Flights To Kendall County - Cheap Flights Starting at CA $191

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Yorkville

Flights
Yorkville

How Much Does it Cost To Fly To Kendall County?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, Sep 12 - Mon, Sep 21
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $312 Roundtrip, found 5 days ago
CA $312
Roundtrip
found 5 days ago
Select Porter Airlines flight, departing Sat, Sep 12 from Billy Bishop Toronto City to Midway Intl., returning Mon, Sep 21, priced at CA $312 found 5 days ago
Fri, Sep 18 - Mon, Sep 21
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $334 Roundtrip, found 3 hours ago
CA $334
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Fri, Sep 18 from Pearson Intl. to O'Hare Intl., returning Mon, Sep 21, priced at CA $334 found 3 hours ago
Fri, Nov 6 - Sun, Nov 8
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $341 Roundtrip, found 1 day ago
CA $341
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Fri, Nov 6 from Billy Bishop Toronto City to O'Hare Intl., returning Sun, Nov 8, priced at CA $341 found 1 day ago
Tue, Sep 8 - Mon, Sep 14
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $342 Roundtrip, found 21 hours ago
CA $342
Roundtrip
found 21 hours ago
Select Delta flight, departing Tue, Sep 8 from Pearson Intl. to Midway Intl., returning Mon, Sep 14, priced at CA $342 found 21 hours ago
Sat, Sep 19 - Sat, Sep 26
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $353 Roundtrip, just found
CA $353
Roundtrip
just found
Select Air Transat flight, departing Sat, Sep 19 from Billy Bishop Toronto City to Midway Intl., returning Sat, Sep 26, priced at CA $353 just found
Fri, Aug 28 - Tue, Sep 1
YYC
Calgary Intl.
ORD
O'Hare Intl.
CA $360 Roundtrip, found 3 days ago
CA $360
Roundtrip
found 3 days ago
Select WestJet flight, departing Fri, Aug 28 from Calgary Intl. to O'Hare Intl., returning Tue, Sep 1, priced at CA $360 found 3 days ago
Tue, Nov 17 - Wed, Nov 25
YUL
Pierre Elliott Trudeau Intl.
MDW
Midway Intl.
CA $389 Roundtrip, found 2 days ago
CA $389
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Nov 17 from Pierre Elliott Trudeau Intl. to Midway Intl., returning Wed, Nov 25, priced at CA $389 found 2 days ago
Sat, Sep 5 - Sat, Sep 12
YUL
Pierre Elliott Trudeau Intl.
ORD
O'Hare Intl.
CA $389 Roundtrip, found 1 day ago
CA $389
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 5 from Pierre Elliott Trudeau Intl. to O'Hare Intl., returning Sat, Sep 12, priced at CA $389 found 1 day ago
OriginDestinationTravel datesFlights from*
LAXChicagoSeptember 8 to September 11CA $455
HKGChicagoOctober 19 to December 3CA $1,322
PEKChicagoSeptember 3 to September 16CA $1,684
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
LAXChicagoJuly 24 to July 26CA $880
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

Sep 23 - Sep 26

3 night stay

Toronto (YTO) to Chicago (ORD)

Porter Airlines • Roundtrip • Coach
Price was CA $1,240, price is now CA $831 per person
CA $831
per person
found 1 day ago
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Sep 23 - Sep 26

3 night stay

Toronto (YTO) to Chicago (ORD)

Porter Airlines • Roundtrip • Coach
Price was CA $1,525, price is now CA $1,029 per person
CA $1,029
per person
found 1 day ago
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sep 23 - Sep 26

3 night stay

Toronto (YTO) to Chicago (ORD)

Porter Airlines • Roundtrip • Coach
Price was CA $2,040, price is now CA $1,404 per person
CA $1,404
per person
found 1 day ago
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Travelers ❤️ These Kendall County 🏨

DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
3003 Corporate West Dr Naperville IL
Book a stay at this business-friendly hotel in Naperville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Naperville Yard Indoor Sports Complex and Sea Lion Aquatic Park are located nearby.
7.8/10 Good! (1,368 reviews)
"Very enjoyable stay...loved the shower facility"

Reviewed on Jul 20, 2026

Opens in a new windowDoubleTree by Hilton Lisle Naperville
Chicago Club Inn & Suites

