Flights from Chicago to Winnipeg

Did you mean Flights from Winnipeg to Chicago?

Chicago

United States

ORD

Chicago O'Hare International Airport

Winnipeg

Canada

YWG

Winnipeg / James Armstrong Richardson International Airport

Distance: 707 miles

Observed award fares

A sample of one-way prices for one traveler from Roame’s fare cache. Points, fees, and seats describe the same observation. Availability can change; confirm with the loyalty program before transferring points.

Lowest price in this limited sample: 12,500 points + $9.00 for ORD → YWG, Economy, on 2026-10-17, booked with Virgin Australia. This is an observed fare, not a guaranteed price or the lowest price across all dates and programs.

Departure window: 2026-10-17 through 2026-11-15.

Recently observed award prices by route, flight, departure date, cabin, and booking program
Route / flight	Departure	Cabin	Book with	Points	Fees (USD)	Seats seen	Observed (UTC)
ORD → YWG UA5216	2026-10-17	Economy	Virgin Australia	12,500	$9.00	9	2026-10-16 16:03
ORD → YWG UA5252	2026-10-17	Economy	Virgin Australia	12,500	$9.00	9	2026-10-16 16:03
ORD → YWG UA5216	2026-10-18	Economy	Virgin Australia	12,500	$9.00	9	2026-10-17 07:10
ORD → YWG UA5216	2026-10-19	Economy	Virgin Australia	12,500	$9.00	3	2026-10-17 03:52
ORD → YWG UA5216	2026-10-20	Economy	Virgin Australia	12,500	$9.00	9	2026-10-17 04:58
ORD → YWG UA5475	2026-10-27	Economy	Virgin Australia	12,500	$9.00	9	2026-10-17 03:59
ORD → YWG UA5475	2026-11-04	Economy	Virgin Australia	12,500	$9.00	9	2026-10-15 23:28
ORD → YWG UA5475	2026-11-11	Economy	Virgin Australia	12,500	$9.00	9	2026-10-17 02:57
ORD → YWG UA5252	2026-10-17	Business	Virgin Australia	25,000	$9.00	3	2026-10-16 16:03
ORD → YWG UA5216	2026-10-17	Business	Virgin Australia	25,000	$9.00	2	2026-10-16 16:03
ORD → YWG UA5475	2026-11-11	Business	Virgin Australia	25,000	$9.00	1	2026-10-17 02:57

Chicago to Winnipeg route overview

Chicago O'Hare International Airport (ORD) serves Chicago; Winnipeg / James Armstrong Richardson International Airport (YWG) serves Winnipeg.

The airports are 707 miles apart by great-circle distance.

Frequently asked questions

Which airports serve the Chicago to Winnipeg route?

Chicago O'Hare International Airport (ORD) is the origin airport and Winnipeg / James Armstrong Richardson International Airport (YWG) is the destination airport.

How far is Winnipeg from Chicago?

ORD and YWG are approximately 707 miles apart by great-circle distance.

More routes from Chicago

Published schedules are temporarily unavailable for ORD. Airport facts and route navigation remain available.