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Cheap flights from Winnipeg to Chicago

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Flight deals from Winnipeg to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Winnipeg to Chicago? Find the lowest prices on one-way and round-trip tickets right here.
Chicago.C$270 per passenger.Departing Wed, Sep 24, returning Sat, Sep 27.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Winnipeg on Wed, Sep 24, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departing from Chicago O'Hare International on Sat, Sep 27, arriving in Winnipeg.Price includes taxes and charges.From C$270, select.
Chicago.C$317 per passenger.Departing Tue, Aug 26, returning Sat, Sep 13.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Winnipeg on Tue, Aug 26, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departing from Chicago O'Hare International on Sat, Sep 13, arriving in Winnipeg.Price includes taxes and charges.From C$317, select.
Chicago.C$317 per passenger.Departing Sat, Oct 4, returning Sat, Oct 11.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Winnipeg on Sat, Oct 4, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departing from Chicago O'Hare International on Sat, Oct 11, arriving in Winnipeg.Price includes taxes and charges.From C$317, select.
Chicago.C$460 per passenger.Departing Tue, Sep 16, returning Tue, Sep 23.Round-trip flight with United.Outbound direct flight with United departing from Winnipeg on Tue, Sep 16, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Tue, Sep 23, arriving in Winnipeg.Price includes taxes and charges.From C$460, select.
Chicago.C$460 per passenger.Departing Fri, Oct 17, returning Mon, Oct 20.Round-trip flight with United.Outbound direct flight with United departing from Winnipeg on Fri, Oct 17, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Mon, Oct 20, arriving in Winnipeg.Price includes taxes and charges.From C$460, select.
Chicago.C$483 per passenger.Departing Fri, Nov 7, returning Mon, Nov 10.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Winnipeg on Fri, Nov 7, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departing from Chicago O'Hare International on Mon, Nov 10, arriving in Winnipeg.Price includes taxes and charges.From C$483, select.
Chicago.C$487 per passenger.Departing Mon, Aug 18, returning Wed, Aug 27.Round-trip flight with WestJet and Spirit Airlines.Outbound indirect flight with WestJet, departing from Winnipeg on Mon, Aug 18, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departing from Chicago O'Hare International on Wed, Aug 27, arriving in Winnipeg.Price includes taxes and charges.From C$487, select.
Chicago.C$505 per passenger.Departing Fri, Aug 22, returning Mon, Aug 25.Round-trip flight with United.Outbound direct flight with United departing from Winnipeg on Fri, Aug 22, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Mon, Aug 25, arriving in Winnipeg.Price includes taxes and charges.From C$505, 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 September.
Aug
from C$487
Sep
from C$270
Oct
from C$317
Nov
from C$483
Dec
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Jan
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Feb
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Mar
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Apr
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May
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Jun
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Jul
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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 foundC$270
Cheapest month to flySeptember
Average flight time2 hrs, 29 mins
Most popular airlineUnited
Average flights per week37

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 round-trip flight from Winnipeg to Chicago is C$270. 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.
There are 72 flights per week flying from Winnipeg to Chicago, as of August 2025.
The cheapest month to fly from Winnipeg to Chicago is usually September.
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 center of Chicago. We've found flights to this airport from C$270.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Winnipeg Airport to Chicago on Wednesday, September 24, 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 August, the average temperature is usually around 22°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 United offer the cheapest flight tickets to Chicago.

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

  • Approximately 2 hours 30 minutes is how long you'll be travelling on a direct flight from Winnipeg James Armstrong Richardson International Airport to Chicago.

  • Chicago's timezone is UTC-5, which is the same as Winnipeg (the location of Winnipeg James Armstrong Richardson International Airport).

  • With ten flights a week between the two airports, Winnipeg James Armstrong Richardson International Airport (YWG) to O'Hare International Airport (ORD) is the most popular route. Hop on United Airlines's 07:00 flight to get your journey from YWG to ORD underway.

  • To avoid missing your YWG to Chicago flight, allow plenty of time to navigate the airport and find your gate. Arriving two hours ahead of international departures and one hour before domestic flights is the general travel rule.

  • Longer lines at security and check-in are more likely if you're heading away during high season, so give yourself a bit more breathing room. A good rule of thumb for peak periods? Arrive up to four hours early for international flights and two hours for domestic departures.

  • You can book a direct Winnipeg James Armstrong Richardson International Airport to Chicago ticket. Begin your journey at YWG and end it at O'Hare International Airport (ORD).

  • United Airlines is a popular carrier that operates direct flights from Winnipeg James Armstrong Richardson International Airport to Chicago.

  • YWG is around 6 kilometres from central Winnipeg. If you're ride-sharing, catching a cab or driving from the centre, it'll take you 15 minutes or so to get there, depending on the traffic. If you're using public transport, expect the trip time to be around 55 minutes.

