$96 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, Jul 5 - Wed, Jul 9
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
$422 Roundtrip, found 14 hours ago
$422
Roundtrip
found 14 hours ago
Select Porter Airlines flight, departing Sat, Jul 5 from Billy Bishop Toronto City to Midway Intl., returning Wed, Jul 9, priced at $422 found 14 hours ago
Sat, Jul 5 - Tue, Jul 15
YYZ
Pearson Intl.
ORD
O'Hare Intl.
$438 Roundtrip, found 11 hours ago
$438
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Sat, Jul 5 from Pearson Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $438 found 11 hours ago
Sat, Jul 5 - Wed, Jul 9
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
$473 Roundtrip, found 14 hours ago
$473
Roundtrip
found 14 hours ago
Select Air Canada flight, departing Sat, Jul 5 from Billy Bishop Toronto City to O'Hare Intl., returning Wed, Jul 9, priced at $473 found 14 hours ago
Sun, Jul 6 - Fri, Jul 11
YHM
John C. Munro Hamilton Intl.
ORD
O'Hare Intl.
$654 Roundtrip, found 16 hours ago
$654
Roundtrip
found 16 hours ago
Select Air Canada flight, departing Sun, Jul 6 from John C. Munro Hamilton Intl. to O'Hare Intl., returning Fri, Jul 11, priced at $654 found 16 hours ago

Airfares from $96 One Way, $148 Round Trip from Kitchener to Chicago

Prices starting at $148 for return flights and $96 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.

Thu, Nov 6 - Wed, Nov 12
YTZ
Toronto
MDW
Chicago
$148 Roundtrip, just found
$148
Roundtrip
just found
Select Porter Airlines flight, departing Thu, Nov 6 from Toronto to Chicago, returning Wed, Nov 12, priced at $148 just found
Fri, Sep 12 - Mon, Sep 15
YYZ
Toronto
ORD
Chicago
$155 Roundtrip, found 2 hours ago
$155
Roundtrip
found 2 hours ago
Select United flight, departing Fri, Sep 12 from Toronto to Chicago, returning Mon, Sep 15, priced at $155 found 2 hours ago
Fri, Sep 12 - Mon, Sep 15
YYZ
Toronto
ORD
Chicago
$155 Roundtrip, found 2 hours ago
$155
Roundtrip
found 2 hours ago
Select Air Canada flight, departing Fri, Sep 12 from Toronto to Chicago, returning Mon, Sep 15, priced at $155 found 2 hours ago
Thu, Aug 21 - Sun, Aug 24
YKF
Kitchener
ORD
Chicago
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Select Air Canada flight, departing Thu, Aug 21 from Kitchener to Chicago, returning Sun, Aug 24, priced at $163 found 1 day ago
Thu, Aug 21 - Sun, Aug 24
YHM
Hamilton
ORD
Chicago
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Select Air Canada flight, departing Thu, Aug 21 from Hamilton to Chicago, returning Sun, Aug 24, priced at $163 found 1 day ago

More About Flying To Chicago from Kitchener

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.