 40m
Deal found 10/12![Multiple Airlines logo]()
$422
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 12/167:00 am -
1 stop11h 37m
Tue 1/56:00 am -
2 stops19h 10m
Deal found 10/12![Multiple Airlines logo]()
$444
This Mytrip deal was found by Cheapflights users on 10/13. 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 11/209:35 pm -
3 stops27h 08m
Mon 11/235:26 pm -
2 stops23h 59m
Deal found 10/13![Multiple Airlines logo]()
$458
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 October 13, 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 October 13, 2026.
This VIAZA deal was found by Cheapflights users on 10/11. 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 VIAZA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/199:15 am -
1 stop6h 23m
Sun 11/221:55 pm -
1 stop21h 05m
Deal found 10/11![Air Canada logo]()
$467
This Delta deal was found by Cheapflights users on 10/11. 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 2/256:35 am -
2 stops11h 57m
Sun 2/286:00 am -
1 stop6h 50m
Deal found 10/11![Delta logo]()
$575
This Porter Airlines deal was found by Cheapflights users on 10/12. 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 11/107:00 am -
1 stop7h 37m
Tue 11/176:20 pm -
2 stops23h 46m
Deal found 10/12![Porter Airlines logo]()
$594
This Porter Airlines deal was found by Cheapflights users on 10/11. 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 11/97:00 am -
1 stop7h 37m
Mon 11/168:45 pm -
1 stop13h 57m
Deal found 10/11![Porter Airlines logo]()
$603
This Delta deal was found by Cheapflights users on 10/11. 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.
Wed 11/186:35 am -
2 stops9h 43m
Sun 11/226:23 am -
1 stop6h 32m
Deal found 10/11![Delta logo]()
$635
This Air Canada deal was found by Cheapflights users on 10/9. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/188:15 am -
1 stop7h 23m
Sun 11/229:35 am -
Nonstop3h 48m
Deal found 10/9![Air Canada logo]()
$646
This Porter Airlines deal was found by Cheapflights users on 10/13. 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 11/267:00 am -
1 stop7h 36m
Sun 11/2912:15 pm -
2 stops29h 51m
Deal found 10/13![Porter Airlines logo]()
$635
This Delta deal was found by Cheapflights users on 10/12. 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.
Wed 11/186:35 am -
1 stop5h 13m
Fri 11/206:23 am -
1 stop6h 32m
Deal found 10/12![Delta logo]()
$672
This Porter Airlines deal was found by Cheapflights users on 10/13. 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
Thu 11/512:15 pm -
2 stops29h 51m
Deal found 10/13![Porter Airlines logo]()
$652
This Delta deal was found by Cheapflights users on 10/11. 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.
Mon 11/306:32 pm -
1 stop3h 01m
Fri 12/49:59 am -
1 stop7h 35m
Deal found 10/11![Delta logo]()
$672
This Porter Airlines deal was found by Cheapflights users on 10/9. 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 4/57:00 am -
1 stop7h 37m
Sun 4/1112:20 pm -
2 stops29h 50m
Deal found 10/9![Porter Airlines logo]()
$694
This Porter Airlines deal was found by Cheapflights users on 10/11. 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 3/207:00 am -
1 stop7h 37m
Fri 3/268:53 pm -
1 stop25h 04m
Deal found 10/11![Porter Airlines logo]()
$696
Last-minute flights from Winnipeg to O'Hare IntlDiscover last-minute flight deals from Winnipeg to O'Hare Intl. Data last updated October 13, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to O'Hare Intl. Data last updated October 13, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 10/12. 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.
Tue 11/109:35 pm -
2 stops20h 55m
Tue 11/177:35 pm -
2 stops21h 50m
Deal found 10/12![Multiple Airlines logo]()
$504
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 11/119:35 pm -
2 stops21h 10m
Sun 11/156:20 pm -
1 stop15h 55m
Deal found 10/9![Multiple Airlines logo]()
$498
This VIAZA deal was found by Cheapflights users on 10/11. 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 VIAZA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/199:15 am -
1 stop6h 23m
Sun 11/221:55 pm -
1 stop21h 05m
Deal found 10/11![Air Canada logo]()
$467
This Kissandfly.com deal was found by Cheapflights users on 10/9. 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 11/199:35 pm -
2 stops25h 43m
Sun 11/226:20 pm -
2 stops23h 46m
Deal found 10/9![Multiple Airlines logo]()
$511
This Mytrip deal was found by Cheapflights users on 10/13. 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 11/209:35 pm -
3 stops27h 08m
Mon 11/235:26 pm -
2 stops23h 59m
Deal found 10/13![Multiple Airlines logo]()
$458
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 11/277:00 am -
1 stop10h 40m
Wed 12/27:32 pm -
2 stops21h 53m
Deal found 10/9![Multiple Airlines logo]()
$502
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 October 13, 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 October 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 11/189:35 pm -
2 stops26h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 11/99:35 pm -
2 stops20h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$216
This Trip.com deal was found by Cheapflights users on 10/11. 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.
Wed 11/259:35 pm -
2 stops25h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Multiple Airlines logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 12/109:35 pm -
2 stops33h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 12/147:00 am -
1 stop24h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 12/29:35 pm -
2 stops24h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 12/19:35 pm -
2 stops33h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 10/316:00 am -
2 stops12h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Multiple Airlines logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 12/179:35 pm -
2 stops22h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Multiple Airlines logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 10/236:00 am -
1 stop10h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![WestJet logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 11/1610:00 am -
3 stops29h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$272
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 October 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $385 (Kiwi.com) |
One-way from | $201 (Kiwi.com) |
Popular in | October |
Cheapest in | February |
Average price | $881 |
Good round-trip deal | $609 or less |
Good one-way deal | $371 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 October 13, 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
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Mon 11/16
10:00 am-2:31 pm
3 stops29h 31m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$272
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Tue 11/3
7:00 am-1:37 pm
1 stop7h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$273
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Wed 11/4
7:00 am-1:37 pm
1 stop7h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$273
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Tue 11/17
7:00 am-1:37 pm
1 stop7h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$280
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Mon 11/16
6:00 am-1:37 pm
1 stop8h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$290
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Mon 10/26
4:00 pm-12:21 am
2 stops32h 21m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$298
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Wed 11/18
9:35 pm-6:15 pm
3 stops21h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$309
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Fri 12/11
5:24 pm-8:35 pm
1 stop4h 11m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$363
Quickest round-trip
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Fri 10/23
5:40 pm-9:27 pm
1 stop3h 47m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$383
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Thu 11/19
9:15 am-2:38 pm
1 stop6h 23m
Chicago O'Hare Intl
Sun 11/22
1:55 pm-12:00 pm
1 stop21h 05m
$467
Showing 1-10 of 21 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 October 13, 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 October 13, 2026.
See what other customers who have flown with United Airlines and Air Canada 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.
Entertainment
7.1
Boarding
7.7
Crew
8.1
Overall
7.4
Comfort
7.3
Food
6.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Entertainment
7.1
Boarding
7.7
Crew
8.1
Overall
7.4
Comfort
7.3
Food
6.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Entertainment
7.1
Boarding
7.7
Crew
8.1
Overall
7.4
Comfort
7.3
Food
6.7
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
Des Plaines
Glenview
Schaumburg
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Top 2 airlines flying from Winnipeg to O'Hare Intl
Discover the top 2 airlines 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 October 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$517 | Average$702 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$563 | Average$1,130 | FlexibilityNo cancel fee | On-time67% |