
Book Cheap United flight from Chicago (ORD) to Winnipeg (YWG) from CA $440
Find The Best Day to Book a Cheap United Flights From Chicago to Winnipeg
Cheapest United Flights from Chicago (ORD) to Winnipeg (YWG)
The cheapest flights to Winnipeg James Armstrong Richardson Intl. found within the past 7 days were CA $680 round trip and CA $440 one way. Prices and availability subject to change. Additional terms may apply.
Grab a great United flight from ORD to YWG
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 Chicago to Winnipeg 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 Chicago and Winnipeg
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 Chicago to Winnipeg with United are December.
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 Winnipeg

Victoria Inn Hotel and Convention Centre Winnipeg
The stay was great, the pool was well kept along with fun. The staff were nice too.
Reviewed on Nov 16, 2025

The Grand Winnipeg Airport Hotel by Lakeview
This one is our go to hotel for Winnipeg, whether we are flying or driving to the City. Easily accessible, ample parking, and because it is at the airport, a taxi or Uber is immediately available. Staff are always courteous and helpful, the rooms are spotless and modern, and we are always fully satisfied ...
Reviewed on Nov 17, 2025

Lakeview Signature, Trademark Collection by Wyndham
Quick and the room was clean!
Reviewed on Nov 15, 2025
Want more than a(n) United Flight from Chicago to Winnipeg?
Popular United Flight Routes from ORD
Top United Flight Routes from YWG
Domestic
- Toronto to New York (YYZ - LGA)
- Toronto to Los Angeles (YYZ - LAX)
- Toronto to Manila (YYZ - MNL)
- Toronto to Melbourne (YYZ - MEL)
- Regina to Lagos (YQR - LOS)
- Montreal to Fort Lauderdale (YUL - FLL)
- Toronto to Orlando (YYZ - MCO)
- Phoenix to Manila (PHX - MNL)
- Toronto to Cancun (YYZ - CUN)
- Los Angeles to Toronto (LAX - YYZ)
International
- Toronto to Newark Liberty Intl. Airport (YYZ - EWR)
- Toronto to Las Vegas (YYZ - LAS)
- Regina to Lagos (YQR - LOS)
- Montreal to Fort Lauderdale (YUL - FLL)
- Los Angeles to Toronto (LAX - YYZ)
- Toronto to Orlando (YYZ - MCO)
- Toronto to Delhi (YYZ - DEL)
- Phoenix to Manila (PHX - MNL)
- Vancouver to Delhi (YVR - DEL)
- Vancouver to Seoul (YVR - ICN)
Most Popular
- Best Western Plus Winnipeg Airport Hotel
- Hotels near St. Boniface Hospital
- Hotels in Downtown Winnipeg
- Inn At The Forks
- Victoria Inn Hotel and Convention Centre Winnipeg
- Hotels near Polo Park
- Delta Hotels by Marriott Winnipeg
- Hotels near Outlet Collection Winnipeg
- Hotels near Canada Life Centre
- Sandman Hotel & Suites Winnipeg Airport
- Alt Hotel Winnipeg
- The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel
- Hyatt House Winnipeg-South/Outlet Collection
- Hotels near Unicity Mall
- The Marlborough Hotel
- Birchwood Inn, BW Premier Collection
- Canad Inns Destination Centre Windsor Park
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- Calm Air International Winnipeg (YWG) to Flin Flon (YFO) flights
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- WestJet Brandon (YBR) to Calgary (YYC) flights
- Flights from Vancouver (YVR) to Savoy (CMI)
