C$364 Cheap Flights from Chicago (CHIA) to Kitchener / Waterloo (YKF)

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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 C$947. 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 June.

Chicago to Toronto: Flight information

The things to know before you go.
Cheapest flight foundC$364
Cheapest month to flyJune

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 C$925. 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 C$925.
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, September 25, 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

  • Start your vacation planning by considering where you'll catch your flight from Chicago to Region of Waterloo International Airport (YKF). O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are the main airports in Chicago.

  • Toronto is 1 hour ahead of Chicago. Region of Waterloo International Airport is located in Toronto, which operates on the UTC-4 timezone.

  • Give yourself enough time to catch your flight from Chicago to YKF. As a rule of thumb, arrive two hours before international departures and an hour ahead for domestic flights.

  • If you're travelling during a peak month like August, get to the terminal even earlier. You'll want to arrive up to four hours before international flights and two hours ahead of domestic departures. Check-in and security lines will be longer during vacation periods like summer and spring break.

Airports in Chicago

O'Hare International Airport (ORD)

  • Stopovers offer a great opportunity to discover a new place or just take a break during your trip. When searching for a flight from Chicago to YKF, uncheck 'Direct flights only' to check out all potential stops. Calgary International Airport (YYC) is an option if you're leaving from O'Hare International Airport (ORD).

  • ORD is around 40 kilometres from the centre of Chicago. To work out how to get there, use Google Maps. This useful traveller tool will show you the best route and your public transport options.

  • Need a handy hotel close to O'Hare International Airport? If you're boarding an early flight from Chicago to Region of Waterloo International Airport, these accommodation options will have you sleeping moments from your departure gate:

Chicago Midway International Airport (MDW)

About Region of Waterloo International Airport (YKF)

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

  • Region of Waterloo International Airport is approximately 105 kilometres from central Toronto. With a car rental or if you're catching a cab, the drive is about 1 hour and 13 minutes.

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

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

  • C$364 is the lowest price we've seen for a one-way ticket from Chicago to Region of Waterloo International Airport. Return flights start from C$925. Prices may vary depending on availability at the time of booking.

  • Don't leave everything to the last moment. You're more likely to find flight tickets from Chicago to YKF if you book ahead. Airlines often offer some fantastic early bird rates.

  • Finding flight tickets from Chicago to Region of Waterloo International Airport is more likely if you're flexible with your travel dates. Try using the 'Whole month' search tool to see the lowest prices across every month and score a great deal.

  • Create a Price Alert and track any changes on this route through push notifications or email. You'll know straight away when prices go down. Timing matters when searching for flight tickets from Chicago to YKF.

  • Use the filters to tailor your flights from Chicago to Region of Waterloo International Airport. Pick your ideal arrival and departure times, airlines and number of stops. You can also sort your results by 'Cheapest' to find the best deals.

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

  • It's time to plan your trip dates for your flight from Chicago to Region of Waterloo International Airport. August is the most popular month to travel to Toronto. If you prefer a more relaxed vibe, go in May.

  • The warmest month in Toronto is July, with the temperature ranging between 14ºC and 28ºC. Book your flights from Chicago to YKF in this month if this is the type of weather you enjoy.

  • January sees average temperatures of between -12ºC and 1ºC. Search for cheap flights from Chicago to Region of Waterloo International Airport sometime around then if you'd rather travel in cooler conditions.

More about Toronto

  • After locking in your flight from Chicago to Region of Waterloo International Airport, think about where you'll stay in this city. Make one of these accommodation options your base for exploring Toronto:

  • There are so many things to see and do in this city it can be tricky to know where to start. CN Tower, Royal Ontario Museum and Go Tours Canada - Distillery District are top sights which should be on any good Toronto itinerary.

Complete your Toronto trip with a car rental

  • Once you've locked in your hotel and cheap flight from Chicago to Region of Waterloo International Airport, the next task is choosing one of our car rentals in Toronto. Browse the deals and easily compare options on price, fuel policies, and more.

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