S$161 Cheap Flights from Kitchener to Chicago

View S$161 flight on Sat, 4 Oct, 2025Opens in a new window

Popular airlines from Kitchener, ON (YKF-Region of Waterloo Intl.) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Kitchener to Chicago (YKF-ORD)

Prices were available within the past 7 days and start at S$161 for one-way flights and S$258 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Thu, 2 Oct - Sun, 5 Oct
YKF
Kitchener
ORD
Chicago
S$258 Return, found 6 days ago
S$258
Return
found 6 days ago
Select Air Canada flight, departing Thu, 2 Oct from Kitchener to Chicago, returning Sun, 5 Oct, priced at S$258 found 6 days ago
Air Canada
Thu, 2 Oct - Sun, 5 Oct
YKF
Kitchener
ORD
Chicago
S$345 Return, found 6 days ago
S$345
Return
found 6 days ago
Select Air Canada flight, departing Thu, 2 Oct from Kitchener to Chicago, returning Sun, 5 Oct, priced at S$345 found 6 days ago
Air Canada
Fri, 26 Sep - Sun, 28 Sep
YKF
Kitchener
ORD
Chicago
S$349 Return, found 3 days ago
S$349
Return
found 3 days ago
Select Air Canada flight, departing Fri, 26 Sep from Kitchener to Chicago, returning Sun, 28 Sep, priced at S$349 found 3 days ago
Air Canada
Thu, 2 Oct - Sun, 5 Oct
YKF
Kitchener
ORD
Chicago
S$379 Return, found 6 days ago
S$379
Return
found 6 days ago
Select Air Canada flight, departing Thu, 2 Oct from Kitchener to Chicago, returning Sun, 5 Oct, priced at S$379 found 6 days ago
Air Canada
Thu, 11 Sep - Sun, 14 Sep
YKF
Kitchener
ORD
Chicago
S$384 Return, found 6 days ago
S$384
Return
found 6 days ago
Select Air Canada flight, departing Thu, 11 Sep from Kitchener to Chicago, returning Sun, 14 Sep, priced at S$384 found 6 days ago
Air Canada
Fri, 26 Sep - Sun, 28 Sep
YKF
Kitchener
ORD
Chicago
S$414 Return, found 3 days ago
S$414
Return
found 3 days ago
Select Air Canada flight, departing Fri, 26 Sep from Kitchener to Chicago, returning Sun, 28 Sep, priced at S$414 found 3 days ago
Air Canada
Thu, 11 Sep - Sun, 14 Sep
YKF
Kitchener
ORD
Chicago
S$418 Return, found 6 days ago
S$418
Return
found 6 days ago
Select Air Canada flight, departing Thu, 11 Sep from Kitchener to Chicago, returning Sun, 14 Sep, priced at S$418 found 6 days ago
Air Canada
Fri, 26 Sep - Sun, 28 Sep
YKF
Kitchener
ORD
Chicago
S$425 Return, found 3 days ago
S$425
Return
found 3 days ago
Select Air Canada flight, departing Fri, 26 Sep from Kitchener to Chicago, returning Sun, 28 Sep, priced at S$425 found 3 days ago
Air Canada
Tue, 17 Feb - Thu, 19 Feb
YKF
Kitchener
ORD
Chicago
S$443 Return, found 4 days ago
S$443
Return
found 4 days ago
Select Air Canada flight, departing Tue, 17 Feb from Kitchener to Chicago, returning Thu, 19 Feb, priced at S$443 found 4 days ago
Air Canada
Thu, 11 Sep - Sun, 14 Sep
YKF
Kitchener
ORD
Chicago
S$450 Return, found 6 days ago
S$450
Return
found 6 days ago
Select Air Canada flight, departing Thu, 11 Sep from Kitchener to Chicago, returning Sun, 14 Sep, priced at S$450 found 6 days ago
Kitchener to Chicago route information
Origin airport
Region of Waterloo Intl.
Destination airport
O'Hare Intl.
Return price
S$258
Distance
631 km

Perfect flights from Kitchener to Chicago

Your Journey from Kitchener to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from Kitchener 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 Air Canada. Our selection of flights from Region of Waterloo Intl. to O'Hare Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Kitchener to Chicago Flights

Experience the joy of finding cheap flights from Region of Waterloo Intl. to O'Hare Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$161 and roundtrip prices from S$258*.
 

Pre-Flight Essentials

Ensure a smooth journey from Kitchener 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 Kitchener 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 Kitchener 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 Kitchener 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 Kitchener 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 YKF to O'Hare Airport?
Start packing your suitcase, because round-trip journeys between Kitchener/Waterloo Airport and ORD start from S$258. That's based on airfares available within the last 7 days on Expedia for flights departing within the next year. Prices can move quickly, so book today to score the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Kitchener/Waterloo Airport to ORD?
We get that things come up unexpectedly, so we've made it as easy as possible for you to cancel your trip online. Just visit the Customer Service Portal and follow the instructions.
How do I find cheap flights from YKF to O'Hare Airport 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 Region of Waterloo Intl. Airport (YKF) to O'Hare Intl. Airport (ORD) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from YKF to O'Hare Airport?
That new movie you've been wanting to see will have to wait — the flight distance between YKF and O'Hare Airport is only 640 kilometres. The captain will be asking you to put your seat upright for landing before you know it.
Which airlines fly direct from YKF to O'Hare Intl. Airport (ORD)?
Flying directly between Kitchener/Waterloo Airport and ORD isn't possible at present. However, you'll still be able to find a flight to Chicago with at least one stop.
Are Region of Waterloo Intl. Airport (YKF) to O'Hare Airport flight tickets cheaper when they're purchased at the last minute?
Booking your trip from Kitchener/Waterloo Airport to ORD at the last minute could save you some serious cash. However, you might miss out on a flight altogether! If you'd rather not take any chances, book well ahead of your departure date. In fact, Expedia has some of the biggest bargains up to a year in advance. If your preferred carrier hasn't released tickets yet, check back frequently as deals are updated all the time on Expedia.

Explore a world of travel with Expedia

*Available to Expedia members.