Cheap Flights from Chicago (CHIA) to Kitchener / Waterloo (YKF)

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Find the cheapest month or even day of the year to fly to Kitchener / Waterloo

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Flight deals from Chicago to Kitchener / Waterloo

Looking for a cheap last-minute deal or the best return flight from Chicago to Kitchener / Waterloo Airport? If you want to travel next month, return fares start from £463. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago to Kitchener / Waterloo

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

Chicago to Toronto: Flight information

The things to know before you go.
Cheapest flight found£191
Cheapest month to flyJuly

Finding cheap flights from Chicago to Kitchener / Waterloo: Frequently asked questions

The best price we found for a return flight from Chicago to Kitchener / Waterloo is £426. 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.
Currently, there are no airlines that fly direct from Chicago to Kitchener / Waterloo. But we found flights with one stop from £426.
As of June 2026, there are no flights flying from Chicago to Kitchener / Waterloo.
The cheapest month to fly from Chicago to Kitchener / Waterloo is usually September.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Kitchener / Waterloo Airport on Friday, 4 September 2026.
No airlines currently offer direct flights between Chicago and Kitchener / Waterloo Airport. Most routes have one or more stops.
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 Kitchener / Waterloo 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 Toronto is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Kitchener / Waterloo is WestJet .

Travelling from Chicago to Region of Waterloo International Airport (YKF): What you need to know

  • The timezone in Toronto is UTC-5, which is one hour ahead of Chicago. Region of Waterloo International Airport is located in Toronto.

  • To ensure you get on your flight from Chicago to YKF, allow plenty of time to check in and drop off your luggage. Arriving two hours before international departures and an hour before domestic flights is the standard rule.

  • July is a popular time to fly out. If you're heading away then or around a major holiday like Fourth of July, show up even earlier. Aim for at least two hours ahead for domestic flights and as much as four hours for international journeys.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • You might be able to make your cheap flight from Chicago to YKF even cheaper with a stopover. Just deselect 'Direct flights only' during your search to find which cities you could pass through. Calgary International Airport (YYC) is an option when taking off from Chicago O'Hare International Airport (ORD).

  • Located around 27 kms (17 miles) from the centre of Chicago, ORD can be reached in about 30 minutes by car (depending on traffic). The journey on public transport is roughly 45 minutes.

  • Searching for a convenient hotel close to Chicago O'Hare International Airport? If you've booked an early flight from Chicago to Region of Waterloo International Airport, these accommodation options will put you moments from check-in:

  • 75% of flights that leave from Chicago O'Hare International Airport arrive at their destination on time.

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

Chicago Midway International Airport (MDW)

  • You can arrive at MDW from the centre of Chicago in about 25 minutes by car, depending on traffic conditions. The ride by public transport takes roughly 30 minutes to travel the 16 kms (10 miles) or so.

  • Got a crack-of-dawn departure? Think about checking in to one of these accommodation options near Chicago Midway International Airport the day before your Chicago to YKF flight:

  • Looking at how often flights stay on schedule, Chicago Midway International Airport has an on-time arrival performance of 77%.

  • The address for MDW is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • From the centre of Chicago, RFD is around 145 kms (90 miles) away. It'll take you roughly 1 hour 40 minutes to arrive by car and 2 hours or so on public transport.

  • Make catching an early Chicago to Region of Waterloo International Airport flight the easiest part of your journey. Stay at one of these accommodation options close to Chicago Rockford International Airport and head to your check-in counter without rushing:

  • Airports have an on-time performance rating that measures how often flights get to their destinations without delays. At RFD, that rate is 76%.

  • The address of Chicago Rockford International Airport is 2 Airport Cir.

About Region of Waterloo International Airport (YKF)

Getting from Region of Waterloo International Airport (YKF) to central Toronto

  • Region of Waterloo International Airport is around 97 kms (60 miles) from the centre of Toronto. It takes around 1 hour 10 minutes or so to drive to the city.

  • It'll take around 2 hours if you're travelling by public transport.

How to find the cheapest flights from Chicago to Region of Waterloo International Airport (YKF)

  • Currently, £191 is the lowest price we've found for a one-way ticket from Chicago to Region of Waterloo International Airport. The cheapest price for a return flight is £427. Remember fares can change due to demand at the time of booking.

  • Booking in advance is often the key to finding a cheap flight from Chicago to YKF. Flight prices rise as demand increases, so the closer you get to departure, the more it could cost you.

  • Cheap Chicago to Region of Waterloo International Airport tickets are easier to find when your dates are flexible. Try using the 'Whole month' search function to compare fares across each month and then fly out on the cheapest day.

  • Never miss a deal on plane tickets from Chicago to YKF by creating a Price Alert. We'll send you an email or push notification on the app when fares go down.

  • Filters make it easier to save some cash on your flight from Chicago to Region of Waterloo International Airport. Choose the departure times, airlines and number of stops that work for you. Then sort the results by 'Cheapest' to zero in on the cheapest fare fast.

The best time to fly from Chicago to Region of Waterloo International Airport (YKF)

  • It's time to figure out your travel dates for your flight from Chicago to Region of Waterloo International Airport (YKF). July is the busiest month to travel to Toronto. If crowds aren't your thing, head there in November.

  • The warmest month in Toronto is July, with temperatures ranging between 14ºC and 28ºC. Book your Chicago to YKF plane ticket then if that's your definition of good weather.

  • January has temperatures of between -12ºC and 1ºC. Search for cheap tickets from Chicago to Region of Waterloo International Airport around that time if you like travelling in cooler conditions.

More about Toronto

  • Once you've booked your flight from Chicago to Region of Waterloo International Airport, choose a hotel that puts you where you want to be. Make one of these accommodation options your base for exploring Toronto:

  • CN Tower and The Top CN Tower are just two of the top attractions to put on your Toronto itinerary. Continue your sightseeing adventures at Royal Ontario Museum.

Explore more of Canada

  • You've visited Toronto, now it's time to explore other parts of Canada. Travel about 88 kms (55 miles) southwest to London to check off its top attractions. From Forks of the Thames River to Falls View Park and Fanshawe Pioneer Village, your itinerary will be busy.

  • Around 322 kms (200 miles) east of Toronto, Kingston is another essential stop in Canada. Experience this destination's highlights firsthand at Fort Henry, Rideau Canal - Jones Falls Defensible Lockmasters House and Kingston Penitentiary.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.