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This Weekend's Flight Deals to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fares from $114 One Way, $169 Round Trip from Kitchener to Chicago

Prices starting at $169 for return flights and $114 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

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More About Flying To Chicago from Kitchener

Route Information for Flights from Kitchener to Chicago

Origin Airport IATA CodeYTO
Destination Airport IATA CodeCHI
Distance436 mi
Direct Flight AirlinesAmerican Airlines, Air Canada, Alaska Airlines, JAL, Aer Lingus, Qantas, Royal Jordanian, Copa Airlines, Air New Zealand, United Airlines
Earliest Flight Arrival12:50PM UTC
Latest Flight Arrival8:44PM UTC

Flights Review

Dec 30, 2019

What could have turned into a nightmare with delays, transitioned smoothly thanks to United. Unlike my horrible experience with AA earlier that week.

Nov 28, 2019

Staff during the flight very friendly. But after arriving in Toronto all staff of AirCanada seemed to be in a hurry and couldn't spend one second in helping me find my gate. When I asked help many of them were very rude, but not all of them.

Nov 26, 2019

Love Porter Airlines!

Oct 6, 2019

Air Canada has always been great to my family.

Sep 30, 2019

Yes, I strongly dislike having to pay for my bag. I’d prefer one free checked bag and charge for second bag. You want customers to fly your airline and travelers need luggage so figure out a better way.

Jul 30, 2019

Thanks for great service!

Jun 16, 2019

Just late leaving Toronto so just barely made it to my connection.

Dec 1, 2018

Will continue to fly with United Airlines for future trips

Oct 2, 2018

Porter is great

Sep 19, 2018

My husband’s missing luggage was delivered one day after we returned home. As it was not delivered within the four hour window, he tried to call to find out the status of delivery, but only heard recording message. He practically waited the whole time at home and listened for door bell ringing. Despite the delay in getting his luggage, we had positive experience flying Porter for the first time.

Kitchener to Chicago

Orbitz can provide you with the greatest deals on a wide range of Kitchener to Chicago flights. Orbitz offers guaranteed low prices and offers you the convenience of cutting-edge mobile tools thus providing you with your best travel experience ever.

Mobile Apps for Kitchener to Chicago Flights

You can use our mobile app to find the cheapest prices for flights from Kitchener to Chicago. With this cutting-edge technology, you can check up on your flight’s status, gate number and luggage claim handling, and reserve exclusive deals on top hotels at short notice.

Loyalty Rewarded

For travelers who regularly book Kitchener to Chicago flights, our frequent flyer program offers even more low-cost air tickets. You will be able to store your miles in your personal Orbitz account and add them with ease to your future reservations.

Trouble-Free Traveling With Flight Alerts

Orbitz will not only provide you with the assistance that you require when purchasing flights from Kitchener to Chicago but will ensure that you remain fully updated on any flight delays, changes or disruptions by providing free alerts. Your Kitchener to Chicago flights alerts can be sent directly to your phone or email. You can also opt for these alerts to be sent to your family and friends so that everyone is kept informed of your travel plans.

 Budget Flying Made Simple

Finding cheap flights from Kitchener to Chicago is easy with Orbitz. You can pick and choose airlines for your international flights to create inexpensive yet convenient travel arrangements.

Flights from Kitchener to Chicago - Frequently Asked Questions

What is the shortest flight from Kitchener to Chicago?

Jetting from Kitchener, ON (YKF-Region of Waterloo Intl.) to Chicago, IL (ORD-O'Hare Intl.) will take you at least 7 hours and 24 minutes. Savor a wine and read a few magazines — it's the ideal opportunity to simply relax.

If I am not able to travel due to COVID-19, can I cancel my flight to Chicago?

We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.

Are there flights to Chicago with flexible change policies?

In most cases you'll have the option to reschedule your flight to Chicago without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.

What is the cheapest day of the week to fly?

Consider flying out early in the week to save on your airfare. Orbitz data from 2019 shows that Tuesday is the cheapest day to depart, followed by Monday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.

What is the cheapest month to fly?

We won't keep you guessing, according to Orbitz data the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a fresh start to the new year. Be aware that the most expensive time to fly isn't the height of summer, as most people assume, but the festive month of December.

How can I save money on flights?

To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2019 saved over 50% on their airfares. Get mixing and matching today!

*According to flight demand on Orbitz.com from January to December 2019. Savings are subject to change based on departure location, date and destination.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.