$106 Cheap flight deals from Chicago (CHI) to Kitchener (YTO)

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This Weekend's Flight Deals from Chicago to Kitchener

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.

Sat, Jul 18 - Sun, Jul 19
ORD
O'Hare Intl.
YKF
Region of Waterloo Intl.
$449 Roundtrip, found 1 day ago
$449
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sat, Jul 18 from O'Hare Intl. to Region of Waterloo Intl., returning Sun, Jul 19, priced at $449 found 1 day ago
Fri, Jul 17 - Mon, Jul 20
MDW
Midway Intl.
YYZ
Pearson Intl.
$461 Roundtrip, found 4 days ago
$461
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Jul 17 from Midway Intl. to Pearson Intl., returning Mon, Jul 20, priced at $461 found 4 days ago
Sun, Jul 19 - Fri, Jul 24
ORD
O'Hare Intl.
YTZ
Billy Bishop Toronto City
$462 Roundtrip, found 21 hours ago
$462
Roundtrip
found 21 hours ago
Select Air Canada flight, departing Sun, Jul 19 from O'Hare Intl. to Billy Bishop Toronto City, returning Fri, Jul 24, priced at $462 found 21 hours ago
Sat, Jul 18 - Tue, Jul 21
MDW
Midway Intl.
YTZ
Billy Bishop Toronto City
$466 Roundtrip, found 1 hour ago
$466
Roundtrip
found 1 hour ago
Select Air Transat flight, departing Sat, Jul 18 from Midway Intl. to Billy Bishop Toronto City, returning Tue, Jul 21, priced at $466 found 1 hour ago

Airfares from $106 One Way, $231 Round Trip from Chicago to Kitchener

Prices starting at $231 for return flights and $106 for one-way flights to Kitchener were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Nov 1 - Thu, Nov 5
ORD
Chicago
YTZ
Toronto
$231 Roundtrip, found 5 days ago
$231
Roundtrip
found 5 days ago
Select Air Canada flight, departing Sun, Nov 1 from Chicago to Toronto, returning Thu, Nov 5, priced at $231 found 5 days ago
Tue, Sep 29 - Thu, Oct 1
ORD
Chicago
YYZ
Toronto
$240 Roundtrip, found 8 hours ago
$240
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Tue, Sep 29 from Chicago to Toronto, returning Thu, Oct 1, priced at $240 found 8 hours ago
Tue, Sep 15 - Thu, Sep 17
ORD
Chicago
YYZ
Toronto
$240 Roundtrip, found 2 days ago
$240
Roundtrip
found 2 days ago
Select United flight, departing Tue, Sep 15 from Chicago to Toronto, returning Thu, Sep 17, priced at $240 found 2 days ago
Sun, Nov 1 - Tue, Nov 10
ORD
Chicago
YTZ
Toronto
$255 Roundtrip, found 3 days ago
$255
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Sun, Nov 1 from Chicago to Toronto, returning Tue, Nov 10, priced at $255 found 3 days ago
Tue, Sep 15 - Thu, Sep 17
ORD
Chicago
YTZ
Toronto
$255 Roundtrip, found 2 days ago
$255
Roundtrip
found 2 days ago
Select Air Canada flight, departing Tue, Sep 15 from Chicago to Toronto, returning Thu, Sep 17, priced at $255 found 2 days ago

Kitchener economy flight packages

Price found within the past 48 hours. Click for updated prices.
1 Hotel Toronto
5.0-star property

1 Hotel Toronto

9.6/10 Exceptional! (751 reviews)

Aug 29 - Sep 1

3 night stay

Chicago (ORD) to Toronto (YYZ)

Air Canada • Coach

Toronto (YYZ) to Chicago (ORD)

American Airlines • Coach
Price was $1,515, price is now $984 per person
$984
per person
found 1 day ago
A beautiful hotel! The entire staff was kind, skilled, and professional. Jonah greeted us when we arrived and made my son and I feel welcome and special. Both the rooftop and lobby bars were perfect. The rooms are cozy, clean, and modern. I love this place and will definitely stay there when I go back to Toronto. If you’re even considering this hotel just book it. You won’t be disappointed!

Reviewed on Jul 10, 2026

Shangri-La Toronto
5.0-star property

Shangri-La Toronto

9.6/10 Exceptional! (1,287 reviews)

Sep 1 - Sep 5

4 night stay

Chicago (CHI) to Toronto (YYZ)

Air Canada • Non-stop • Coach

Toronto (YYZ) to Chicago (CHI)

Porter Airlines • Non-stop • Coach
Price was $1,789, price is now $1,201 per person
$1,201
per person
found 1 day ago
Amazing experience, great service.

Reviewed on Jul 13, 2026

Four Seasons Hotel Toronto
5.0-star property

Four Seasons Hotel Toronto

9.6/10 Exceptional! (969 reviews)

Aug 15 - Aug 23

8 night stay

Chicago (CHI) to Toronto (YYZ)

Delta • Non-stop • Coach

Toronto (YYZ) to Chicago (CHI)

Air Canada • Non-stop • Coach
Price was $4,211, price is now $3,042 per person
$3,042
per person
found 1 hour ago
The room design is excellent The hotel es to calm for my taste For a four seasons level, the staff service usually is excepcional, this was standard just good. Anything you will ask they attended but didn’t anticipate clients needs

Reviewed on Jul 10, 2026

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More About Flying To Kitchener from Chicago

Route Information for Flights from Chicago to Kitchener

Origin Airport IATA Code
CHI
Destination Airport IATA Code
YTO
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Kitchener

Chicago to Kitchener flights are offered at fantastic discount by Orbitz. Book air tickets now and cut those extra costs out of your travel budget to ensure a rewarding travel experience. With guaranteed low prices like these, can you afford to miss this discount?

Book cheap flights from Chicago to Kitchener

Cheap airfares are available on flights from Chicago to Kitchener. Use Orbitz to find the best flights that suit both your budget and the travel times that you need. Travelers who are looking for discounted rates on domestic or international flights need to look no further than Orbitz.

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Get a great package with your Chicago to Kitchener flights

With frequent updates on your flight status, including delays and changes in bookings, traveling becomes more hassle-free than ever. Not only do we offer huge discounted deals on flights from Chicago to Kitchener, we also have fantastic savings on vacation packages, hotel room, cruises, activities, and car rentals so you can pick and choose and create the best travel package for you.

Frequently asked questions

Are there non-stop flights from Chicago to Kitchener?
You betcha. In fact, there are 3 airlines that fly direct from O'Hare Airport to Toronto, ON (YYZ-Pearson Intl.). Book a ticket with one of these top carriers:

  • Air Canada
  • United Airlines
  • American Airlines

What is the shortest flight from Chicago to Kitchener?
It can take as little as 1 hour and 35 minutes to get from ORD to Toronto, ON (YYZ-Pearson Intl.). Sit back and enjoy the service, because you'll be coming in to land in a flash.
What airlines fly from Chicago to Kitchener most frequently?
There are a couple of airlines offering frequent flights from ORD to Pearson Intl. Airport (YYZ), including Air Canada (AC). Popular with travelers, it operates 152 flights on this route every month. Also look into the rewarding deals available with United Airlines (UA). Offering 95 flights each month between Chicago and Kitchener, they make the journey just as enjoyable as the destination.
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 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. 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 from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.