Cheap Flights from Kitchener / Waterloo to Chicago

Compare Kitchener / Waterloo to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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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 Airport to Chicago? If you want to travel next month, return fares start from Rs193,395. 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 May.

Toronto to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRs70,164
Cheapest month to flyMay

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 Rs158,715. 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 Rs158,715.
As of April 2026, there are no flights flying from Kitchener / Waterloo to Chicago.
The cheapest month to fly from Kitchener / Waterloo to Chicago is usually May.
If you're flying from Kitchener / Waterloo Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from Rs158,715.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Kitchener / Waterloo Airport to Chicago on Friday, 29 May 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 April, the average temperature is usually around 8°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, Flair Airlines offers the cheapest flight tickets to Chicago.

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

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

  • For a relaxed start to your YKF to Chicago flight, allow plenty of time for things like baggage drop and finding your gate. Turning up two hours ahead of international departures and one hour before domestic flights is the general travel rule.

  • During popular months such as August, it's wise to get to the airport earlier than usual. Arrive two hours before domestic departures and four hours ahead for international flights when you fly during peak periods in general.

  • Located around 80 kilometres from central Toronto, YKF can be reached in about 1 hour 15 minutes by car, depending on traffic. Travelling on public transport will take roughly 4 hours 5 minutes.

  • Booked an early flight from Region of Waterloo International Airport to Chicago? Avoid rushing to the airport (and catch some extra z's) by choosing one of these hotels near YKF:

  • Of the flights that depart from Region of Waterloo International Airport, 63.64% touch down on time at their destination.

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 Rs70,164. The cheapest price for a return flight is Rs158,715. 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) to the centre of Chicago takes about 35 minutes by car. The centre is roughly 40 kilometres away.

  • It'll take around 55 minutes to get there using public transport.

  • The last thing you need is a lengthy journey to your hotel if you're getting in late on a flight from Region of Waterloo International Airport to Chicago. Book one of these accommodation options near ORD instead:

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

  • Booking your vehicle from O'Hare International Airport around four weeks before your flight from YKF to Chicago can help you lock in the best possible rate.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) is roughly 19 kilometres from the centre of Chicago. Once you've disembarked your flight from Region of Waterloo International Airport to Chicago, it'll take you around 20 minutes to get to the heart of the city in a ride-share or cab.

  • You can expect the journey to take roughly 45 minutes on public transport.

  • You'll find some comfortable places to call home for the night near MDW. Unwind and get cosy after your YKF to Chicago flight at one of these well-located options:

  • Dollar, Hertz and Budget make picking up a Chicago Midway International Airport rental car easy and quick. These providers are located in or around the terminal and will have you ready to go in a flash.

  • Get what you want, not just what's left over. Reserving your ride from MDW four weeks ahead of time often means better prices and a greater selection of vehicles.

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

Chicago Rockford International Airport (RFD)

  • Step off your flight from Region of Waterloo International Airport to Chicago and head straight for your hotel or jump right into sightseeing. Central Chicago is around 137 kilometres from Chicago Rockford International Airport (RFD) and usually takes 1 hour 25 minutes to reach by car.

  • If you use public transport, the journey takes about 4 hours 15 minutes.

  • If you don't want to make your way into the centre, head for a hotel near RFD. Check in to one of these stays after your YKF to Chicago flight:

  • Whether you're after a compact for a solo adventure or a spacious SUV to fit the whole crew comfortably, you'll find the ideal Chicago Rockford International Airport rental car for you. Explore the range of wheels available here from providers such as Budget, Alamo and National.

  • If you prefer a certain model or make, booking early increases your chances of finding what you want. Reserve your ride from RFD at least a few weeks ahead of your flight from Region of Waterloo International Airport to Chicago.

  • Chicago Rockford International Airport's address is 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 and 29ºC. Lock in your Region of Waterloo International Airport to Chicago flight ticket then if that's your definition of good weather.

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

More about Chicago

  • When it comes to looking for somewhere to rest your head, you'll find the best places to stay in Chicago right here. Browse these options after you've booked your flight from Region of Waterloo International Airport to Chicago:

  • There are so many things to see and do in this city it can be hard to know where to start. Art Institute of Chicago, Millennium Park and LandShark Beer Garden at Navy Pier are leading attractions which should feature 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.