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 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 October.

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 foundC$147
Cheapest month to flyOctober

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 C$280. 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 C$280.
As of September 2025, there are no flights flying from Kitchener / Waterloo to Chicago.
The cheapest month to fly from Kitchener / Waterloo to Chicago is usually October.
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 C$280.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Kitchener / Waterloo Airport to Chicago on Saturday, October 18, 2025.
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 September, the average temperature is usually around 18°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.

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

  • Region of Waterloo International Airport is located in Toronto. Operating on the UTC-5 timezone, Chicago is 1 hour behind Toronto.

  • For a stress-free journey, turn up at the airport two hours ahead of international flights and one hour before domestic departures. This will give you plenty of time to catch your flight from YKF to Chicago.

  • Travelling during a peak month such as August? Major public holidays and other popular seasons can lead to longer lines at security. Play things extra safe and arrive up to four hours ahead of an international flight and two hours before domestic departures.

  • If you have a passport from Canada and want to travel to United States for tourism purposes, you won't need a visa. However, entry and visa requirements may vary based on the length and purpose of your stay and are subject to change. For the latest rules, contact your destination's nearest consulate or embassy before reserving a cheap ticket from Region of Waterloo International Airport to Chicago.

  • YKF is around 105 kilometres from central Toronto. If you're catching a cab, driving or ride-sharing from the centre, it'll take 1 hour and 13 minutes or so to get there, depending on traffic conditions. If you're using public transport, expect the travel time to be around 4 hours and 5 minutes.

  • Planning to catch an early flight from Region of Waterloo International Airport to Chicago? Avoid the last-minute rush to the terminal (and sneak in some extra precious sleep) by picking one of these hotels near YKF:

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

  • C$147 is the best price for a one-way ticket from Region of Waterloo International Airport to Chicago. A return flight starts at C$280. These fares may change depending on demand and availability.

  • To pick up cheap tickets from YKF to Chicago, book as early as possible. Airlines usually offer their best fares when flights are first made available.

  • The 'Whole month' search tool shows you the cheapest tickets from Region of Waterloo International Airport to Chicago across the entire month. It's an easy way to snap up a bargain if your travel dates are flexible.

  • Sign into your online account or use the app to set up a Price Alert. We'll notify you straight away if there's a better deal on this route. It's simple to do, and it'll save you the hassle of searching for cheap tickets from YKF to Chicago every day.

  • Make the most of the filters to find your ideal journey. To see the 'Best,' 'Cheapest' or 'Fastest' flights from Region of Waterloo International Airport to Chicago, use the 'Sort by' function. You can also filter results by departure and arrival times, airline, and number of stops.

Airports in Chicago

O'Hare International Airport (ORD)

Chicago Midway International Airport (MDW)

Best time to go to Chicago

  • August is the busiest month to board a flight from Region of Waterloo International Airport to Chicago while February is the quietest. To work out the best time to go to Chicago, consider whether you prefer a lively vibe or a quieter pace.

  • Lock in your flight from Region of Waterloo International Airport to Chicago for July to visit the city during its warmest month. Expect temperatures to range from 15ºC to 29ºC.

  • If you like cooler conditions, look for a cheap flight from YKF to Chicago in January when temperatures average between -12ºC and 3ºC.

More about Chicago

  • Start your Chicago trip right by choosing the perfect place to stay. After booking your flight from Region of Waterloo International Airport to Chicago, browse our range of hotels including:

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

Complete your Chicago trip with a car rental

  • Finding you a cheap flight from Region of Waterloo International Airport to Chicago isn't our only party trick. Check out our car rentals in Chicago and see the sights your way. We find deals from trusted car rental companies and put them all in one place. You can instantly compare rates and then book with no fees.

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