Direct 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

Route: Nonstop service available
Distance: 707 miles
Marketing airlines: 5 airlines
Aircraft: 2 aircraft types
Dates: Nov 2, 2026 – Oct 29, 2027

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 2026-11-18, booked with Virgin Australia. This is an observed fare, not a guaranteed price or the lowest price across all dates and programs.

Departure window: 2026-11-12 – 2026-12-11.

ORD → YWGEconomy
UA5475
12,500 points+ $9.00
Departure
2026-11-18
Seats seen
9
Book with
Virgin Australia
Observed (UTC)
2026-11-11 13:02
ORD → YWGEconomy
UA5475
12,500 points+ $9.00
Departure
2026-11-24
Seats seen
9
Book with
Virgin Australia
Observed (UTC)
2026-11-12 03:58
ORD → YWGEconomy
UA5475
12,500 points+ $9.00
Departure
2026-12-03
Seats seen
5
Book with
Virgin Australia
Observed (UTC)
2026-11-10 21:36
ORD → YWGEconomy
UA5475
12,500 points+ $9.00
Departure
2026-12-04
Seats seen
9
Book with
Virgin Australia
Observed (UTC)
2026-11-11 02:38
ORD → YWGEconomy
UA5475
12,500 points+ $9.00
Departure
2026-12-09
Seats seen
9
Book with
Virgin Australia
Observed (UTC)
2026-11-10 17:34
ORD → YWGBusiness
UA5475
25,000 points+ $9.00
Departure
2026-11-24
Seats seen
3
Book with
Virgin Australia
Observed (UTC)
2026-11-12 03:58
ORD → YWGBusiness
UA5475
25,000 points+ $9.00
Departure
2026-12-03
Seats seen
3
Book with
Virgin Australia
Observed (UTC)
2026-11-10 21:36
ORD → YWGBusiness
UA5475
25,000 points+ $9.00
Departure
2026-12-04
Seats seen
4
Book with
Virgin Australia
Observed (UTC)
2026-11-11 02:38
ORD → YWGBusiness
UA5475
25,000 points+ $9.00
Departure
2026-12-09
Seats seen
5
Book with
Virgin Australia
Observed (UTC)
2026-11-10 17:34

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.

Roame's current schedule feed shows nonstop service from ORD to YWG.

Marketing airlines listed in the current schedule, including codeshare sellers, are Air Canada (AC), Avianca (AV), Copa Airlines (CM), Air New Zealand (NZ) and United Airlines (UA). This list does not identify the operating airline for each flight; check the flight details before booking.

Published schedule dates span Nov 2, 2026 – Oct 29, 2027.

Marketing airlines on the Chicago to Winnipeg route

These are marketing airlines, including codeshare sellers. This list does not identify the operating airline for each flight; check the flight details before booking.

Air Canada (AC)Codeshare only
Avianca (AV)Codeshare only
Copa Airlines (CM)Codeshare only
Air New Zealand (NZ)Codeshare only

Airline alliance affiliations represented: Star Alliance

Aircraft flying from ORD to YWG

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.

Are there direct flights from ORD to YWG?

Yes. Roame's current schedule feed shows nonstop service from ORD to YWG.

Which airlines market flights from ORD to YWG?

Which aircraft fly from ORD to YWG?

Aircraft listed in the current schedule include Embraer 175 (long wing) (E7W) and JET.