$89 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.

Sat, Aug 2 - Sun, Aug 17
YKF
Region of Waterloo Intl.
ORD
O'Hare Intl.
$294 Roundtrip, found 6 days ago
$294
Roundtrip
found 6 days ago
Select Air Canada flight, departing Sat, Aug 2 from Region of Waterloo Intl. to O'Hare Intl., returning Sun, Aug 17, priced at $294 found 6 days ago
Sat, Aug 2 - Sun, Aug 17
YHM
John C. Munro Hamilton Intl.
ORD
O'Hare Intl.
$294 Roundtrip, found 6 days ago
$294
Roundtrip
found 6 days ago
Select Air Canada flight, departing Sat, Aug 2 from John C. Munro Hamilton Intl. to O'Hare Intl., returning Sun, Aug 17, priced at $294 found 6 days ago
Sun, Aug 3 - Wed, Aug 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 Sun, Aug 3 from Billy Bishop Toronto City to Midway Intl., returning Wed, Aug 6, priced at $346 found 5 days ago
Sat, Aug 2 - Tue, Aug 5
YYZ
Pearson Intl.
MDW
Midway Intl.
$434 Roundtrip, found 6 days ago
$434
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Aug 2 from Pearson Intl. to Midway Intl., returning Tue, Aug 5, priced at $434 found 6 days ago

Airfares from $89 One Way, $135 Round Trip from Kitchener to Chicago

Prices starting at $135 for return flights and $89 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.

Mon, Oct 20 - Thu, Oct 23
YTZ
Toronto
MDW
Chicago
$135 Roundtrip, just found
$135
Roundtrip
just found
Select Porter Airlines flight, departing Mon, Oct 20 from Toronto to Chicago, returning Thu, Oct 23, priced at $135 just found
Fri, Oct 31 - Thu, Nov 6
YYZ
Toronto
ORD
Chicago
$142 Roundtrip, found 3 days ago
$142
Roundtrip
found 3 days ago
Select United flight, departing Fri, Oct 31 from Toronto to Chicago, returning Thu, Nov 6, priced at $142 found 3 days ago
Wed, Nov 5 - Sat, Nov 22
YYZ
Toronto
ORD
Chicago
$142 Roundtrip, found 3 days ago
$142
Roundtrip
found 3 days ago
Select Air Canada flight, departing Wed, Nov 5 from Toronto to Chicago, returning Sat, Nov 22, priced at $142 found 3 days ago
Tue, Dec 2 - Mon, Dec 15
YYZ
Toronto
ORD
Chicago
$161 Roundtrip, found 3 days ago
$161
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Dec 2 from Toronto to Chicago, returning Mon, Dec 15, priced at $161 found 3 days ago
Mon, Sep 8 - Wed, Sep 10
YTZ
Toronto
MDW
Chicago
$192 Roundtrip, found 6 hours ago
$192
Roundtrip
found 6 hours ago
Select Air Transat flight, departing Mon, Sep 8 from Toronto to Chicago, returning Wed, Sep 10, priced at $192 found 6 hours ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0-star property

Hilton Garden Inn Chicago Downtown/Magnificent Mile

8.4/10 Very Good! (3,506 reviews)

Aug 28 - Aug 31

3 night stay

Toronto (YTO) to Chicago (ORD)

Porter Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 3 hours ago
Great place will stay again

Reviewed on Jul 27, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,635 reviews)

Aug 28 - Aug 31

3 night stay

Toronto (YTO) to Chicago (ORD)

Porter Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 3 hours ago
This is the nicest hotel that I have ever stayed at. Everything was perfect!

Reviewed on Jun 16, 2025

citizenM Chicago Downtown
4.0-star property

citizenM Chicago Downtown

9.4/10 Exceptional! (3,315 reviews)

Aug 28 - Aug 31

3 night stay

Toronto (YTO) to Chicago (ORD)

Porter Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 3 hours ago
Nice, staff, good location

Reviewed on Jun 22, 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, Qantas, Royal Jordanian, Iberia, ANA, British Airways
Earliest Flight Arrival
11:25AM UTC
Latest Flight Arrival
2:05AM 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.

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.