C$528 Cheap Flights from Chicago (CHIA) to Winnipeg (YWG)

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Flight deals from Chicago to Winnipeg

Looking for a cheap last-minute deal or the best return flight from Chicago to Winnipeg Airport? If you want to travel next month, return fares start from C$607. Find the lowest prices on one-way and return tickets right here.

Winnipeg.C$228 per passenger.Departing Fri., Sep. 25.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Chicago O'Hare International on Fri., Sep. 25, arriving in Winnipeg.Price includes taxes and charges.From C$228, select.

Winnipeg.C$249 per passenger.Departing Sat., Jun. 27.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Chicago Midway on Sat., Jun. 27, arriving in Winnipeg.Price includes taxes and charges.From C$249, select.

Winnipeg.C$254 per passenger.Departing Tue., Jul. 7.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Chicago Midway on Tue., Jul. 7, arriving in Winnipeg.Price includes taxes and charges.From C$254, select.

Winnipeg.C$255 per passenger.Departing Thu., Oct. 22.One-way flight with WestJet.Outbound indirect flight with WestJet, departs from Chicago O'Hare International on Thu., Oct. 22, arriving in Winnipeg.Price includes taxes and charges.From C$255, select.

Winnipeg.C$284 per passenger.Departing Tue., Aug. 11.One-way flight with WestJet.Outbound indirect flight with WestJet, departs from Chicago O'Hare International on Tue., Aug. 11, arriving in Winnipeg.Price includes taxes and charges.From C$284, select.

Winnipeg.C$295 per passenger.Departing Fri., Nov. 6.One-way flight with WestJet.Outbound indirect flight with WestJet, departs from Chicago O'Hare International on Fri., Nov. 6, arriving in Winnipeg.Price includes taxes and charges.From C$295, select.

Winnipeg.C$428 per passenger.Departing Sun., Jan. 17.One-way flight with American Airlines.Outbound indirect flight with American Airlines, departs from Chicago O'Hare International on Sun., Jan. 17, arriving in Winnipeg.Price includes taxes and charges.From C$428, select.

Winnipeg.C$455 per passenger.Departing Mon., Dec. 28.One-way flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Mon., Dec. 28, arriving in Winnipeg.Price includes taxes and charges.From C$455, select.

Winnipeg.C$464 per passenger.Departing Mon., Aug. 3.One-way flight with Air Canada.Outbound direct flight with Air Canada departs from Chicago O'Hare International on Mon., Aug. 3, arriving in Winnipeg.Price includes taxes and charges.From C$464, select.

Winnipeg.C$484 per passenger.Departing Thu., Oct. 22.One-way flight with Air Canada.Outbound direct flight with Air Canada departs from Chicago O'Hare International on Thu., Oct. 22, arriving in Winnipeg.Price includes taxes and charges.From C$484, select.

Winnipeg.C$485 per passenger.Departing Mon., Dec. 28.One-way flight with Air Canada.Outbound direct flight with Air Canada departs from Chicago O'Hare International on Mon., Dec. 28, arriving in Winnipeg.Price includes taxes and charges.From C$485, select.

Winnipeg.C$485 per passenger.Departing Sun., Jan. 17.One-way flight with Air Canada.Outbound direct flight with Air Canada departs from Chicago O'Hare International on Sun., Jan. 17, arriving in Winnipeg.Price includes taxes and charges.From C$485, select.

Winnipeg.C$489 per passenger.Departing Tue., Jul. 7.One-way flight with Air Canada.Outbound direct flight with Air Canada departs from Chicago O'Hare International on Tue., Jul. 7, arriving in Winnipeg.Price includes taxes and charges.From C$489, select.

Winnipeg.C$493 per passenger.Departing Sat., Nov. 14.One-way flight with Air Canada.Outbound direct flight with Air Canada departs from Chicago O'Hare International on Sat., Nov. 14, arriving in Winnipeg.Price includes taxes and charges.From C$493, select.

Winnipeg.C$493 per passenger.Departing Sun., Sep. 20.One-way flight with Air Canada.Outbound direct flight with Air Canada departs from Chicago O'Hare International on Sun., Sep. 20, arriving in Winnipeg.Price includes taxes and charges.From C$493, select.

Winnipeg.C$506 per passenger.Departing Sat., Jun. 27.One-way flight with Air Canada.Outbound direct flight with Air Canada departs from Chicago O'Hare International on Sat., Jun. 27, arriving in Winnipeg.Price includes taxes and charges.From C$506, select.

Find the cheapest month to fly from Chicago to Winnipeg

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Winnipeg flights are currently cheapest in September.

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Which airlines fly from Chicago to Winnipeg?

Chicago to Winnipeg: Alternative routes

Compare routes from Chicago to Winnipeg below. You may find an airport to fly into that's cheaper, faster, or easier than Winnipeg.

Winnipeg

7km from central Winnipeg

ClosestCheapest

from C$228

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Chicago to Winnipeg: Flight information

The things to know before you go.

Cheapest flight found	C$228
Cheapest month to fly	September
Average flight time	2 hrs, 37 mins
Most popular airline	United
Average flights per week	45

Finding cheap flights from Chicago to Winnipeg: Frequently asked questions

How much are return flights from Chicago to Winnipeg?

The best price we found for a return flight from Chicago to Winnipeg is C$528. 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.

How long does it take to fly from Chicago to Winnipeg?

2 hours and 37 minutes is the average flight time from Chicago to Winnipeg.

Which airlines fly direct from Chicago to Winnipeg?

United, SkyWest Airlines and Air New Zealand fly direct from Chicago to Winnipeg.

