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Cheap flight tickets from Winnipeg to Chicago

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Compare Winnipeg to Chicago flight deals

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Flight deals from Winnipeg to Chicago

Looking for a cheap last-minute deal or the best return flight from Winnipeg to Chicago? Find the lowest prices on one-way and return tickets right here.
Chicago.RM1,163 per passenger.Departing Mon, 28 Apr, returning Mon, 5 May.Return flight with WestJet and Frontier Airlines.Outbound indirect flight with WestJet, departs from Winnipeg on Mon, 28 Apr, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Mon, 5 May, arriving in Winnipeg.Price includes taxes and charges.From RM1,163, select.
Chicago.RM1,163 per passenger.Departing Tue, 3 Jun, returning Wed, 4 Jun.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Winnipeg on Tue, 3 Jun, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Wed, 4 Jun, arriving in Winnipeg.Price includes taxes and charges.From RM1,163, select.
Chicago.RM1,164 per passenger.Departing Wed, 20 Aug, returning Sat, 20 Sep.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Winnipeg on Wed, 20 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Sat, 20 Sep, arriving in Winnipeg.Price includes taxes and charges.From RM1,164, select.
Chicago.RM1,220 per passenger.Departing Wed, 10 Sep, returning Wed, 8 Oct.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Winnipeg on Wed, 10 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Wed, 8 Oct, arriving in Winnipeg.Price includes taxes and charges.From RM1,220, select.
Chicago.RM1,220 per passenger.Departing Wed, 13 Aug, returning Sat, 16 Aug.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Winnipeg on Wed, 13 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Sat, 16 Aug, arriving in Winnipeg.Price includes taxes and charges.From RM1,220, select.
Chicago.RM1,220 per passenger.Departing Wed, 16 Jul, returning Wed, 30 Jul.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Winnipeg on Wed, 16 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Wed, 30 Jul, arriving in Winnipeg.Price includes taxes and charges.From RM1,220, select.
Chicago.RM1,220 per passenger.Departing Wed, 10 Sep, returning Wed, 24 Sep.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Winnipeg on Wed, 10 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Wed, 24 Sep, arriving in Winnipeg.Price includes taxes and charges.From RM1,220, select.
Chicago.RM1,220 per passenger.Departing Wed, 16 Jul, returning Wed, 6 Aug.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Winnipeg on Wed, 16 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Wed, 6 Aug, arriving in Winnipeg.Price includes taxes and charges.From RM1,220, select.

Find the cheapest month to fly from Winnipeg to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Winnipeg to Chicago flights are currently cheapest in June.
Mar
from RM2,444
Apr
from RM1,647
May
from RM1,390
Jun
from RM1,163
Jul
from RM1,220
Aug
from RM1,220
Sep
from RM1,220
Oct
Find prices
Nov
from RM2,017
Dec
Find prices
Jan
Find prices
Feb
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Direct flights from Winnipeg to Chicago

Alternative Winnipeg to Chicago routes

Looking for the cheapest, fastest or easiest route from Winnipeg to Chicago? You could fly into the following airports instead.

Winnipeg to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRM1,163
Cheapest month to flyJune
Average flight time2 hrs, 29 mins
Most popular airlineUnited
Average flights per week59

Finding cheap flights from Winnipeg to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Winnipeg to Chicago is RM1,163. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 29 minutes is the average flight time from Winnipeg to Chicago.
United, SkyWest Airlines and Air New Zealand fly direct from Winnipeg to Chicago.
As of March 2025, there are 59 flights per week flying from Winnipeg to Chicago.
The cheapest month to fly from Winnipeg to Chicago is usually March 2025.
If you're flying from Winnipeg Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from RM1,163.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Winnipeg Airport to Chicago on Tuesday, 3 June 2025.
Yes – the average flight time is 2 hours and 29 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In March, the average temperature is usually around 3°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, WestJet and Air Canada offer the cheapest flight tickets to Chicago.

Flying from Winnipeg James Armstrong Richardson International Airport (YWG) to Chicago: what you need to know

  • Chicago and Winnipeg (where Winnipeg James Armstrong Richardson International Airport is located) share the UTC-5 timezone. That means you won't need to change your watch once you land.

