Flights from Winnipeg (YWG) to Chicago (ORD)

Flight Winnipeg(YWG) to Chicago(ORD)
CHANGE DIRECTION

Winnipeg James Armstrong Richardson International Airport O'Hare International Airport
YWG : Winnipeg , Canada ORD : Chicago , United States
UTC-5(DST) UTC-5(DST)

Winnipeg to Chicago Flights

Find updated flight schedules, timetable, distance, aircraft types, Map, Transfer for routes from Winnipeg (YWG) to Chicago (ORD).

Change Direction(ORD to YWG)

Flight Schedules Winnipeg to Chicago

This route is operated by United Airlines. This is the first direct flight from Winnipeg to Chicago.

Change Direction(ORD to YWG)

Flight Duration: Approximately 2 hours 21 minutes to 2 hours 43 minutes (Direct Flights)

Flight No. Departure Time Arrival Time Duration Airfare
UA5389 07:00 09:31 2h31m Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
Flight schedules as of September 01, 2025, 06:03 AM(OAG data). Schedules may change without notice, so please check with airlines before booking. Refer to FlyTeam's terms of use before proceeding. Some airlines and flight numbers may not be displayed.

The last direct flight from Winnipeg to Chicago is the final flight at 14:20 by United Airlines UA5639.

From Winnipeg (YWG) to Chicago (ORD) Flights Info

Duration(Flight time)

From Winnipeg to Chicago
2 hours 21 minutes to 2 hours 43 minutes
From Chicago to Winnipeg
2 hours 24 minutes to 2 hours 47 minutes

Distance

From Chicago to Winnipeg
Approx. 710 miles
Approx. 1,140 Km
This is different from mileage credits in airline loyalty programs.

Winnipeg to Chicago Map

Winnipeg James Armstrong Richardson International Airport Winnipeg James Armstrong Richardson International Airport
O'Hare International Airport O'Hare International Airport

Type of aircraft (YWG to ORD)

Below is a list of the aircraft types and airlines operating on this route. (Direct flights only)

* All links below lead to Japanese pages.

Transfer / Cities with One-Stop Flights

This list shows cities where you can connect for one-stop flights between Winnipeg and Chicago. Direct flights operate on each segment, with the shortest flight durations listed. This is a great resource for travelers planning multi-city itineraries.

Minneapolis (MSP)
YWG 1h30m MSP 1h19m ORD
1h27m 1h22m
Pearson (YYZ)
YWG 2h25m YYZ 1h47m ORD
2h27m 1h30m

FAQ : Winnipeg to Chicago

How far is it from Winnipeg to Chicago?
The distance between Winnipeg (YWG) to Chicago (ORD) is approximately 710 miles(1,140km) by air.
Which airlines operate at from Winnipeg(YWG) to Chicago(ORD)?
Currently, this route is served by United Airlines (Japanese). You can check flight schedules for this route at Winnipeg to Chicago Flight Schedules and Chicago to Winnipeg Flight Schedules
What aircraft types are flying on the Winnipeg (YWG) to Chicago (ORD) route?
The Winnipeg – Chicago route is operated by Embraer 175 aircraft types.
What is the time difference between Winnipeg to Chicago?
There is no time difference between Winnipeg James Armstrong Richardson International Airport(Winnipeg) and O'Hare International Airport(Chicago).Winnipeg is currently observing daylight saving time (DST) from March 9, 2025 to November 2, 2025.Chicago is currently observing daylight saving time (DST) from March 9, 2025 to November 2, 2025.