Cheap flights from Winnipeg to Chicago

James Armstrong Richardson
YWG
Chicago FSS
CHI

Flight deals from Winnipeg to Chicago

Below you can see the best deals on flights Winnipeg — Chicago 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 27 September, from $140.

Top 10 cheap flights from Winnipeg to Chicago

WS
WS
$ 177

Winnipeg — Chicago

07:00—16:40
6 Sep 2026
9 h 40 m
1 stop
WS
WS
$ 177

Winnipeg — Chicago

07:00—16:40
10 Sep 2026
9 h 40 m
1 stop
WS
WS
$ 177

Winnipeg — Chicago

07:00—16:40
5 Sep 2026
9 h 40 m
1 stop
WS
WS
$ 177

Winnipeg — Chicago

07:00—16:40
11 Sep 2026
9 h 40 m
1 stop
WS
DL
DL
$ 178

Winnipeg — Chicago

07:45—20:30
9 Sep 2026
12 h 45 m
2 stops
WS
DL
DL
$ 178

Winnipeg — Chicago

06:15—20:30
9 Sep 2026
14 h 15 m
2 stops
WS
DL
DL
$ 178

Winnipeg — Chicago

06:15—19:15
9 Sep 2026
13 h
2 stops
WS
DL
DL
$ 178

Winnipeg — Chicago

07:45—22:18
9 Sep 2026
14 h 33 m
2 stops
WS
DL
DL
$ 178

Winnipeg — Chicago

19:55—09:07
11 Sep 2026
13 h 12 m
2 stops
WS
DL
DL
$ 178

Winnipeg — Chicago

19:55—10:37
11 Sep 2026
14 h 42 m
2 stops

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Winnipeg — Chicago flight

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

The route has direct flights — around 29 flights per week, flights are operated by United Airlines, Air Canada, a nonstop flight takes about 2 h 34 min, the distance between the cities is around 1,155 km.

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

Facts about this route

from $140Min. price
SeptemberCheapest
JunePeak season
YesDirect flights
1,155 kmDistance
2 h 34 minTravel time
2Airlines
29 / wkFlights

Flight schedule from Winnipeg to Chicago

The table shows direct flights from Winnipeg to Chicago on the selected date. The flight takes approximately 2 h 34 min. Regular flights are operated by United Airlines and Air Canada. Departures from Winnipeg James Armstrong Richardson International Airport airports, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway 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: 16 Aug 2026

Flight ticket prices by day: Winnipeg — Chicago

Below is a calendar of the lowest flight ticket prices for Winnipeg — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $140 in September, and the most expensive are around $331 in June. 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.

 
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Prices by month

Average one-way fares from Winnipeg to Chicago by month. Tickets are usually cheapest in February (around $226) and priciest in August (about $346) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$238lowMay$286mediumSep$232low
Feb$226lowJun$250lowOct$226low
Mar$262mediumJul$334highNov$328high
Apr$322highAug$346highDec$340high

Some values are estimated based on seasonality.

When to fly

Weather in Chicago: it is warmest in July (up to 27 °C on average) and coolest in January (around 0 °C). The driest month is November.

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

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

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

  • Book ahead: fares for Winnipeg — Chicago 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.
  • The cheapest month to fly to Chicago 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.

Airlines

Flights on the Winnipeg — Chicago route are operated by 2 airlines; United Airlines runs the most flights (around 93% of all flights). Compare carriers, flight shares and schedules below.

  • United AirlinesUA
    9x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight YWG → ORD9x/week
      Duration
      2h 32m
      Days
      MTWTFSS
    93.1%Open →
  • Air CanadaAC
    1x/week
    WebsiteFleet: 20346M pax/year
    • Direct flight YWG → ORD1x/week
      Duration
      2h 21m
      Days
      MTWTFSS
    6.9%Open →

Cities and airports on the Winnipeg — Chicago route

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

Departure

Winnipeg

YWG
Canada
About the cityHow to get thereWeatherAll about the country Canada
Arrival

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

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Frequently asked questions about the Winnipeg — Chicago flight

How long is the flight from Winnipeg to Chicago?

A nonstop Winnipeg — Chicago flight takes about 2 h 34 min — the distance between the cities is around 1,155 km.

How far is it from Winnipeg to Chicago?

The distance from Winnipeg to Chicago is about 1,155 km, which a nonstop flight covers in around 2 h 34 min.

Are there direct flights from Winnipeg to Chicago?

Yes, there are nonstop flights Winnipeg — Chicago — around 29 flights per week.

Which airlines fly from Winnipeg to Chicago?

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

Which airports do Winnipeg — Chicago flights use?

Flights from Winnipeg depart from Winnipeg James Armstrong Richardson International Airport, and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway 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 Winnipeg to Chicago?

The price of a Winnipeg — Chicago ticket depends on your travel date, season and demand: it is usually cheapest to fly in September, and most expensive in June. Tickets typically cost between $140 and $331. Check the current lowest fare and low-price calendar on this page.

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

Flights Winnipeg — Chicago 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 Winnipeg to Chicago?

To catch a low fare Winnipeg — Chicago, 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.

Where else you can fly from Winnipeg

See all
TorontoVancouverCalgaryMinneapolisEdmontonMontrealThunder BayOttawaSaskatoonHalifaxPuerto VallartaDenverPhoenixReginaKelownaCancunLas VegasVictoriaPalm SpringsLondonNashvilleAtlantaHuatulcoFort LauderdaleMontego BaySan Jose del CaboOrlandoRankin InletLiberiaReykjavikSt. John'sManhattanBismarckLincolnHartfordAppleton

Where else you can fly from Chicago

See all
New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverNashvilleLondonIndianapolisSan DiegoMontrealMilwaukeeSt. LouisCharlottePhiladelphiaColumbusKansas CityPhoenixMiamiLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochester

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