  • The busiest route is from Winnipeg James Armstrong Richardson International Airport (YWG) to O'Hare International Airport (ORD). You can choose from 10 services every week between these two airports. If you want to take off as soon as possible, the earliest flight from YWG to ORD is the 14:15 United service. If you prefer to travel later, the last departure is at 14:25 with United.

  • To ensure you catch your flight from YWG to Chicago, allow plenty of time for things like baggage drop and finding your gate. Arriving two hours ahead of international departures and one hour before domestic flights is the general travel rule.

  • During popular months like July, it's a good idea to get to the airport well in advance. Arrive two hours before a domestic departure and four hours ahead of an international flight when you travel during a peak period in general.

  • You can catch a direct flight from Winnipeg James Armstrong Richardson International Airport to Chicago that touches down at O'Hare International Airport (ORD).

  • United is a popular airline that offers direct flights from Winnipeg James Armstrong Richardson International Airport to Chicago.

  • If you have a passport from Canada and want to travel to United States for tourism purposes, you won't need a visa. However, visa and entry requirements may vary based on the length and purpose of your stay and are subject to change. For the most up-to-date information, check with your destination's nearest embassy or consulate before reserving a cheap ticket from Winnipeg James Armstrong Richardson International Airport to Chicago.

  • Located around 8 kilometres from central Winnipeg, YWG can be reached in about 17 minutes by car (depending on traffic). The same journey by public transport takes roughly 55 minutes.

  • Catching an early flight from Winnipeg James Armstrong Richardson International Airport to Chicago? Avoid the hassle of rushing to the terminal (and enjoy a little extra shut-eye) by picking one of these hotels close to YWG:

How to find the cheapest flights from Winnipeg James Armstrong Richardson International Airport (YWG) to Chicago

  • The lowest price we've found for a one-way ticket from Winnipeg James Armstrong Richardson International Airport to Chicago is RM687. The cheapest price for a return flight is RM1,163. Remember fares may change due to demand at the time of booking.

  • Book 10 months before you want to travel. After crunching the numbers on our calendar, this is how far you'll want to book ahead to find cheap tickets from YWG to Chicago.

  • The cheapest month for tickets from Winnipeg James Armstrong Richardson International Airport to Chicago is June. Compare prices using the 'Whole month' tool to find the cheapest day to fly.

  • Set up a Price Alert for cheap tickets from YWG to Chicago. There's no need to search every day to see whether prices have dropped. We'll update you the moment the price changes.

  • Use the filters to tailor your flights from Winnipeg James Armstrong Richardson International Airport to Chicago. Pick your ideal departure and arrival times, number of stops and airlines. Or sort your results by 'Cheapest' to see the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

Chicago Midway International Airport (MDW)

Best time to go to Chicago

  • August is the busiest month for flights from Winnipeg James Armstrong Richardson International Airport to Chicago. To escape the crowds, head to Chicago in February when things are quieter.

  • Before booking a flight from Winnipeg James Armstrong Richardson International Airport to Chicago, think about the type of weather you enjoy. July is the warmest month in Chicago, with temperatures ranging from 15ºC to 29ºC.

  • If you like travelling in cooler conditions, look for a cheap flight from YWG to Chicago in January when temperatures average between -12ºC and 3ºC.

More about Chicago

  • When it comes to searching for somewhere to rest your head, you'll find the most popular stays in Chicago right here. Check out these hotels after you've booked your flight from Winnipeg James Armstrong Richardson International Airport to Chicago:

  • Millennium Park and Art Institute of Chicago are just a couple of the top-rated attractions to put on your Chicago must-do list. Keep the momentum going by heading to LandShark Beer Garden at Navy Pier.

Complete your Chicago trip with a car rental

  • We use the same magic that helped you find your cheap flight from Winnipeg James Armstrong Richardson International Airport to Chicago to track down deals on car rentals. Search for your ride in seconds and compare offers in one place. Plus we give you all the info you need on car rentals in Chicago, from the most popular car type to the average daily price.

Plan the rest of your trip from Winnipeg to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.