Winnipeg (YWG) to Chicago (ORD) flights
An economy award from Winnipeg (YWG) to Chicago (ORD) starts at 10,000 miles one way with Air Canada Aeroplan on United Airlines, plus taxes and fees from $99.99. One airline flies nonstop from Winnipeg (YWG) to Chicago (ORD): United Airlines. The two airports are 706 miles (1,137 km) apart. United Airlines is in Star Alliance. There are also 2 ways to fly it with one stop, through Minneapolis and Toronto.
How many miles YWG to ORD costs
Economy, one way, on the nonstop flights, from the Award Flight Pricer's award charts. Ranges run off-peak to peak; "from" is the floor of a dynamic price.
| Program | Economy | Taxes and fees |
|---|---|---|
| Air Canada AeroplanOn United Airlines | 10,000 | $99.99–119.99 |
| Emirates SkywardsOn United Airlines | 12,000 | $48.59–418.59 |
| Avianca LifeMilesOn United Airlines | 12,500 | $73.59–93.59 |
| ANA Mileage ClubOn United Airlines | 15,000 | $48.59–68.59 |
| Singapore Airlines KrisFlyerOn United Airlines | 15,000 | $48.59–68.59 |
| Thai Royal Orchid PlusOn United Airlines | 17,500 | $48.59–68.59 |
| EVA Air Infinity MileageLandsOn United Airlines | 19,500 | $48.59–68.59 |
| TAP Miles&GoOn United Airlines | 30,000 | $93.39–113.39 |
| Turkish Airlines Miles&SmilesOn United Airlines | 30,000 | $48.59–68.59 |
Business and first class prices are in the Award Flight Pricer. Chart prices need award space on your date, so search it before you transfer points.
Compare every program in the Award Flight PricerAirlines flying nonstop from YWG to ORD
- United AirlinesStar Alliance · bookable with 13 programsWho books it
Book YWG to ORD with points
Loyalty programs that can book at least one of the nonstop airlines, from the Award Booking Guide.
- Air Canada AeroplanBooks United Airlines
- Air New Zealand AirpointsBooks United Airlines
- ANA Mileage ClubBooks United Airlines
- Avianca LifeMilesBooks United Airlines
- Emirates SkywardsBooks United Airlines
- EVA Air Infinity MileageLandsBooks United Airlines
- JetBlue TrueBlueBooks United Airlines
- Lufthansa Miles & MoreBooks United Airlines
- Singapore Airlines KrisFlyerBooks United Airlines
- TAP Miles&GoBooks United Airlines
- Thai Royal Orchid PlusBooks United Airlines
- Turkish Airlines Miles&SmilesBooks United Airlines
- United MileagePlusBooks United Airlines
YWG to ORD with one stop
2 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Minneapolis (MSP)Delta Air Lines the whole way
+1 - Via Toronto (YYZ)Air Canada the whole way
+1
YWG to ORD: common questions
How many miles does YWG to ORD cost?
In economy it starts at 10,000 miles one way with Air Canada Aeroplan on United Airlines, plus taxes and fees from $99.99. Next cheapest: Emirates Skywards (12,000), Avianca LifeMiles (12,500) and ANA Mileage Club (15,000). These are award chart prices from the Award Flight Pricer. Programs that price dynamically can cost more on busy dates, so check yours before you transfer points. Business and first class prices are in the pricer too.
Which airlines fly nonstop from YWG to ORD?
United Airlines (Star Alliance) flies nonstop from Winnipeg (YWG) to Chicago (ORD).
How far is Winnipeg from Chicago by plane?
Winnipeg (YWG) and Chicago (ORD) are 706 miles (1,137 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
Which points programs can book YWG to ORD award flights?
13 programs can book at least one of the nonstop airlines: Air Canada Aeroplan, Air New Zealand Airpoints, ANA Mileage Club, Avianca LifeMiles, Emirates Skywards, EVA Air Infinity MileageLands, JetBlue TrueBlue, Lufthansa Miles & More and 5 more. Which flights each can book depends on its partners, so check the airline before you transfer points.
Where can I connect between Winnipeg and Chicago?
The most direct connections are through Minneapolis (MSP) and Toronto (YYZ). On 2 of them the same airline flies both flights, for example Delta Air Lines through Minneapolis.
More routes
Routes are scheduled nonstop flights. The route data is refreshed monthly; this list was last checked November 11, 2026. Seasonal routes and new launches can be missing or end early, so confirm with the airline before you book. Distances are great-circle, the shortest path between the two airports.