Flights To Kendall County - Cheap Flights Starting at CA $185

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Fox River, Silver Springs State Park, Yorkville, Illinois USA

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.

Thu, Jun 18 - Mon, Jun 22
YYZ
Pearson Intl.
MDW
Midway Intl.
CA $329 Roundtrip, found 1 hour ago
CA $329
Roundtrip
found 1 hour ago
Select Delta flight, departing Thu, Jun 18 from Pearson Intl. to Midway Intl., returning Mon, Jun 22, priced at CA $329 found 1 hour ago
Tue, Sep 8 - Tue, Sep 8
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $338 Roundtrip, found 21 hours ago
CA $338
Roundtrip
found 21 hours ago
Select Porter Airlines flight, departing Tue, Sep 8 from Billy Bishop Toronto City to O'Hare Intl., returning Tue, Sep 8, priced at CA $338 found 21 hours ago
Mon, Jun 1 - Thu, Jun 4
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $342 Roundtrip, found 6 days ago
CA $342
Roundtrip
found 6 days ago
Select Air Canada flight, departing Mon, Jun 1 from Billy Bishop Toronto City to O'Hare Intl., returning Thu, Jun 4, priced at CA $342 found 6 days ago
Sun, Jun 14 - Fri, Jun 19
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
CA $343 Roundtrip, just found
CA $343
Roundtrip
just found
Select Porter Airlines flight, departing Sun, Jun 14 from Billy Bishop Toronto City to Midway Intl., returning Fri, Jun 19, priced at CA $343 just found
Wed, Jun 17 - Sun, Jun 21
YYZ
Pearson Intl.
ORD
O'Hare Intl.
CA $346 Roundtrip, found 10 hours ago
CA $346
Roundtrip
found 10 hours ago
Select United flight, departing Wed, Jun 17 from Pearson Intl. to O'Hare Intl., returning Sun, Jun 21, priced at CA $346 found 10 hours ago
Fri, Aug 14 - Tue, Aug 25
YYC
Calgary Intl.
ORD
O'Hare Intl.
CA $380 Roundtrip, found 4 days ago
CA $380
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Aug 14 from Calgary Intl. to O'Hare Intl., returning Tue, Aug 25, priced at CA $380 found 4 days ago
Fri, Nov 13 - Sun, Nov 15
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
CA $380 Roundtrip, found 1 day ago
CA $380
Roundtrip
found 1 day ago
Select Air Transat flight, departing Fri, Nov 13 from Billy Bishop Toronto City to O'Hare Intl., returning Sun, Nov 15, priced at CA $380 found 1 day ago
Tue, Apr 6 - Mon, Apr 12
YYC
Calgary Intl.
ORD
O'Hare Intl.
CA $383 Roundtrip, found 3 days ago
CA $383
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Apr 6 from Calgary Intl. to O'Hare Intl., returning Mon, Apr 12, priced at CA $383 found 3 days ago
OriginDestinationTravel datesFlights from*
LAXChicagoAugust 20 to August 25CA $447
LAXChicagoAugust 14 to August 16CA $654
FCOChicagoAugust 3 to November 4CA $1,238
HKGChicagoJune 14 to September 4CA $1,507
PEKChicagoJune 18 to June 23CA $1,632
PVGChicagoJune 22 to July 8CA $1,862
XIYChicagoJuly 25 to August 15CA $2,555
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
LAXChicagoMay 29 to June 21CA $809
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

Jul 21 - Jul 24

3 night stay

Toronto (YTO) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Price was CA $1,507, price is now CA $1,029 per person
CA $1,029
per person
found 1 day ago
Pendry Chicago
4.5-star property

Pendry Chicago

Jul 28 - Jul 31

3 night stay

Toronto (YTO) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Price was CA $1,707, price is now CA $1,146 per person
CA $1,146
per person
found 1 day ago
The Talbott, Autograph Collection
4.5-star property

The Talbott, Autograph Collection

Jun 27 - Jul 1

4 night stay

Toronto (YTO) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Price was CA $1,574, price is now CA $1,063 per person
CA $1,063
per person
found 21 hours ago
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Travelers ❤️ These Kendall County 🏨

Best Western Oswego Hotel

Best Western Oswego Hotel

2.5 out of 5
2055 Wiesbrook Dr Oswego IL
Book a stay at this business-friendly hotel in Oswego. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Aurora Skate Center and SciTech Hands on Museum are located nearby.
8.8/10 Excellent! (909 reviews)
"Would definitely stay here again."

Reviewed on May 20, 2026

Opens in a new windowBest Western Oswego Hotel
SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

2.5 out of 5
222 E 22nd Street Lombard IL
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Yorktown Shopping Center and Lilacia Park are located nearby.
9/10 Wonderful! (2,753 reviews)
"Checking in was easy and room was semi clean. The blanket in the closet was covered in food and super dirty. Saw a sign that said water maintenance would be over at 12pm. Checked in at 3pm, water still didn't work until 4pm. It was very inconvenient."

Reviewed on May 22, 2026

Opens in a new windowSureStay Plus Hotel by Best Western Chicago Lombard
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 Ty Warner Park and Mayslake Peabody Mansion are located nearby.
7.2/10 Good! (1,556 reviews)
"Clean room"

Reviewed on May 22, 2026

Opens in a new windowChicago Club Inn & Suites
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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 Yorktown Shopping Center and Mayslake Peabody Mansion are located nearby.
8.2/10 Very Good! (1,574 reviews)
"Omelettes were delicious"

Reviewed on May 18, 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 $329 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 June. 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 $329. 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 $329 and CA $2,555 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.