Chicago Club Inn & Suites

3 out of 5
630 Pasquinelli Dr Westmont IL
Book a stay at this business-friendly hotel in Westmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the clean rooms in our reviews. Popular attractions Oakbrook Center Mall and Ty Warner Park are located nearby.
7.2/10 Good! (1,660 reviews)
"Was are thin if you know what I mean!!!!! They are working on the place and it needs it had to change rooms bc air froze up and refrigerator"

Reviewed on Jul 20, 2026

Opens in a new windowChicago Club Inn & Suites
Red Roof Inn PLUS+ Chicago - Willowbrook

Red Roof Inn PLUS+ Chicago - Willowbrook

2.5 out of 5
7535 Kingery Highway Willowbrook IL
Stay at this hotel in Willowbrook. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Willowbrook Community Park and Burr Ridge Village Center are located nearby.
6.4/10 (1,203 reviews)
"Smelly Rooms. Very poorly maintained."

Reviewed on Jul 21, 2026

Opens in a new windowRed Roof Inn PLUS+ Chicago - Willowbrook
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Embassy Suites by Hilton Chicago Lombard Oak Brook

Embassy Suites by Hilton Chicago Lombard Oak Brook

3.5 out of 5
707 E Butterfield Road Lombard IL
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Oakbrook Center Mall and Yorktown Shopping Center are located nearby.
8.2/10 Very good! (1,712 reviews)
"I ordered two rooms and they were clean and big and me and my family really enjoyed our stay!!! And will be going back and the breakfast was good."

Reviewed on Jul 20, 2026

Opens in a new windowEmbassy Suites by Hilton Chicago Lombard Oak Brook
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is the cheapest flight to Kendall County?
A roundtrip flight to Kendall County cost as little as CA $312 in the last seven days. When you've narrowed down your travel dates, we'll help you land a good deal. This price was available on Travelocity for flights to Kendall County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Kendall County?
When organizing your Kendall County escape, you can pick from 15 airlines. Make United Airlines your number one choice for flights to Oswego. It offers roughly 15,032 flights every month to this vibrant city.
What is the cheapest month to fly to Kendall County?
Spend more of your money on epic experiences and less on your airfare by zipping off to Kendall County in September. This is the cheapest month to jet out to this destination based on Travelocity's direct return flight demand between January and December last year. Take a peek at our selection of flights and get away without draining your bank account.
How can I check my flight status to Kendall County?
Head to Travelocity's handy portal, Trips. You'll find everything related to your flight to Kendall County here, including important details about any gate changes, flight delays and more. Click on Trips at the top right of the Travelocity homepage. Just create your free acount and get the answers you need. Or, access your itinerary while you're on the move and get real-time notifications through the Travelocity app. You'll find all your itineraries in one convenient place, so you can quickly share details with any members of your family flying with you.
How do I find the best deals on flights to Kendall County?
Being flexible with your travel dates is one of the best ways to score an amazing deal. Travelocity makes it super simple to find your ideal fare through the "Flexible dates" function. Search for your flight to Kendall County, then compare the cheapest prices for surrounding days by clicking the "Flexible dates" box at the top of the page. Booking earlier and avoiding peak periods are other ways to save some cash. In the last seven days, the lowest price for a return flight to Kendall County was CA $312. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Kendall County with Travelocity?
If you're seeking cheap flights to Kendall County, you'll find some top deals with Travelocity. From cheap family flights on low-cost carriers to flexible tickets, we can help with your journey. Experience a stress-free trip with our 24/7 customer assistance, Price Match Guarantee and free cancellation policies with most hotels. Start planning your travel agenda and prepare to jump on a plane to this fabulous destination.
What are the most popular flight routes to Kendall County?
If you're planning to catch a flight to Kendall County, here are some of the most popular routes to think about:

  • Denver, CO (DEN-Denver Intl.) to O'Hare Intl. Airport (ORD) - 4,203 flights a month.
  • Minneapolis, MN (MSP-Minneapolis - St. Paul Intl.) to O'Hare Intl. Airport (ORD) - 4,155 flights a month.
  • New York, NY (LGA-LaGuardia) to O'Hare Intl. Airport (ORD) - 4,138 flights a month.

How much is a flight to Kendall County on average?
Fares for roundtrip flights to Kendall County were priced between CA $312 and CA $1,684 in the last seven days. The moment you find an awesome deal, lock it in and prepare to jet off on the vacation of your dreams with Travelocity. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.