
Book Cheap United flight from Winnipeg (YWG) to Chicago (ORD)
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Cheapest United Flights from Winnipeg (YWG) to Chicago (ORD)
The cheapest flights to O'Hare Intl. found within the past 7 days were CA $873 round trip and one way. Prices and availability subject to change. Additional terms may apply.
ORD From YWG Economy Coach Packages on Similar Airlines



Frequently asked questions
Grab a great United flight from YWG to ORD
To find a great deal on United flights with Travelocity, simply enter your origin and destination airports, pick your travel dates, and hit search. From here, you can sort by price, flight duration, and arrival/departure time. You can also filter to find nonstop flights.
Flying United Winnipeg to Chicago gives you fights to choose from. With that direct flight time of , you’ll be touching down before you know it.
Find cheap flights with United between Winnipeg and Chicago
United has a range of great fares on stacks of flights, and to find the most affordable for you, there are a few tricks you can try. Booking in advance, for example, is a great way to grab a fantastic deal. Also, choose the cheapest month, if you can. One-way flights from Winnipeg to Chicago with United are .
The more flexible you are, the more affordable flights you’re likely to find. Consider one-way flights and connecting flights, as well as standard roundtrip and direct options. Even if you’re flying today, cheap last-minute flights are easy to find by entering your travel dates and hitting search.
Reasons to book your United flights with Travelocity
Travelocity makes it easy to book a seat, anywhere in the world. The vast inventory, fast search, and advanced filters put some of the best deals on the planet in one place. Whether you’re traveling on business, with friends, family, or on your own, take your pick from some fantastic options. And with free cancellation and pay later options, you can travel more and worry less.
Airport code | Country | Airport name | Number of flights |
|---|---|---|---|
| ORD | USA | O'Hare Intl. | 227 |
| DEN | USA | Denver Intl. | 226 |
| IAH | USA | George Bush Intercontinental | 136 |
| IAD | USA | Washington Dulles Intl. | 100 |
| SFO | USA | San Francisco Intl. | 64 |
| LAX | USA | Los Angeles Intl. | 23 |
| EWR | USA | Liberty Intl. | 20 |
| FRA | DEU | Frankfurt Intl. | 19 |
| NRT | JPN | Narita Intl. | 19 |
| PEK | CHN | Capital Intl. | 16 |
Travelers ❤️ these 🏨 after their flight to Chicago

Hilton Chicago O'Hare Airport
It needs improvement
Reviewed on Oct 28, 2025

Holiday Inn Chicago O'Hare – Rosemont by IHG
Got stuck in Chicago so needed a place to stay. The staff was friendly, they offer a free shuttle service, have a large restaurant on site, and everything was clean. Would recommend!
Reviewed on Oct 27, 2025

Hyatt Regency O'Hare Chicago
The room was exceptionally clean. I loved having a balcony and the bed was fresh and comfortable.
Reviewed on Oct 28, 2025
Want more than a(n) United Flight from Winnipeg to Chicago?
Popular United Flight Routes from YWG
Top United Flight Routes from ORD
Domestic
- Vancouver to Los Angeles (YVR - LAX)
- Vancouver to Bangkok (YVR - BKK)
- Toronto to Manila (YYZ - MNL)
- Halifax to Honolulu (YHZ - HNL)
- Toronto to San José (YYZ - SJO)
- Toronto to Hong Kong (YYZ - HKG)
- Regina to Lagos (YQR - LOS)
- Edmonton to Phoenix (YEG - PHX)
- Edmonton to Delhi (YEG - DEL)
- Toronto to New York (YYZ - LGA)
International
- Regina to Lagos (YQR - LOS)
- Toronto to Bridgetown (YYZ - BGI)
- Vancouver to Tokyo (YVR - NRT)
- Vancouver to Bangkok (YVR - BKK)
- Toronto to Manila (YYZ - MNL)
- Vancouver to Manila (YVR - MNL)
- Edmonton to Phoenix (YEG - PHX)
- Toronto to Delhi (YYZ - DEL)
- Toronto to Hong Kong (YYZ - HKG)
- Vancouver to Tokyo (YVR - NRT)
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