Cheap Flights from Kitchener / Waterloo (YKF) to Chicago (CHI)

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 round-trip flight from Kitchener / Waterloo to Chicago? Find the lowest prices on one-way and round-trip tickets right here.

Chicago.$1,064 per passenger.Departing Thu, May 23, returning Mon, May 27.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Kitchener / Waterloo on Thu, May 23, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departing from Chicago O'Hare International on Mon, May 27, arriving in Kitchener / Waterloo.Price includes taxes and charges.From $1,064, select.

Chicago.$1,135 per passenger.Departing Fri, May 31, returning Mon, Jun 3.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Kitchener / Waterloo on Fri, May 31, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departing from Chicago O'Hare International on Mon, Jun 3, arriving in Kitchener / Waterloo.Price includes taxes and charges.From $1,135, select.

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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.

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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 found	$1,064
Cheapest month to fly	May
Average flights per week	0

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 round-trip flight from Kitchener / Waterloo to Chicago is $1,064. 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 $1,064.
: There are no flights flying from Kitchener / Waterloo to Chicago, as of April 2024.
: 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 15.8 miles away from the center of Chicago. We've found flights to this airport from $1,064.
: After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Kitchener / Waterloo Airport to Chicago on Thursday, May 23, 2024.
: 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 46°F. July is typically the warmest month in Chicago, when it usually averages around 80°F. You can expect the least rain in January. The coldest month is January, with temperatures averaging 18°F. The rainiest month is August.
: Currently, WestJet offers the cheapest flight tickets to Chicago.

How to find cheap flights to Chicago from Kitchener / Waterloo

Looking for cheap tickets from Kitchener / Waterloo to Chicago? 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 Delta Air Lines 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. And with us, there are no hidden fees – what you see is what you pay.
Compare flight deals to Chicago from Kitchener / Waterloo from over 1,000 providers. Then choose the cheapest plane tickets or fastest journeys.
Flex your dates to find the best Kitchener / Waterloo–Chicago ticket prices. If you're 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 from Kitchener / Waterloo.
Set up a Price Alert. You can easily track the fare of your cheap Kitchener / Waterloo–Chicago 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.
Fly without stops. Only interested in direct flights between Kitchener / Waterloo and Chicago? 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. 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 stumble on 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 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 the next time you travel.

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

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

Plan the rest of your trip from Toronto to Chicago

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