Winnipeg (YWG) → Chicago (ORD)
About Winnipeg to Chicago Flights
Discover the best flights from Winnipeg to Chicago, covering 1,138 km in approximately 1h 55m. Winnipeg (YWG) to Chicago (ORD) is one of the busy short-haul routes connecting Canada and United States. With 7 major airlines operating this route including direct flights, travelers have plenty of options to choose from. Whether you're traveling for business or leisure, our comprehensive guide helps you find the best deals, understand seasonal price variations, and choose the right airline for your journey from Winnipeg to Chicago.
12-Month Price History
Flight prices from Winnipeg to Chicago vary significantly throughout the year. February typically offers the best deals with average prices around $305, while July sees the highest prices, averaging $506. Savvy travelers can save up to 40% by choosing their travel dates wisely.
Best Time to Fly
Cheapest Month
February
Save up to 40% on average
Most Expensive
July
Peak season pricing
Book in Advance
149 days
For best prices
Booking Tips
For the best prices on Winnipeg to Chicago flights, we recommend booking 115 days in advance. International flights typically see price increases as the departure date approaches, so early booking is advisable. Tuesday and Wednesday departures often offer the lowest fares, while Friday and Sunday flights tend to be more expensive due to business and leisure travel demand. Consider flying early morning or late evening for additional savings, as these off-peak times usually have lower demand.
Airlines Serving This Route
| Airline | Economy | Business | First |
|---|---|---|---|
Delta Air Lines DL | $280 | $1100 | $1740 |
SkyWest Airlines OO | $280 | $1240 | $1790 |
Kalitta Air K4 | $300 | $1030 | $1530 |
American Airlines AA | $300 | $1210 | $1480 |
United Airlines UA | $310 | $900 | $1850 |
Air France AF | $320 | $1300 | $1870 |
British Airways BA | $370 | $1100 | $1920 |
Delta Air Lines
DL
Economy
$280
Business
$1100
First
$1740
SkyWest Airlines
OO
Economy
$280
Business
$1240
First
$1790
Kalitta Air
K4
Economy
$300
Business
$1030
First
$1530
American Airlines
AA
Economy
$300
Business
$1210
First
$1480
United Airlines
UA
Economy
$310
Business
$900
First
$1850
Air France
AF
Economy
$320
Business
$1300
First
$1870
British Airways
BA
Economy
$370
Business
$1100
First
$1920
Prices shown are estimates based on historical data. Actual prices may vary based on dates, availability, and current promotions.
Alternative Flight Options
Winnipeg → Milwaukee
Winnipeg James Armstrong Richardson International (YWG) to Milwaukee Mitchell International (MKE)
Distance: 1,053 km
Average price: $335
Winnipeg → Chicago
Winnipeg James Armstrong Richardson International (YWG) to Chicago Midway International (MDW)
Distance: 1,163 km
Average price: $357
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Frequently Asked Questions
How long is the flight from Winnipeg to Chicago?
The flight time from Winnipeg (YWG) to Chicago (ORD) is approximately 1 hours and 55 minutes. This duration is for direct flights and may vary depending on aircraft type, weather conditions, and air traffic.
What is the distance between Winnipeg and Chicago?
The aerial distance between Winnipeg and Chicago is 1,138 kilometers (707 miles). This is the straight-line distance, which is used to calculate flight times.
Which airlines fly from Winnipeg to Chicago?
Several airlines operate flights between Winnipeg and Chicago, including American Airlines, United Airlines, SkyWest Airlines and 4 more airlines. Direct flights are available on this route.
What is the cheapest month to fly from Winnipeg to Chicago?
Based on historical data, February typically offers the lowest airfares for flights from Winnipeg to Chicago. However, prices can vary based on holidays, events, and airline promotions. We recommend checking our price calendar for the most up-to-date information.
How far in advance should I book my flight to Chicago?
For the best prices on Winnipeg to Chicago flights, we recommend booking 62 days in advance. International flights generally require earlier booking than domestic routes.
Do I need a visa to travel from Winnipeg to Chicago?
Visa requirements depend on your nationality and the purpose of your visit. Citizens of Canada traveling to United States should check the latest visa requirements. Visit our partner site visarequirements.io for detailed visa information.
What is the time difference between Winnipeg and Chicago?
Winnipeg operates on America/Winnipeg time zone, while Chicago is in the America/Chicago time zone. For current time differences and to plan your schedule, visit our partner site timezig.com for accurate timezone conversions.