$64 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, Nov 15 - Tue, Nov 18
ORD
O'Hare Intl.
YKF
Region of Waterloo Intl.
$392 Roundtrip, found 3 days ago
$392
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Sat, Nov 15 from O'Hare Intl. to Region of Waterloo Intl., returning Tue, Nov 18, priced at $392 found 3 days ago
Fri, Nov 14 - Sun, Nov 23
MDW
Midway Intl.
YTZ
Billy Bishop Toronto City
$403 Roundtrip, found 4 days ago
$403
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Fri, Nov 14 from Midway Intl. to Billy Bishop Toronto City, returning Sun, Nov 23, priced at $403 found 4 days ago
Fri, Nov 14 - Mon, Nov 24
MDW
Midway Intl.
YYZ
Pearson Intl.
$435 Roundtrip, found 5 days ago
$435
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Nov 14 from Midway Intl. to Pearson Intl., returning Mon, Nov 24, priced at $435 found 5 days ago
Sun, Nov 16 - Tue, Nov 18
ORD
O'Hare Intl.
YYZ
Pearson Intl.
$556 Roundtrip, found 11 hours ago
$556
Roundtrip
found 11 hours ago
Select Porter Airlines flight, departing Sun, Nov 16 from O'Hare Intl. to Pearson Intl., returning Tue, Nov 18, priced at $556 found 11 hours ago

Airfares from $64 One Way, $167 Round Trip from Chicago to Kitchener

Prices starting at $167 for return flights and $64 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.

Mon, Feb 9 - Fri, Feb 13
ORD
Chicago
YYZ
Toronto
$167 Roundtrip, found 3 days ago
$167
Roundtrip
found 3 days ago
Select Air Canada flight, departing Mon, Feb 9 from Chicago to Toronto, returning Fri, Feb 13, priced at $167 found 3 days ago
Fri, Jan 23 - Fri, Jan 30
MDW
Chicago
YTZ
Toronto
$171 Roundtrip, found 1 day ago
$171
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Fri, Jan 23 from Chicago to Toronto, returning Fri, Jan 30, priced at $171 found 1 day ago
Sat, Jan 10 - Sun, Jan 11
ORD
Chicago
YKF
Kitchener
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago
Select Air Canada flight, departing Sat, Jan 10 from Chicago to Kitchener, returning Sun, Jan 11, priced at $177 found 2 days ago
Sat, Jan 10 - Sun, Jan 11
ORD
Chicago
YHM
Hamilton
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago
Select Air Canada flight, departing Sat, Jan 10 from Chicago to Hamilton, returning Sun, Jan 11, priced at $177 found 2 days ago
Sun, Dec 7 - Wed, Dec 10
ORD
Chicago
YYZ
Toronto
$194 Roundtrip, found 4 days ago
$194
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sun, Dec 7 from Chicago to Toronto, returning Wed, Dec 10, priced at $194 found 4 days ago

Kitchener economy flight packages

Price found within the past 48 hours. Click for updated prices.
Delta Hotels by Marriott Toronto Airport & Conference Centre
4.0-star property

Delta Hotels by Marriott Toronto Airport & Conference Centre

8.6/10 Excellent! (1,754 reviews)

Dec 18 - Dec 22

4 night stay

Chicago (CHI) to Toronto (YYZ)

United • Roundtrip • Coach
Price was $584, price is now $413 per person
$413
per person
found 7 hours ago
Friendly service, clean room, easy to find shuttle service. Really appreciated the instructions for the shuttle ahead of time too.

Reviewed on Oct 11, 2025

Hotel Riu Plaza Toronto
4.0-star property

Hotel Riu Plaza Toronto

9.2/10 Wonderful! (172 reviews)

Dec 18 - Dec 22

4 night stay

Chicago (CHI) to Toronto (YYZ)

United • Roundtrip • Coach
Save 100% on your flight
Price was $887, price is now $598 per person
$598
per person
found 7 hours ago
Great hotel!! The breakfast and chef was amazing. I did however book my room over a month ago a selected the deluxe room that was available but on the day of the trip, I was assigned a handicap room & was told that I booked last minute and that was only left?? I spoke to the hotel manager and she fixed it right away! despite that, I would always recommend this place in the future.

Reviewed on Oct 28, 2025

1 Hotel Toronto
5.0-star property

1 Hotel Toronto

9.4/10 Exceptional! (620 reviews)

Dec 14 - Dec 17

3 night stay

Chicago (MDW) to Toronto (YYZ)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,166, price is now $815 per person
$815
per person
found 1 day ago
Very unique, warm and cozy décor. Very pleasant and accommodating staff. Enjoyed ourselves immensely even though it was for business.

Reviewed on Oct 31, 2021

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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

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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.

More Destinations

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.