$94 Cheap flight deals from Kitchener (YTO) to Chicago (CHI)

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This Weekend's Flight Deals from Kitchener 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.

Fri, Oct 17 - Thu, Nov 6
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
$346 Roundtrip, found 5 days ago
$346
Roundtrip
found 5 days ago
Select Porter Airlines flight, departing Fri, Oct 17 from Billy Bishop Toronto City to Midway Intl., returning Thu, Nov 6, priced at $346 found 5 days ago
Sat, Oct 18 - Sat, Nov 1
YKF
Region of Waterloo Intl.
ORD
O'Hare Intl.
$351 Roundtrip, found 5 days ago
$351
Roundtrip
found 5 days ago
Select Air Canada flight, departing Sat, Oct 18 from Region of Waterloo Intl. to O'Hare Intl., returning Sat, Nov 1, priced at $351 found 5 days ago
Sat, Oct 18 - Sat, Nov 1
YHM
John C. Munro Hamilton Intl.
ORD
O'Hare Intl.
$351 Roundtrip, found 5 days ago
$351
Roundtrip
found 5 days ago
Select Air Canada flight, departing Sat, Oct 18 from John C. Munro Hamilton Intl. to O'Hare Intl., returning Sat, Nov 1, priced at $351 found 5 days ago
Sat, Oct 18 - Sat, Nov 1
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
$356 Roundtrip, found 5 days ago
$356
Roundtrip
found 5 days ago
Select Air Canada flight, departing Sat, Oct 18 from Billy Bishop Toronto City to O'Hare Intl., returning Sat, Nov 1, priced at $356 found 5 days ago

Airfares from $94 One Way, $131 Round Trip from Kitchener to Chicago

Prices starting at $131 for return flights and $94 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.

Fri, Jan 23 - Sun, Jan 25
YTZ
Toronto
MDW
Chicago
$131 Roundtrip, found 3 days ago
$131
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Fri, Jan 23 from Toronto to Chicago, returning Sun, Jan 25, priced at $131 found 3 days ago
Wed, Jan 21 - Sat, Jan 24
YKF
Kitchener
ORD
Chicago
$137 Roundtrip, found 6 days ago
$137
Roundtrip
found 6 days ago
Select Air Canada flight, departing Wed, Jan 21 from Kitchener to Chicago, returning Sat, Jan 24, priced at $137 found 6 days ago
Wed, Jan 21 - Sat, Jan 24
YHM
Hamilton
ORD
Chicago
$137 Roundtrip, found 6 days ago
$137
Roundtrip
found 6 days ago
Select Air Canada flight, departing Wed, Jan 21 from Hamilton to Chicago, returning Sat, Jan 24, priced at $137 found 6 days ago
Wed, Jan 21 - Sat, Jan 24
YYZ
Toronto
ORD
Chicago
$138 Roundtrip, found 6 days ago
$138
Roundtrip
found 6 days ago
Select Air Canada flight, departing Wed, Jan 21 from Toronto to Chicago, returning Sat, Jan 24, priced at $138 found 6 days ago
Thu, Dec 4 - Thu, Dec 11
YYZ
Toronto
ORD
Chicago
$159 Roundtrip, found 1 day ago
$159
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Dec 4 from Toronto to Chicago, returning Thu, Dec 11, priced at $159 found 1 day ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Warwick Allerton - Chicago
4.0-star property

Warwick Allerton - Chicago

8.4/10 Very Good! (2,917 reviews)

Nov 28 - Nov 30

2 night stay

Toronto (YYZ) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to Toronto (YYZ)

Delta • Coach
Price was $460, price is now $375 per person
$375
per person
found 1 day ago
My teen had to fly alone to Chicago and this hotel was so gracious to her!

Reviewed on Oct 5, 2025

Omni Chicago Hotel
4.5-star property

Omni Chicago Hotel

9.2/10 Wonderful! (1,574 reviews)

Nov 28 - Nov 30

2 night stay

Toronto (YYZ) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to Toronto (YYZ)

Delta • Coach
Price was $501, price is now $417 per person
$417
per person
found 1 day ago
Much better stay than last time - which was met with rude and lazy staff. (Walked into new room with hair in sink, no toilet paper. Called for 4 hours only to be told to to use the public restroom. Went to desk and spoke directly to "manager" insisting that he provide it. Told me "When we get to it we get to it." I was LIVID, whereupon he promised a partial refund in 2-3 days. Received nothing.) Why did I stay here again? Last minute reservation and ideal to location to hospital I needed to go.) If Omni is like this normally, I'd stay again.

Reviewed on Aug 28, 2025

Sofitel Chicago Magnificent Mile
4.5-star property

Sofitel Chicago Magnificent Mile

9.4/10 Exceptional! (2,126 reviews)

Nov 28 - Nov 30

2 night stay

Toronto (YYZ) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to Toronto (YYZ)

Delta • Coach
Price was $466, price is now $399 per person
$399
per person
found 1 day ago
Hotel was amazing. Surrounding area was good too.

Reviewed on Oct 1, 2025

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More About Flying To Chicago from Kitchener

Route Information for Flights from Kitchener to Chicago

Origin Airport IATA Code
YTO
Destination Airport IATA Code
CHI
Distance
436 mi
Direct Flight Airlines
American Airlines, Qatar Airways, JAL, Air Canada, EgyptAir, Copa Airlines, Air New Zealand, United Airlines, Alaska Airlines, Porter Airlines, Qantas, Royal Jordanian, Iberia, ANA, British Airways
Earliest Flight Arrival
11:25AM UTC
Latest Flight Arrival
2:07AM UTC

Kitchener to Chicago

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Frequently asked questions

Are there non-stop flights from Kitchener to Chicago?
There are 3 airlines that offer nonstop services from Toronton Pearson to ORD, so get ready to click that beautiful "book" button. One of these top carriers will have the flight you're looking for:

  • Air Canada
  • United Airlines
  • American Airlines

What is the shortest flight from Kitchener to Chicago?
It can be as a short and sweet as 1 hour and 50 minutes. If you're of the opinion that your vacation hours should be spent 'vacationing' rather than flying, you'll enjoy the trip from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (ORD-O'Hare Intl.).
What airlines fly from Kitchener to Chicago most frequently?
The airlines that offer the most frequent flights between Pearson Intl. Airport (YYZ) and ORD include Air Canada (AC). This popular option offers 152 flights on the route every month. United Airlines (UA) will also fly you to your destination in comfort and style. Offering 91 flights every month between Kitchener and Chicago, it's another popular airline to look into.
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.