Cheap Flights to Kendall County from $29

View $29 flight on Sat, Feb 21, 2026Opens in a new window

Popular airlines to Kendall County

  • Delta

    Delta

  • Frontier Airlines

    Frontier Airlines

  • American Airlines

    American Airlines

  • United

    United

  • Southwest Airlines

    Southwest Airlines

  • Spirit Airlines

    Spirit Airlines

  • Alaska Airlines

    Alaska Airlines

  • notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
  • deals illustration

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • trophy illustration

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

How much is the cheapest flight to Kendall County?

Prices were available within the past 7 days and start at $29 for one-way flights and $54 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Tue, Jan 13 - Thu, Jan 15
EWR
New York
MDW
Chicago
$54 Roundtrip, found 4 hours ago
$54
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Tue, Jan 13 from New York to Chicago, returning Thu, Jan 15, priced at $54 found 4 hours ago
Frontier Airlines
Sat, Jan 10 - Sat, Jan 17
JFK
New York
ORD
Chicago
$58 Roundtrip, just found
$58
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Jan 10 from New York to Chicago, returning Sat, Jan 17, priced at $58 just found
Frontier Airlines
Sat, Feb 21 - Sat, Feb 28
DFW
Dallas
MDW
Chicago
$58 Roundtrip, just found
$58
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Feb 21 from Dallas to Chicago, returning Sat, Feb 28, priced at $58 just found
Frontier Airlines
Sat, Feb 21 - Sat, Feb 28
DFW
Dallas
ORD
Chicago
$58 Roundtrip, just found
$58
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Feb 21 from Dallas to Chicago, returning Sat, Feb 28, priced at $58 just found
Frontier Airlines
Wed, Jan 14 - Sat, Jan 17
ATL
Atlanta
ORD
Chicago
$58 Roundtrip, just found
$58
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Jan 14 from Atlanta to Chicago, returning Sat, Jan 17, priced at $58 just found
Frontier Airlines
Thu, Jan 15 - Sun, Jan 18
EWR
New York
MDW
Chicago
$61 Roundtrip, found 3 hours ago
$61
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Jan 15 from New York to Chicago, returning Sun, Jan 18, priced at $61 found 3 hours ago
Spirit Airlines
Tue, Jan 20 - Wed, Jan 21
LGA
New York
ORD
Chicago
$68 Roundtrip, just found
$68
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Jan 20 from New York to Chicago, returning Wed, Jan 21, priced at $68 just found
Southwest Airlines
Mon, Feb 9 - Wed, Feb 11
LGA
New York
MDW
Chicago
$125 Roundtrip, found 6 days ago
$125
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Mon, Feb 9 from New York to Chicago, returning Wed, Feb 11, priced at $125 found 6 days ago
Contour Airlines
Wed, Jan 7 - Sun, Jan 11
DFW
Dallas
ORD
Chicago
$189 Roundtrip, just found
$189
Roundtrip
just found
Select Contour Airlines flight, departing Wed, Jan 7 from Dallas to Chicago, returning Sun, Jan 11, priced at $189 just found
Alaska Airlines
Sat, Feb 14 - Wed, Feb 18
LAX
Los Angeles
ORD
Chicago
$240 Roundtrip, found 2 hours ago
$240
Roundtrip
found 2 hours ago
Select Alaska Airlines flight, departing Sat, Feb 14 from Los Angeles to Chicago, returning Wed, Feb 18, priced at $240 found 2 hours ago

Airports in Kendall County

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Flights from $189
ORD
O'Hare Intl.
Cheapest
Flights from $189
Select flight to Midway Intl. MDW. Flights from $284
MDW
Midway Intl.
Flights from $284

Enjoy extra legroom, flight flexibility, and a seamless travel experience.

Kendall County Flights Information

Airlines serving
Frontier Airlines, Spirit Airlines, American Airlines, Delta, United, Southwest Airlines, Contour Airlines, Alaska Airlines
Roundtrip price
from $54

Frequently asked questions

How do I find cheap flights to Kendall County that have flexible change policies?
We understand that travel arrangements can change in a flash, so choosing a flexible airfare with Expedia is always a smart move. Just tick the "No change fee" box underneath the "Flexible change policies" filter. Your well-priced and flexible flight to Kendall County is just a few clicks away.
Which airlines fly to Kendall County?
When you're ready to lock in your ticket to or near Kendall County, these airlines are waiting to welcome you aboard:

  • United Airlines - 12,954 flights to or near Kendall County each month, including 12,950 flights to O'Hare Intl. Airport (ORD) per month.
  • American Airlines - 8,855 flights to or near Kendall County each month, including 8,855 flights to O'Hare Intl. Airport (ORD) per month.
  • Southwest Airlines - 5,997 flights to or near Kendall County each month, including 5,334 flights to Midway Intl. Airport (MDW) per month.

How can I find cheap tickets to Kendall County?
In the last seven days, $54 was the lowest price for a flight to Kendall County. For an even better fare, book well in advance and be flexible with your travel dates. Search for your flight to Kendall County, then check out prices for nearby days by clicking on the "flexible dates" link above.
How much is a flight to Kendall County?
You could have locked in a round-trip airfare to Kendall County from anywhere between $54 and $240 in the last seven days. For one-way journeys from Dallas (DFW), the lowest price during this time was just $29.
What are the most popular airports to fly into in Kendall County?
Adventure awaits the moment you cruise into one of these well-known Kendall County airports:

  • O'Hare Intl. Airport (ORD) - 25,318 flights per month.
  • Midway Intl. Airport (MDW) - 5,962 flights per month.

When is the cheapest time to fly to Kendall County?
Fly out on a Tuesday to boost your odds of bagging the cheapest flight to Kendall County. Mondays are usually the next most affordable day to depart. Saturday is generally the costliest day to fly anywhere.
How much is a plane ticket to Kendall County?
In the last seven days, airfares ranged between $54 and $240. Check out our terrific deals to Kendall County, pick your favorite and get ready for your next fun vacation!
What months are the cheapest to book a flight to Kendall County?
To score a great deal to Kendall County, book during the month of February when ticket prices are at their cheapest. When do tickets cost the most? In the U.S, it's December.
How long is a flight to Kendall County?
It depends on a couple of different things, such as where you take off from and whether you're on a direct or multi-stop flight. Listed below are some of the busiest domestic routes to Kendall County and their average flight durations:

  • New York, NY (LGA-LaGuardia) to O'Hare Intl. Airport (ORD) - 2 hours and 39 minutes
  • Los Angeles, CA (LAX-Los Angeles Intl.) to O'Hare Intl. Airport (ORD) - 4 hours and 4 minutes
  • Dallas, TX (DFW-Dallas-Fort Worth Intl.) to O'Hare Intl. Airport (ORD) - 2 hours and 31 minutes

What is the best time to go to Kendall County?
A popular time to check out Kendall County, along with the exciting city of Oswego, is over the lively months of April, June and August. Summer in this part of the world starts June 20, and you can expect temperatures of between 65ºF and 80ºF if you go then. This warmer weather is perfect for wandering around this city's attractions.

Trending flights to Kendall County

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Tue, Jan 13 - Thu, Jan 15
EWR
New York
MDW
Chicago
$54 Roundtrip, found 4 hours ago
$54
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Tue, Jan 13 from New York to Chicago, returning Thu, Jan 15, priced at $54 found 4 hours ago
*Available to One Key members.