  • Want a stress-free start to your vacation? Stay near YWG. Whether you're taking an early flight from Winnipeg James Armstrong Richardson International Airport to Chicago or want to avoid feeling rushed, these hotels are all about convenience:

  • 61.28% of flights leaving from Winnipeg James Armstrong Richardson International Airport arrive at their destination on schedule.

  • YWG's address is 2000 Wellington Avenue.

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

  • The best price we've found for a one-way Winnipeg James Armstrong Richardson International Airport to Chicago flight is C$162. The cheapest price for a return flight is C$270. Bear in mind fares can change due to availability at the time of booking.

  • Lock in cheap flights from YWG to Chicago by booking two months ahead. According to our research, that's the sweet spot for picking up a bargain.

  • Organize your trip for June. That's the best month for landing an incredible deal on Winnipeg James Armstrong Richardson International Airport to Chicago tickets. If you're flexible with your travel dates, use the 'Whole month' tool to access the lowest price across every month.

  • Spend less time searching for cheap flights from YWG to Chicago by creating a Price Alert. We'll send you an email or notification through the app when fares go down.

  • Save money on your flight from Winnipeg James Armstrong Richardson International Airport to Chicago with the help of our filters. Select your preferred times, airlines and number of stops, then sort the results by 'Cheapest' to see the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is roughly 40 kilometres. It takes about 35 minutes to reach the centre driving.

  • It'll take around 55 minutes if you're using public transport.

  • If you're coming in on a late flight from Winnipeg James Armstrong Richardson International Airport to Chicago, nothing beats the convenience of staying near the terminal. Grab your bags from the carousel and then be showered and sleeping soon after at one of these accommodation options near ORD:

  • Begin your adventure by picking up an O'Hare International Airport rental car. Grab your wheels from Routes Car Rentals, Dollar or Budget to explore Chicago and beyond.

  • Lock in the best deal by reserving your vehicle from O'Hare International Airport around four weeks before your flight from YWG to Chicago.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) is about 19 kilometres from the centre of Chicago. Following your flight from Winnipeg James Armstrong Richardson International Airport to Chicago, it'll take you around 20 minutes to reach the heart of the city in a ride-share or cab.

  • Travelling by public transport will take about 45 minutes.

  • You'll find some comfortable places ready to welcome you near MDW. Settle in and get cozy after your YWG to Chicago flight at any of these perfectly located options:

  • Forget about public transport schedules or slow-moving cab lines. Pick up a Chicago Midway International Airport rental car and let the journey unfold your way. Check out the availability and rates from Dollar, Hertz and Budget.

  • Don't pay more than you need to. Reserving your ride four weeks ahead of your arrival at MDW will save you money.

  • You'll find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Find your way to the city centre after your flight from Winnipeg James Armstrong Richardson International Airport to Chicago has arrived. Central Chicago is about 137 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 25 minutes to reach by car.

  • The journey will take about 4 hours 15 minutes on public transport.

  • Enjoy a more relaxed start to your break by staying at a hotel near RFD after your YWG to Chicago flight. Take a load off after a long travel day or simply give yourself time to find your footing in a new place at:

  • Whether you're searching for a budget-friendly compact for a solo getaway or a roomy SUV to fit the family, you'll find the right Chicago Rockford International Airport rental car for your needs. Browse the range of wheels available from suppliers such as Budget, Alamo and National.

  • Booking at least a few weeks in advance of your flight from Winnipeg James Armstrong Richardson International Airport to Chicago is always smart. As well as better deals, you'll be able to choose the vehicle make and model you prefer at RFD.

  • Chicago Rockford International Airport can be found at 2 Airport Cir.

Best time to go to Chicago

  • Before securing your flights from Winnipeg James Armstrong Richardson International Airport to Chicago, consider which time of year is best for you. Peak season in Chicago offers a lively atmosphere and plenty to do, while the off-season means you'll get cheaper deals on hotels and fewer crowds.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC (59ºF) and 29ºC (84ºF). Lock in your Winnipeg James Armstrong Richardson International Airport to Chicago flight ticket then if you enjoy this type of weather.

  • For cooler conditions, search for a cheap ticket from YWG to Chicago in January when temperatures average between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

  • Start your Chicago trip right by choosing the perfect place to stay. As soon as you've booked your flight from Winnipeg James Armstrong Richardson International Airport to Chicago, check out our selection of accommodation options including:

  • Art Institute of Chicago and Millennium Park are just two of the top-rated attractions to add to your Chicago to-do list. Keep the adventure rolling by checking out LandShark Beer Garden at Navy Pier.

Explore more of United States

  • Columbus is just one of the many cities in United States waiting to be explored once you've taken in the sights of Chicago. Around 451 kilometres away to the south-east, top sights here include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another well-known destination in United States and is around 257 kilometres south-east of Chicago. No journey is complete without dropping by The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

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.