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 $310, while July sees the highest prices, averaging $519. 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
168 days
For best prices
Booking Tips
For the best prices on Winnipeg to Chicago flights, we recommend booking 110 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 |
|---|---|---|---|
SkyWest Airlines OO | $510 | $1760 | $3400 |
United Airlines UA | $530 | $2210 | $3300 |
Delta Air Lines DL | $540 | $1800 | $3610 |
American Airlines AA | $540 | $2060 | $3400 |
British Airways BA | $550 | $2310 | $3510 |
Air France AF | $570 | $1890 | $3290 |
Kalitta Air K4 | $630 | $2290 | $3140 |
SkyWest Airlines
OO
Economy
$510
Business
$1760
First
$3400
United Airlines
UA
Economy
$530
Business
$2210
First
$3300
Delta Air Lines
DL
Economy
$540
Business
$1800
First
$3610
American Airlines
AA
Economy
$540
Business
$2060
First
$3400
British Airways
BA
Economy
$550
Business
$2310
First
$3510
Air France
AF
Economy
$570
Business
$1890
First
$3290
Kalitta Air
K4
Economy
$630
Business
$2290
First
$3140
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 78 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.