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Route

Winnipeg → Chicago

YWGWinnipegWinnipeg / James Armstrong Richardson International Airport
ORDChicagoChicago O'Hare International Airport
Distance
707 mi
Estimated flight time
~1h 55m

Same local time in Winnipeg and Chicago.

Observed nonstop

View the reverse route

How often does this route fly?

Frequency

Daily at most

On average around 1 flights a day, observed from October 2025 to September 2026.

1
flights per day
2
busiest month · Oct
1
quietest month · Nov
1 hr 47 min
measured flight time
12 / 12
months seen

Through the year

Per day, month by month

  1. 1Jan2026
  2. 1Feb
  3. 1Mar
  4. 1Apr
  5. 1May
  6. 2Jun
  7. 2Jul
  8. 2Aug
  9. 2Sep
  10. 2Oct2025
  11. 1Nov
  12. 1Dec

Airlines

Who flies it

SkyWest Airlinesall year

Through the day

Departure times

Local time in Winnipeg. Most departures between 13:00 and 16:00.

  1. 00:00
  2. 01:00
  3. 02:00
  4. 03:00
  5. 04:00
  6. 05:00
  7. 06:00
  8. 07:00
  9. 08:00
  10. 09:00
  11. 10:00
  12. 11:00
  13. 12:00
  14. 13:00
  15. 14:00
  16. 15:00
  17. 16:00
  18. 17:00
  19. 18:00
  20. 19:00
  21. 20:00
  22. 21:00
  23. 22:00
  24. 23:00

Through the week

By weekday

  1. 1.4Mon
  2. 1.3Tue
  3. 1.4Wed
  4. 1.4Thu
  5. 1.4Fri
  6. 1.4Sat
  7. 1.5Sun

Fleet

Aircraft observed

  1. Embraer 175E75L99%
  2. Cessna Citation LatitudeC68A0%
All the numbers in a table
MonthPer daySeenAirlines
January 2026131
  • SkyWest Airlines30×
February 2026130
  • SkyWest Airlines30×
March 2026128
  • SkyWest Airlines27×
April 2026129
  • SkyWest Airlines28×
May 2026140
  • SkyWest Airlines40×
June 2026259
  • SkyWest Airlines57×
July 2026259
  • SkyWest Airlines58×
August 2026257
  • SkyWest Airlines56×
September 2026262
  • SkyWest Airlines59×
October 2025255
  • SkyWest Airlines55×
November 2025129
  • SkyWest Airlines29×
December 2025129
  • SkyWest Airlines29×

Airlines observed on this route

From observed callsign routes on YWG-ORD - not a booking guarantee.

SkyWest Airlines

OO · SKW

Hub: ORD Chicago

249 departure airportsView airline →

About this route

  • International route: Winnipeg and Chicago are in different countries.
  • The opposite direction has also been observed as a direct connection.
  • Direct destinations observed from Winnipeg: 37.
  • Direct destinations observed from Chicago: 259.

The airports on this route

Winnipeg / James Armstrong Richardson International Airport

Winnipeg, CanadaYWG / CYWG

Major airport · 37 direct destinations · 2 runways · longest runway 11,001 ft

34 °F · CloudySource: METAR observation via the NOAA Aviation Weather Center

Airport pageAll direct destinations

Chicago O'Hare International Airport

Chicago, United StatesORD / KORD

International hub · 259 direct destinations · 8 runways · longest runway 12,999 ft

51 °F · CloudySource: METAR observation via the NOAA Aviation Weather Center

Airport pageAll direct destinations

About the route from Winnipeg to Chicago

The observed direct connection between Winnipeg / James Armstrong Richardson International Airport (YWG) and Chicago O'Hare International Airport (ORD) covers approximately 707 mi. The estimated flight time is around 1h 55m. SkyWest Airlines has been observed on this connection in the available route data.

Frequently asked questions about this route

How far is Winnipeg from Chicago by air?
The great-circle distance between Winnipeg / James Armstrong Richardson International Airport and Chicago O'Hare International Airport is approximately 707 mi.
How long is the flight from Winnipeg to Chicago?
Based on the distance, the estimated flight time is about 1h 55m. This is an estimate, not a schedule.
Is there a direct connection from Winnipeg to Chicago?
Yes, a direct connection between YWG and ORD has been observed in our route data.
Which airlines have been observed on this route?
In the available route data: SkyWest Airlines.
How often is there a flight from Winnipeg to Chicago?
On average around 1 flights a day, measured over twelve months (October 2025 to September 2026) in the flight archive, with 508 observed flights. Mainly SkyWest Airlines. That is an observation, not a timetable.
What is the current time difference between Winnipeg and Chicago?
Same local time in Winnipeg and Chicago.

Where this data comes from

The route data comes from the flight archive (ADS-B, adsb.lol): which connections actually flew over the last twelve full months and who flew them, combined with our own airport, runway, and airline datasets. It is reference data about observed routes - not a current timetable and no claim about bookability.

The frequency and aircraft on this page come from the flight archive (ADS-B, 12 months, October 2025 to September 2026), summarized per route per month. We do not see every flight, so it is a floor, not a count.

Route data updated on October 11, 2026.