How many flights are there a week from Chicago to Winnipeg?

As of June 2026, there are 46 flights per week flying from Chicago to Winnipeg.

When is the cheapest time to fly from Chicago to Winnipeg?

The cheapest month to fly from Chicago to Winnipeg is usually September.

Which upcoming date is cheapest to fly from Chicago to Winnipeg Airport on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Winnipeg Airport on Saturday, September 19, 2026.

Can I get a direct flight from Chicago to Winnipeg Airport?

Yes – the average flight time is 2 hours and 37 minutes.

How can I find the best flight deal to Winnipeg?

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 Winnipeg 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.

When is the best time to book flights to Winnipeg?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Winnipeg is around 40 days in advance, so don’t leave your flight to the last minute.

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

Start your vacation planning by considering where you'll catch your flight from Chicago to Winnipeg James Armstrong Richardson International Airport (YWG). O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are the main airports in Chicago.
Winnipeg (where Winnipeg James Armstrong Richardson International Airport is located) and Chicago share the UTC-5 timezone. Same timezone means no confusion when scheduling your trip.
Arrive at the airport on time so you don't miss your flight from Chicago to YWG. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid the stress of rushing.
With more travellers during busy months like August, get to the terminal earlier than usual. Two hours for domestic flights and up to four for international journeys will allow for extra wait times. Remember things also get busy during major holidays like July Fourth.

Airports in Chicago

O'Hare International Airport (ORD)

Think about adding a stopover to potentially save on your flight from Chicago to YWG. Just uncheck 'Direct flights only' when browsing departures from O'Hare International Airport (ORD). Take a break (and maybe save some cash) by stopping at one of these popular options:
- Pearson International Airport (YYZ)
- Nashville International Airport (BNA)
- Minneapolis-St. Paul International Airport (MSP)
The distance from central Chicago to ORD is about 40 kilometres. Use Google Maps for the quickest route, whether you prefer to drive or use public transport.
In search of a handy hotel near O'Hare International Airport? If you've booked an early flight from Chicago to Winnipeg James Armstrong Richardson International Airport, these accommodation options will have you moments from your departure lounge:

Chicago Midway International Airport (MDW)

Chicago Midway International Airport (MDW) operates direct flights from Chicago to Winnipeg James Armstrong Richardson International Airport (YWG).
From MDW, direct flights from Chicago to YWG can be booked with United.
MDW is about 19 kilometres from central Chicago. It'll take you 21 minutes or so to get to the airport if you're driving from the city centre. Public transport takes approximately 46 minutes.
You're off on vacation, so why not book an extra night away from home? Consider checking in to one of these accommodation options near Chicago Midway International Airport the day before your flight from Chicago to YWG:

About Winnipeg James Armstrong Richardson International Airport (YWG)

If you're arriving on a late flight from Chicago to Winnipeg James Armstrong Richardson International Airport, nothing beats the convenience of staying close to the terminal. Collect your bags from the carousel and then be showered and relaxing not long after at one of these options near YWG:

Getting from Winnipeg James Armstrong Richardson International Airport (YWG) to central Winnipeg

Winnipeg James Armstrong Richardson International Airport to central Winnipeg takes about 17 minutes in a car. It's approximately 8 kilometres away. Find out what options are available, such as cabs, car rentals or ride-sharing services.
It takes roughly 55 minutes to get there by public transport.

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

C$228 is the lowest price we've seen for a one-way ticket from Chicago to Winnipeg James Armstrong Richardson International Airport. Return flights start from C$528. Fares are subject to availability and may change at any time.
It's usually smart to book as early as possible if you're hoping to get flight tickets from Chicago to YWG. That's because airlines change prices based on demand, which tends to rise closer to the date of departure.
The 'Whole month' search tool shows you the cheapest tickets from Chicago to Winnipeg James Armstrong Richardson International Airport across the entire month. It's a great way to find a bargain if your travel dates are flexible.
Snapping up a cheap ticket from Chicago to YWG couldn't be easier with Price Alerts. All you need to do is set up one of these automatic alerts and we'll get in touch as soon as the price has fallen.
Customize your journey by applying filters. Adjust the number of stops, total duration, and departure and arrival times to find the right flight from Chicago to Winnipeg James Armstrong Richardson International Airport. You can also sort the results to see the 'Fastest,' 'Cheapest' or 'Best' options first.

The best time to fly from Chicago to Winnipeg James Armstrong Richardson International Airport (YWG)

It's time to figure out your trip dates for your flight from Chicago to Winnipeg James Armstrong Richardson International Airport. July is the most popular month for a trip to Winnipeg. If you want a quieter atmosphere, go in May.
Before you book a flight from Chicago to YWG, think about the type of weather you enjoy. July is the warmest month in Winnipeg, with temperatures ranging from 12ºC to 29ºC.
If you'd rather travel in cooler conditions, search for a cheap flight from Chicago to Winnipeg James Armstrong Richardson International Airport in January when temperatures average between -25ºC and -6ºC.

More about Winnipeg

Start your Winnipeg trip off on the right foot by choosing the perfect place to stay. After booking your flight from Chicago to Winnipeg James Armstrong Richardson International Airport, check out our range of hotels including:
Every great adventure has to include a little sightseeing. The Forks Market, The Forks National Historic Site and Canadian Museum for Human Rights are must-do's during your Winnipeg adventure.

Complete your Winnipeg trip with a car rental

Once you've booked your hotel and cheap flight from Chicago to Winnipeg James Armstrong Richardson International Airport, the next task is choosing one of our car rentals in Winnipeg. Explore the deals and easily compare your options on price, fuel policies, and more.