Cheap Flights from Toronto (YKF) to Chicago (ORD)

Compare Kitchener / Waterloo to Chicago O'Hare International flight deals

Find the cheapest month or even day of the year to fly to Chicago O'Hare International

Book the best Chicago O'Hare International fare with no extra fees

Flight deals from Kitchener / Waterloo to Chicago O'Hare International

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

Find the cheapest month to fly from Kitchener / Waterloo to Chicago O'Hare International

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

Kitchener / Waterloo to Chicago O'Hare International: Alternative routes

Compare routes from Kitchener / Waterloo to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago O'Hare International.

Toronto to Chicago: Flight information

The things to know before you go.
Cheapest flight found$443
Cheapest month to flySeptember

Finding cheap flights from Kitchener / Waterloo to Chicago O'Hare International: Frequently asked questions

The best price we found for a return flight from Kitchener / Waterloo to Chicago O'Hare International is $443. 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 O'Hare International. But we found flights with one or more stops from $443.
As of August 2025, there are no flights flying from Kitchener / Waterloo to Chicago O'Hare International.
The cheapest month to fly from Kitchener / Waterloo to Chicago O'Hare International is usually September.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Kitchener / Waterloo Airport to Chicago O'Hare International Airport on Friday, 19 September 2025.
No airlines currently offer direct flights between Kitchener / Waterloo Airport and Chicago O'Hare International Airport. 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 O'Hare International 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.
Currently, Flair Airlines offers the cheapest flight tickets to Chicago O'Hare International.

Travelling from Region of Waterloo International Airport (YKF) to O'Hare International Airport (ORD): what you need to know

  • Chicago's timezone is UTC-5, making Chicago one hour behind Toronto.

  • Leave plenty of time to make your YKF to ORD flight. As a rule of thumb, arrive at least two hours before international departures and an hour ahead for domestic flights.

  • You can expect longer queues in popular months like August. Arriving up to four hours ahead of international flights and two hours for a domestic departure is a smart move.

How to find the cheapest flights from Region of Waterloo International Airport (YKF) to O'Hare International Airport (ORD)

  • Right now, $234 is the cheapest price we've found for a one-way Region of Waterloo International Airport to O'Hare International Airport flight. The best price for a return ticket is $443. Bear in mind that fares may change due to demand at the time of booking.

  • It's usually smart to book early if you want to get cheap tickets from YKF to ORD. That's because flight prices are based on demand, which tends to increase closer to departure.

  • Finding cheap flights from Region of Waterloo International Airport to O'Hare International Airport is more likely if you can be flexible with your travel dates. Use the 'Whole month' search tool to see the lowest fares across each month and score a great deal.

  • There's no need to check back in every day to see if fares have gone down when you create a Price Alert. We'll let you know as soon as a special offer becomes available on cheap flights from YKF to ORD.

  • Discover the ideal flight for you by using the filters. To see the 'Fastest,' 'Best' or 'Cheapest' flights from Region of Waterloo International Airport to O'Hare International Airport, use the 'Sort by' function. You can also filter by arrival and departure times, airline, and journey duration.

Handy information about Region of Waterloo International Airport (YKF)

  • When it comes to the on-time performance of Region of Waterloo International Airport, data shows 63.64% of flights meet their scheduled arrival time.

  • To reach Region of Waterloo International Airport from central Toronto, it'll take about 1 hour 15 minutes if you're going by car. Of course, this depends on traffic conditions. It's approximately 105 kilometres from the airport to the city centre.

  • The journey when using public transport takes about 4 hours 5 minutes.

  • Get your trip off to a stress-free start by staying near YKF. Whether you have an early flight from Region of Waterloo International Airport to O'Hare International Airport or just don't want to be rushed, these hotels are the answer:

Arriving at O'Hare International Airport (ORD)

Getting from O'Hare International Airport (ORD) to central Chicago

  • You'll find ORD at 10000 West O'Hare.

  • From O'Hare International Airport, Chicago is approximately 40 kilometres away. It takes around 35 minutes to drive to the centre.

  • It takes around 55 minutes if you're using public transport.

When to fly to O'Hare International Airport (ORD)

  • August is the busiest month for flights from Region of Waterloo International Airport to O'Hare International Airport. For a quieter experience, travel to Chicago in January.

  • The warmest month in Chicago is July, with the temperature ranging between 15ºC (59ºF) and 29ºC (84ºF). Book your flights from Region of Waterloo International Airport to O'Hare International Airport in this month if this is the type of weather you enjoy.

  • January has average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for cheap tickets from YKF to ORD sometime then if you want to travel when it's cooler.

Explore more of United States

  • Chicago has plenty to offer, but there are so many other corners of United States you'll want to see. About 451 kilometres south-east of Chicago, a visit to Columbus will keep your itinerary packed. Start with leading attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • If you're ready to explore another great destination in United States, consider Indianapolis, about 257 kilometres south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are key reasons to visit.

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