Cheap Flights from Winnipeg to Chicago

Popular airlines from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago

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Find the cheapest month to fly from Winnipeg (YWG) to Chicago (CHI)

September is typically the cheapest month to fly

From S$358 - S$768 per traveller.

Graph displaying average flight prices per month

Winnipeg to Chicago route information
Origin airport
Winnipeg James Armstrong Richardson Intl.
Destination airport
CHI-All Airports
Distance
1086 km

Perfect flights from Winnipeg to Chicago

Your Journey from Winnipeg to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from Winnipeg to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including . Our selection of flights from Winnipeg James Armstrong Richardson Intl. to CHI-All Airports caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from airlines, you're bound to find the perfect flight.
 

Maximizing Value with Winnipeg to Chicago Flights

Experience the joy of finding cheap flights from Winnipeg James Armstrong Richardson Intl. to CHI-All Airports that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares and roundtrip prices *.
 

Pre-Flight Essentials

Ensure a smooth journey from Winnipeg to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Chicago

Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Winnipeg to Chicago Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Winnipeg to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Winnipeg to Chicago with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Winnipeg to Chicago with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from YWG to Chicago, IL (CHI-All Airports)?
Within the past 7 days on Expedia, for flights departing within the next year, the lowest price advertised for a round-trip journey from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago, IL (CHI-All Airports) was . Fares this good don't wait forever, so make sure you book yours ASAP. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from YWG to Chicago, IL (CHI-All Airports)?
We get that life can throw the odd curveball, so we've made it as simple as possible for you to cancel your trip online. Just head to the Customer Service Portal and follow the instructions.
How do I find cheap flights from Winnipeg Airport to Chicago, IL (CHI-All Airports) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for YWG to Chicago, IL (CHI-All Airports) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Winnipeg Airport to Chicago, IL (CHI-All Airports)?
With a flight distance of 1,100 kilometres, it's just a short hop from YWG to Chicago, IL (CHI-All Airports). It might be a quick flight, but it's still worth packing a book to read.
Which airlines fly direct from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago, IL (CHI-All Airports)?
You won't find any airlines flying directly between Winnipeg James Armstrong Richardson Intl. Airport (YWG) and Chicago, IL (CHI-All Airports), so be prepared to make at least one stop on your journey. A layover can be a good way to break up a trip!
Are Winnipeg Airport to Chicago, IL (CHI-All Airports) flight tickets cheaper when they're purchased at the last minute?
Booking last minute from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago, IL (CHI-All Airports) can be hit-or-miss. You may be able to find a bargain, but you could also completely miss out! If you'd prefer to start your trip planning ahead of time, Expedia compares flight deals up to 12 months in advance. Just keep in mind that not all airlines publish their prices that far in advance. Our suggestion? Check back often as updates are made frequently.

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