444 € Cheap Flights from Kitchener / Waterloo to Chicago

Compare Kitchener / Waterloo to Chicago flight deals

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Flight deals from Kitchener / Waterloo to Chicago

Looking for a cheap last-minute deal or the best return flight from Kitchener / Waterloo to Chicago? Find the lowest prices on one-way and return tickets right here.

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

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

Alternative Kitchener / Waterloo to Chicago routes

Looking for the cheapest, fastest or easiest route from Kitchener / Waterloo to Chicago? You could fly into the following airports instead.

Toronto to Chicago: Flight information

The things to know before you go.
Cheapest flight found444 €
Cheapest month to flyApril

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

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Kitchener / Waterloo to Chicago is 444 €. 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 Kitchener / Waterloo to Chicago. But we found flights with one or more stops from 444 €.
As of February 2026, there are no flights flying from Kitchener / Waterloo to Chicago.
The cheapest month to fly from Kitchener / Waterloo to Chicago is usually April.
If you're flying from Kitchener / Waterloo Airport, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the centre of Chicago. We've found flights into this airport from 444 €.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Kitchener / Waterloo Airport to Chicago on Monday, 6 April 2026.
No airlines currently offer direct flights between Kitchener / Waterloo Airport and Chicago. 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 Chicago 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 Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In February, the average temperature is usually around -2°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, WestJet offers the cheapest flight tickets to Chicago.

Flying from Region of Waterloo International Airport (YKF) to Chicago: what you need to know

  • Region of Waterloo International Airport is located in Toronto. Following the UTC-5 timezone, Chicago is one hour behind Toronto.

  • Allow plenty of time to catch your YKF to Chicago flight. It's generally best to arrive at least two hours before international departures and an hour ahead for domestic flights.

  • Heading away during a peak time like a bank holiday? Expect longer queues at check-in and security. To be on the safe side, arrive up to four hours before international flights and two hours ahead of domestic departures.

  • The journey from central Toronto to YKF takes about 4 hours 5 minutes by public transport. If you ride-share, drive or take a cab, you'll cover the 80 kilometres in 1 hour 15 minutes or so, depending on traffic conditions.

  • Want an easy start to your journey? Stay near YKF. Whether you're taking an early flight from Region of Waterloo International Airport to Chicago or just don't want to be rushed, these hotels are all about convenience:

  • When it comes to the on-time performance of Region of Waterloo International Airport, data shows 63.64% of flights arrive within the scheduled time frame.

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

  • The best price we've seen for a one-way Region of Waterloo International Airport to Chicago flight is 174 €. The cheapest price for a return flight is 444 €. Remember fares may change due to availability at the time of booking.

  • Booking ahead of time is often the key to scoring a cheap flight from YKF to Chicago. Flight prices rise as demand increases, so the nearer you get to departure, the more it could cost you.

  • Landing cheap tickets from Region of Waterloo International Airport to Chicago is more likely if you can be flexible with your travel plans. Use the 'Whole month' tool to get the best prices across every month and walk away with a fantastic deal.

  • Save time looking for cheap flights from YKF to Chicago by creating a Price Alert. We'll send you an email or push notification on the app when a new discounted fare appears.

  • Tailor your flights with filters. Pick your preferred arrival and departure times, airlines and total journey duration. You can also sort your results by 'Fastest,' 'Best' or 'Cheapest' flights from Region of Waterloo International Airport to Chicago.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) is around 40 kilometres from central Chicago. If you're opting for a ride-share or a cab, the drive will take roughly 35 minutes.

  • If you're travelling on public transport, expect a journey time of around 55 minutes.

  • If you have a late flight from Region of Waterloo International Airport to Chicago, few things beat the convenience of staying close to the terminal. Pick up your bags from the carousel and then be showered and resting not long after at one of these hotels near ORD:

  • Grab an O'Hare International Airport rental car and discover Chicago and beyond with your own wheels. Routes Car Rentals, Dollar and Budget are well-known companies you can book with here.

  • For the best deal, book your ride from O'Hare International Airport about four weeks ahead of your flight from YKF to Chicago.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Central Chicago is around 19 kilometres from Chicago Midway International Airport (MDW). After your flight from Region of Waterloo International Airport to Chicago has hit the runway and you've made your way out of the airport, the drive should take about 20 minutes.

  • The journey will take about 45 minutes on public transport.

  • There are some comfortable places to rest your head close to MDW. Kick back and get cosy after your YKF to Chicago flight at one of these well-located options:

  • Dollar, Hertz and Budget make collecting a Chicago Midway International Airport rental car simple. These trusted providers are located in or around the terminal and will have you on your way in a heartbeat.

  • Avoid paying extra. Booking your ride four weeks before your arrival at MDW will help you save.

  • The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Hop off your flight from Region of Waterloo International Airport to Chicago and make your way to your hotel or jump right into exploring. Central Chicago is around 137 kilometres from Chicago Rockford International Airport (RFD) and typically takes 1 hour 25 minutes to reach driving.

  • Public transport can get you there in about 4 hours 15 minutes.

  • If you don't want to make the trip to the centre, find a hotel close to RFD. Check in to one of these options after your YKF to Chicago flight:

  • Be in the driver's seat of the next part of your journey by picking up a Chicago Rockford International Airport rental car. Budget, Alamo and National are some companies you can book with.

  • Rental companies sometimes offer promotions for early bookings, so book your vehicle from RFD well ahead of your flight from Region of Waterloo International Airport to Chicago. A bit of planning goes a long way for your wallet.

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

Best time to go to Chicago

  • Carefully consider your dates before locking in your flight from Region of Waterloo International Airport to Chicago. The city buzzes in high season, but rates are generally higher and attractions can get crowded. Go to Chicago in low season for a quieter vibe.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC (59ºF) and 29ºC (84ºF). Lock in your Region of Waterloo International Airport to Chicago plane ticket then if that's your definition of good weather.

  • January sees average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Search for a cheap ticket from YKF to Chicago around that time if you like travelling in cooler conditions.

More about Chicago

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

  • There are so many things to do and see in this city it can be tricky to work out where to begin. Art Institute of Chicago, Millennium Park and LandShark Beer Garden at Navy Pier are major attractions which should be on every Chicago itinerary.

Explore more of United States

  • Chicago has its own special appeal, but there are so many other corners of United States waiting to be explored. Around 451 kilometres south-east of Chicago, a trip to Columbus will keep your itinerary packed. Start with leading sights like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another must-experience destination in United States and is around 257 kilometres south-east of Chicago. No trip is complete without dropping by The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.