Cheap Flights from Chicago to Kitchener / Waterloo

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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? 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 May.

Chicago to Toronto: Flight information

The things to know before you go.
Cheapest flight foundR 2,683
Cheapest month to flyMay

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 R 6,285. 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 R 6,285.
As of February 2026, there are no flights flying from Chicago to Kitchener / Waterloo.
The cheapest month to fly from Chicago to Kitchener / Waterloo is usually April.
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, 24 April 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

  • There are two main airports you can take off from in Chicago. Check out your options departing from O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW) when reserving your flight from Chicago to Region of Waterloo International Airport (YKF).

  • The timezone in Toronto is UTC-4, which is one hour ahead of Chicago. Region of Waterloo International Airport is located in Toronto.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are travel rules to live by. Show up at the airport on time to board your flight from Chicago to YKF.

  • Delays at check-in and security are likely if you're heading away during high season, so allow some extra wiggle room. The recommendation for peak periods? Arrive up to four hours early for international flights and two hours for domestic departures.

Airports in Chicago

O'Hare International Airport (ORD)

  • Stopovers are a great opportunity to visit a new place or just take a break during your trip. When looking for a cheap flight from Chicago to YKF, uncheck 'Direct flights only' to browse all potential stops. Calgary International Airport (YYC) is an option when leaving from O'Hare International Airport (ORD).

  • Located around 40 kilometres from the centre of Chicago, ORD can be reached in about 35 minutes by car, depending on traffic. The journey by public transport takes roughly 55 minutes.

  • Want a stress-free start to your break? Stay near O'Hare International Airport. Whether you have an early flight from Chicago to Region of Waterloo International Airport or want to avoid feeling rushed, these hotels offer the perfect solution:

  • Of all flights departing from O'Hare International Airport, 74.85% arrive on time at their destination.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Using public transport, you can travel from central Chicago to MDW in about 45 minutes. The airport is roughly 19 kilometres away, and making the trip by car will take approximately 20 minutes.

  • Got an early start? Think about staying at one of these hotels near Chicago Midway International Airport the day before your Chicago to YKF flight:

  • When it comes to flight punctuality, Chicago Midway International Airport has an on-time arrival rate of 77.88%.

  • MDW is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • RFD is around 137 kilometres from central Chicago. The drive from the city centre to the terminal takes about 1 hour 25 minutes. If you're considering public transport, expect a journey of around 4 hours 15 minutes.

  • Set yourself up for a smooth departure — stay close to Chicago Rockford International Airport and know you'll get to your gate with time to spare. Settle in at one of these hotels the day before if you've booked an early Chicago to Region of Waterloo International Airport flight:

  • Airports have an on-time performance rating that monitors how often flights get to their destinations when they should. At RFD, that figure is 76.19%.

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

About Region of Waterloo International Airport (YKF)

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

  • The centre of Toronto is about 80 kilometres from Region of Waterloo International Airport. Journey times by car hire or cab will vary depending on traffic conditions and time of day, so do some research ahead of your trip.

  • Travelling on public transport will take you roughly 4 hours 5 minutes.

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

  • R 2,683 is currently the lowest price for a one-way ticket from Chicago to Region of Waterloo International Airport. A return flight starts from R 6,285. These fares can change based on availability and demand.

  • Booking in advance is often the key to scoring a cheap flight from Chicago to YKF. Airlines adjust prices based on demand, so the closer you get to departure, the more you'll likely spend on your ticket.

  • The 'Whole month' search tool will show you the cheapest Chicago to Region of Waterloo International Airport tickets across each month. It's a great way to snap up a bargain if your travel dates aren't set in stone.

  • Locking in a cheap plane ticket from Chicago to YKF couldn't be easier with Price Alerts. All you need to do is set up one of these automatic alerts and we'll let you know when the price has dropped.

  • Lock in a cheap flight from Chicago to Region of Waterloo International Airport by using filters. Select your preferred times, airlines and number of stops, then sort the results by 'Cheapest' for the best deals.

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

  • Think about the kind of holiday you want when planning your trip dates. May is the quietest month to visit Toronto. August is when most people book flights from Chicago to Region of Waterloo International Airport (YKF), which may be ideal if you're after more excitement.

  • When booking your Chicago to YKF plane ticket, consider the kind of weather you prefer. July is the warmest month in Toronto, with temperatures ranging from 14ºC (57ºF) to 28ºC (82ºF).

  • Search for cheap tickets from Chicago to Region of Waterloo International Airport in January if you'd rather travel when it's cooler. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 1ºC (34ºF).

More about Toronto

  • When it comes to looking for somewhere to lay your head, you'll find the top stays in Toronto right here. Explore these hotels once you've booked your flight from Chicago to Region of Waterloo International Airport:

  • Your Toronto trip wouldn't be complete without a bit of sightseeing. Top attractions worth exploring include CN Tower, Skypod CN Tower and Royal Ontario Museum.

Explore more of Canada

  • Toronto has plenty to offer, but there are so many other parts of Canada just waiting to be explored. About 88 kilometres south-west of Toronto, a visit to London will fill your itinerary to the brim. Check out popular attractions like Forks of the Thames River, Falls View Park and Fanshawe Pioneer Village.

  • Kingston is another sought-after destination in Canada and is around 322 kilometres east of Toronto. No trip is complete without experiencing 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 45 days.