Cheap flights from Chicago to Winnipeg

Flight deals from Chicago to Winnipeg

Below you can see the best deals on flights Chicago — Winnipeg for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 18 September, from $156.

Top 10 cheap flights from Chicago to Winnipeg

About the Chicago — Winnipeg flight

Looking for cheap flights from Chicago to Winnipeg? Compare fares from different airlines, check the flight schedule and travel time — and book your Chicago — Winnipeg ticket online at the best price.

The route has direct flights — around 28 flights per week, flights are operated by United Airlines, Air Canada, a nonstop flight takes about 2 h 38 min, the distance between the cities is around 1,155 km.

Planning your trip? You may find our Winnipeg travel guide, how to get from the airport into town and Winnipeg weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

from $156Min. price

SeptemberCheapest

AprilPeak season

YesDirect flights

1,155 kmDistance

2 h 38 minTravel time

2Airlines

28 / wkFlights

Flight schedule from Chicago to Winnipeg

The table shows direct flights from Chicago to Winnipeg on the selected date. The flight takes approximately 2 h 38 min. Regular flights are operated by United Airlines and Air Canada. Departures from O'Hare International Airport, Chicago Midway International Airport and Midway International Airport airports, arrivals at Winnipeg James Armstrong Richardson International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

Today

Any time

Last update: 07 Sep 2026

Airline

Flight

Departure

Arrival

Duration

Days

Status

Below is a calendar of the lowest flight ticket prices for Chicago — Winnipeg by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $156 in September, and the most expensive are around $347 in April. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

Prices by month

Average one-way fares from Chicago to Winnipeg by month. Tickets are usually cheapest in January (around $221) and priciest in July (about $338) — use the table and chart below to pick the best time to fly.

Month	Average price	Level	Month	Average price	Level	Month	Average price	Level
Jan	$221	low	May	$291	high	Sep	$280	medium
Feb	$233	low	Jun	$315	high	Oct	$233	low
Mar	$256	medium	Jul	$338	high	Nov	$268	medium
Apr	$268	medium	Aug	$326	high	Dec	$315	high

Some values are estimated based on seasonality.

When to fly

Weather in Winnipeg: it is warmest in July (up to 27 °C on average) and coolest in January (around -9 °C). The driest month is January.

Tickets are usually cheapest in September and most expensive in April. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Winnipeg

Dry and wet days · Winnipeg

Wind speed and direction · Winnipeg

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How to get the best deal on a Chicago — Winnipeg ticket

Book ahead: fares for Chicago — Winnipeg are usually lower 3–8 weeks before departure than at the last minute.
Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
Chicago is served by more than one airport — compare fares and travel time to each before you book.
The cheapest month to fly to Winnipeg is usually September — plan your trip around it if your dates are flexible.
Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Flights on the Chicago — Winnipeg route are operated by 2 airlines; United Airlines runs the most flights (around 86% of all flights). Compare carriers, flight shares and schedules below.

United AirlinesUA
8x/week
WebsiteFleet: 956165M pax/year
- Direct flight ORD → YWG8x/week
  Duration
  2h 35m
  Days
  MTWTFSS
85.7%Open →
Air CanadaAC
1x/week
WebsiteFleet: 20346M pax/year
- Direct flight ORD → YWG1x/week
14.3%Open →

Cities and airports on the Chicago — Winnipeg route

Flights Chicago — Winnipeg depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport and arrive at Winnipeg James Armstrong Richardson International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Chicago

CHI

United States

About the city How to get there Weather All about the country United States

Arrival

Winnipeg

YWG

Canada

About the city How to get there Weather All about the country Canada

Departure airports

O'Hare International AirportORD
About the airport
Chicago Midway International AirportMDW
About the airport
Midway International AirportNOH
About the airport
Chicago Rockford International AirportRFD
About the airport

Arrival airports

Winnipeg James Armstrong Richardson International AirportYWG
About the airport

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Frequently asked questions about the Chicago — Winnipeg flight

How long is the flight from Chicago to Winnipeg?

A nonstop Chicago — Winnipeg flight takes about 2 h 38 min — the distance between the cities is around 1,155 km.

How far is it from Chicago to Winnipeg?

The distance from Chicago to Winnipeg is about 1,155 km, which a nonstop flight covers in around 2 h 38 min.

Are there direct flights from Chicago to Winnipeg?

Yes, there are nonstop flights Chicago — Winnipeg — around 28 flights per week.

Which airlines fly from Chicago to Winnipeg?

Airlines operating Chicago — Winnipeg include United Airlines, Air Canada. See the full list with schedules in the "Airlines" section on this page.

Which airports do Chicago — Winnipeg flights use?

Flights from Chicago depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport, and arrive at Winnipeg James Armstrong Richardson International Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Chicago to Winnipeg?

The price of a Chicago — Winnipeg ticket depends on your travel date, season and demand: it is usually cheapest to fly in September, and most expensive in April. Tickets typically cost between $156 and $347. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Chicago — Winnipeg?

Flights Chicago — Winnipeg are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is September. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Chicago to Winnipeg?

To catch a low fare Chicago — Winnipeg, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually September.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.