Cheap Flights from Kitchener / Waterloo (YKF) to Chicago Midway (MDW)

How to find cheap flights to Chicago (MDW) from Toronto (YKF) in 2026

Looking for cheap tickets from Kitchener / Waterloo to Chicago Midway? Return tickets start from £607 and one-way flights to Chicago Midway from Kitchener / Waterloo start from £148

Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

• Simply hit 'search'. From British Airways to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Kitchener / Waterloo to Chicago Midway. And with us there are no hidden fees - what you see is what you pay.
• Compare flight deals to Chicago from Toronto from over 1,000 providers. Then choose the cheapest or fastest plane tickets. Flight tickets to Chicago start from £148 one-way.
• Flex your dates to find the best YKF-MDW ticket prices. If you are flexible when it comes to your travel dates, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to Chicago Midway from Kitchener / Waterloo.
• Set up a Price Alert. You can easily track the fare of your cheap Kitchener / Waterloo-Chicago Midway flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
• Flexible on when you travel? The cheapest month to fly from Kitchener / Waterloo to Chicago Midway is April.
• Fly without stops. Only interested in direct flights between Kitchener / Waterloo and Chicago Midway? Make sure to tick 'Direct flights only' when performing a search. If there are direct flights available on the route, these will appear in the results.
• Find the cheapest Business class flights from Kitchener / Waterloo and Chicago Midway. We scour the internet for the best Business, Premium Economy and First Class flight fares to Chicago, too. Check the difference in price as you search – you might just chance upon a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
• Include nearby airports in your search. Widen your search for Kitchener / Waterloo to Chicago Midway flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save next time you travel.
• Search for cheap flights regardless of where you are. To get the best flight booking experience when out and about, download the app and search for plane tickets between Kitchener / Waterloo and Chicago Midway whenever you want.

Combine your flight to Chicago Midway from Kitchener / Waterloo with hotels and car hire

Once you've secured your cheap flight ticket from Kitchener / Waterloo to Chicago Midway, discover the best prices and exclusive rates for hotels in Chicago or nearby. You can also compare hundreds of car hire companies in one go so that you get the best car hire price for your trip.