Cheap Flights to Kendall County from $28

View $28 flight on Sat, May 2, 2026Opens in a new window

Popular airlines to Kendall County

  • Delta

  • Frontier Airlines

  • American Airlines

  • United

  • Spirit Airlines

  • Alaska Airlines

  • Southwest Airlines

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How much is the cheapest flight to Kendall County?

Prices were available within the past 7 days and start at $28 for one-way flights and $56 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, May 2 - Tue, May 5
IAH
Houston
ORD
Chicago
$56 Roundtrip, just found
$56
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 2 from Houston to Chicago, returning Tue, May 5, priced at $56 just found
Frontier Airlines
Sat, May 2 - Sun, May 3
EWR
New York
MDW
Chicago
$56 Roundtrip, just found
$56
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 2 from New York to Chicago, returning Sun, May 3, priced at $56 just found
Frontier Airlines
Sat, May 2 - Tue, May 5
IAH
Houston
ORD
Chicago
$61 Roundtrip, just found
$61
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 2 from Houston to Chicago, returning Tue, May 5, priced at $61 just found
Frontier Airlines
Sat, May 2 - Mon, May 4
IAH
Houston
ORD
Chicago
$62 Roundtrip, just found
$62
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 2 from Houston to Chicago, returning Mon, May 4, priced at $62 just found
Frontier Airlines
Tue, Apr 28 - Sat, May 2
ATL
Atlanta
MDW
Chicago
$68 Roundtrip, just found
$68
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Apr 28 from Atlanta to Chicago, returning Sat, May 2, priced at $68 just found
Frontier Airlines
Sat, Apr 25 - Sun, May 3
EWR
New York
MDW
Chicago
$71 Roundtrip, found 19 hours ago
$71
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sat, Apr 25 from New York to Chicago, returning Sun, May 3, priced at $71 found 19 hours ago
Spirit Airlines
Thu, Apr 30 - Fri, May 1
ATL
Atlanta
ORD
Chicago
$73 Roundtrip, just found
$73
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Apr 30 from Atlanta to Chicago, returning Fri, May 1, priced at $73 just found
American Airlines
Wed, Jun 3 - Tue, Jun 9
IAH
Houston
ORD
Chicago
$169 Roundtrip, found 1 hour ago
$169
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Jun 3 from Houston to Chicago, returning Tue, Jun 9, priced at $169 found 1 hour ago
United
Wed, Jun 17 - Tue, Jun 23
IAH
Houston
ORD
Chicago
$169 Roundtrip, found 2 hours ago
$169
Roundtrip
found 2 hours ago
Select United flight, departing Wed, Jun 17 from Houston to Chicago, returning Tue, Jun 23, priced at $169 found 2 hours ago
Southwest Airlines
Sat, May 2 - Tue, May 12
LGA
New York
MDW
Chicago
$176 Roundtrip, found 16 hours ago
$176
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Sat, May 2 from New York to Chicago, returning Tue, May 12, priced at $176 found 16 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. Flights from $206
ORD
O'Hare Intl.
Flights from $206
Select flight to Midway Intl. MDW. Cheapest option available. Flights from $201
MDW
Midway Intl.
Cheapest
Flights from $201

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
Sat, May 2 - Sun, May 3
EWR
New York
MDW
Chicago
$56 Roundtrip, just found
$56
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 2 from New York to Chicago, returning Sun, May 3, priced at $56 just found

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, $56 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 $56 and $176 in the last seven days. For one-way journeys from Houston (IAH), the lowest price during this time was just $28.
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 $56 and $176. 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.

Travel information

*Flight schedules are subject to change.

*Available to One Key members.

 

*Flight schedules are subject to change.

*Available to One Key members.

 

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