Cheap Flights from Winnipeg (YWG) to Chicago (CHIA)

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Flight deals from Winnipeg Airport to Chicago

Looking for a cheap last-minute deal or the best return flight from Winnipeg Airport to Chicago? If you want to travel next month, return fares start from £250. Find the lowest prices on one-way and return tickets right here.

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.

Direct flights from Winnipeg to Chicago

Winnipeg to Chicago: Flight information

The things to know before you go.
Cheapest flight found£121
Cheapest month to flyJune
Average flight time2 hrs, 31 mins
Most popular airlineUnited
Average flights per week54

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 £249. 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 31 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 April 2026, there are 54 flights per week flying from Winnipeg to Chicago.
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 15.8 miles away from the centre of Chicago. We've found flights into this airport from £249.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Winnipeg Airport to Chicago on Thursday, 17 September 2026.
Yes – the average flight time is 2 hours and 31 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 April, the average temperature is usually around 8°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 Intl Airport (YWG) to Chicago: what you need to know

  • Expect to be travelling for 2 hours 25 minutes. On average, that's the duration of a direct flight from Winnipeg James Armstrong Richardson Intl Airport to Chicago.

  • Winnipeg (the location of Winnipeg James Armstrong Richardson Intl Airport) and Chicago are in the same timezone — UTC-6.

  • The busiest route is from Winnipeg James Armstrong Richardson Intl Airport (YWG) to Chicago O'Hare International Airport (ORD). There are ten weekly services between these two airports. United Airlines offers a 07:00 departure between YWG and ORD.

  • To avoid rushing for your YWG to Chicago flight, leave plenty of time for things like check-in and baggage drop. Arriving two hours before international departures and an hour before domestic flights is the general rule.

  • During popular months like July, it's a good idea to get to the airport even earlier. Arrive two hours before a domestic departure and four hours ahead for international flights when you travel during high season in general.

  • Start your trip at YWG and travel nonstop to Chicago O'Hare International Airport (ORD). That's where you can expect to land when searching for Winnipeg James Armstrong Richardson Intl Airport to Chicago tickets.

  • Book your ticket with United Airlines. This airline offers direct flights from Winnipeg James Armstrong Richardson Intl Airport to Chicago.

  • YWG is around 6 kms (4 miles) from central Winnipeg. If you're catching a taxi, ride-sharing or driving from the centre, it'll take 20 minutes or so to get there, depending on the traffic. If you're taking public transport, expect the trip time to be around 40 minutes.

  • Searching for a hotel close to YWG? If you're catching an early flight from Winnipeg James Armstrong Richardson Intl Airport to Chicago, these stays put the terminal practically at your doorstep:

  • When it comes to the on-time performance of Winnipeg James Armstrong Richardson Intl Airport, data shows 73% of flights arrive within the expected time frame.

  • The address for YWG is 2000 Wellington Avenue.

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

  • The best price we've seen for a one-way Winnipeg James Armstrong Richardson Intl Airport to Chicago flight is £121. The cheapest price for a return flight is £249. Remember fares can change due to demand at the time of booking.

  • Book one month before you want to fly. Pricing trends suggest that this is the ideal window for finding cheap flights from YWG to Chicago.

  • June is the best month for landing an awesome deal on Winnipeg James Armstrong Richardson Intl Airport to Chicago tickets. If you'd like to travel at a different time of year, the 'Whole month' tool will show you the lowest prices for each month.

  • Cut down on the time spent looking for cheap flights from YWG to Chicago by creating a Price Alert. We'll send you an email or push notification on the app when a lower fare pops up.

  • Select your ideal arrival and departure times, number of stops and airlines with our filters. Then, sort the results for your flight from Winnipeg James Armstrong Richardson Intl Airport to Chicago by 'Best,' 'Cheapest' or 'Fastest.'

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Chicago O'Hare International Airport (ORD) to the centre of Chicago takes about 30 minutes to reach by car. The centre is roughly 27 kms (17 miles) away.

  • Getting to the centre by public transport takes about 45 minutes.

  • If you're arriving on a late flight from Winnipeg James Armstrong Richardson Intl Airport to Chicago, few things beat the convenience of staying near the terminal. Collect your bags from the carousel and then be showered and sleeping soon after at one of these hotels near ORD:

  • Get the best deal by booking your ride from Chicago O'Hare International Airport about four weeks ahead of your flight from YWG to Chicago.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • After your flight from Winnipeg James Armstrong Richardson Intl Airport to Chicago has hit the tarmac, you can make your way to the city centre in about 25 minutes by car. Central Chicago is roughly 16 kms (10 miles) from Chicago Midway International Airport (MDW).

  • Travelling by public transport will take about 30 minutes.

  • There are some great places to call home for the night near MDW. Unwind and get cosy after your YWG to Chicago flight at one of these perfectly located options:

  • Secure your first choice, not your last resort. Booking your ride from MDW four weeks in advance often means lower prices and a wider choice of vehicles.

  • Chicago Midway International Airport is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Hop off your flight from Winnipeg James Armstrong Richardson Intl Airport to Chicago and head for your hotel or start exploring right away. Central Chicago is around 145 kms (90 miles) from Chicago Rockford International Airport (RFD) and usually takes 1 hour 40 minutes to reach by car.

  • If you go by public transport, the journey time is about 2 hours.

  • Enjoy a restful, unhurried start to your break by checking in to a hotel near RFD after your YWG to Chicago flight. Recover from a day of travel or simply take a moment to find your footing in a new place at:

  • If you're looking for a certain kind of vehicle, booking early gives you a better shot at snagging what you want. Book your ride from RFD a few weeks ahead of your flight from Winnipeg James Armstrong Richardson Intl Airport to Chicago.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

Best time to go to Chicago

  • It's time to choose your dates for your flight from Winnipeg James Armstrong Richardson Intl Airport to Chicago. July is the busiest month to travel to Chicago. If you want a quieter atmosphere, go in January.

  • The warmest month in Chicago is July, with temperatures ranging between 16ºC and 28ºC. Book your Winnipeg James Armstrong Richardson Intl Airport to Chicago plane ticket then if this is the type of weather you enjoy.

  • Search for cheap tickets from YWG to Chicago in January if you'd rather travel when it's cooler. Temperatures are at their lowest then, ranging between -12ºC and 3ºC on average.

More about Chicago

  • When it comes to looking for somewhere to rest your head, you'll find the best places to stay in Chicago right here. Check out these hotels after you've booked your flight from Winnipeg James Armstrong Richardson Intl Airport to Chicago:

  • There are so many things to discover in this city it can be tricky to know where to begin. Art Institute of Chicago, Millennium Park and Willis Tower are highlights which should feature on any well-planned Chicago itinerary.

Explore more of the United States

  • Columbus is just one of the many places in the United States waiting to be explored once you've taken in the sights of Chicago. Around 451 kms (280 miles) away to the southeast, check out popular attractions including Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • Indianapolis is another must-experience destination in the United States and is around 257 kms (160 miles) southeast of Chicago. No trip is complete without experiencing Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

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