$89 Cheap flights to Caldwell County

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Cheap flights to Caldwell County from $89 One Way, $175 Round Trip

$175 return flights and $89 one-way flights to Caldwell County 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, Aug 27 - Thu, Aug 27
ORD
Chicago
MWA
Marion
$175 Roundtrip, found 3 days ago
$175
Roundtrip
found 3 days ago
Select Contour Airlines flight, departing Thu, Aug 27 from Chicago to Marion, returning Thu, Aug 27, priced at $175 found 3 days ago
Fri, Oct 9 - Sun, Oct 11
ORD
Chicago
OWB
Owensboro
$178 Roundtrip, found 16 hours ago
$178
Roundtrip
found 16 hours ago
Select Contour Airlines flight, departing Fri, Oct 9 from Chicago to Owensboro, returning Sun, Oct 11, priced at $178 found 16 hours ago
Sat, Aug 22 - Mon, Aug 24
ORD
Chicago
OWB
Owensboro
$181 Roundtrip, found 20 hours ago
$181
Roundtrip
found 20 hours ago
Select Contour Airlines flight, departing Sat, Aug 22 from Chicago to Owensboro, returning Mon, Aug 24, priced at $181 found 20 hours ago
Thu, Oct 8 - Sun, Oct 11
CLT
Charlotte
OWB
Owensboro
$188 Roundtrip, found 1 day ago
$188
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Thu, Oct 8 from Charlotte to Owensboro, returning Sun, Oct 11, priced at $188 found 1 day ago
Tue, Sep 1 - Wed, Sep 2
ORD
Chicago
OWB
Owensboro
$232 Roundtrip, found 4 days ago
$232
Roundtrip
found 4 days ago
Select Contour Airlines flight, departing Tue, Sep 1 from Chicago to Owensboro, returning Wed, Sep 2, priced at $232 found 4 days ago
Tue, Sep 8 - Sun, Sep 20
CHS
Charleston
PAH
Paducah
$304 Roundtrip, found 4 days ago
$304
Roundtrip
found 4 days ago
Select United flight, departing Tue, Sep 8 from Charleston to Paducah, returning Sun, Sep 20, priced at $304 found 4 days ago
Thu, Aug 27 - Mon, Aug 31
BNA
Nashville
MWA
Marion
$363 Roundtrip, found 20 hours ago
$363
Roundtrip
found 20 hours ago
Select Contour Airlines flight, departing Thu, Aug 27 from Nashville to Marion, returning Mon, Aug 31, priced at $363 found 20 hours ago
Thu, Nov 19 - Sun, Nov 22
CLT
Charlotte
PAH
Paducah
$365 Roundtrip, found 1 day ago
$365
Roundtrip
found 1 day ago
Select United flight, departing Thu, Nov 19 from Charlotte to Paducah, returning Sun, Nov 22, priced at $365 found 1 day ago
Sun, Aug 23 - Thu, Aug 27
FLL
Fort Lauderdale
OWB
Owensboro
$437 Roundtrip, found 2 days ago
$437
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sun, Aug 23 from Fort Lauderdale to Owensboro, returning Thu, Aug 27, priced at $437 found 2 days ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
ORDOwensboroAugust 15 to August 27$267
CLTOwensboroAugust 16 to August 19$272
ATLEvansvilleAugust 16 to August 17$706
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Caldwell County Accommodation Deals

Kentucky Dam Village State Resort Park

Kentucky Dam Village State Resort Park

3 out of 5
166 upper village Dr Gilbertsville KY
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $84 total per night from Aug 11 to Aug 12
$84 total
Aug 11 - Aug 12
Total with taxes and fees
Book a stay at this beach hotel in Gilbertsville. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff ...
9/10 Wonderful! (1,161 reviews)
"We had a beautiful view and the rooms were very nice and clean. The pool was out of order unfortunately. It would be nice if there was a microwave and mini fridge in the rooms. But overall it was a great experience and I will definitely be staying again!"

Reviewed on Aug 9, 2026

Opens in a new windowKentucky Dam Village State Resort Park
Days Inn by Wyndham Madisonville

Days Inn by Wyndham Madisonville

2 out of 5
1900 Lantaff Blvd Madisonville KY
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $78 total per night from Sep 6 to Sep 7
$78 total
Sep 6 - Sep 7
Total with taxes and fees
Stay at this hotel in Madisonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Opens in a new windowDays Inn by Wyndham Madisonville
Baymont by Wyndham Madisonville

Baymont by Wyndham Madisonville

2.5 out of 5
1891 Lantaff Blvd Madisonville KY
$98 nightly
The price is $109 total per night from Aug 23 to Aug 24
$109 total
Aug 23 - Aug 24
Total with taxes and fees
Stay at this hotel in Madisonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (369 reviews)
"Nice"

Reviewed on Aug 5, 2026

Opens in a new windowBaymont by Wyndham Madisonville
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Hotel Barkley

Hotel Barkley

2 out of 5
139 Days Inn Drive Kuttawa KY
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $84 total per night from Sep 7 to Sep 8
$84 total
Sep 7 - Sep 8
Total with taxes and fees
Stay at this motel in Kuttawa. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Opens in a new windowHotel Barkley
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.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Caldwell County

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Register for Orbitz email updates and our cruise experts will notify you of bargain tickets on cruises as they’re posted. Install our free mobile apps on your iPad, iPhone or Android for easy booking and mobile-only savings on flights to Caldwell County. Visit www.Orbitz.com to learn more about these amazing benefits and our 110% Best Price Guarantee.

First-Timers

Are you and your family cruise newbies? Orbitz offers Cruising 101 and Cruise FAQ to answer any questions you may have. Book your cruise and air travel with Orbitz On the Go for greater savings on Caldwell County flights.

Ports and Play

Be sure to check our cruise page for free shore excursions, onboard spending, balcony upgrades and other perks. Orbitz offers last-minute, luxury, weekend and summer cruises. You can even designate which port you want to sail from and pre-book on-shore activities. Get there on the cheap with discounts on flights to Caldwell County and Caldwell County flights. Get more bang for your travel buck at Orbitz.

Frequently asked questions

Which airlines fly to Caldwell County?
Reserve an airfare with one of the 17 airlines that operate services to Nashville Intl. Airport (BNA) and get set for exciting new adventures. This popular airport is the entryway for Caldwell County. When you're ready to check off this region, these top carriers will get you there:

  • Air Canada - 42 flights to Caldwell County per month
  • WestJet - 20 flights to Caldwell County per month
  • British Airways - 16 flights to Caldwell County per month

How much is a flight to Caldwell County?
The cost for a round-trip flight to Caldwell County this week fluctuated from $175 to $706. If you were traveling one-way out of Chicago (ORD), you could have nabbed tickets from just $89.
How to book the cheapest flight to Caldwell County?
Snapping up cheap flights to Caldwell County is as simple as booking with Orbitz. But if you'd like to make sure you're walking away with the best flight deals around, here are some tips worth following:

  • Depending on your departure city, click on the 'Nearby airports' function (located under the departure and arrival options). From time to time, other departure points offer more value for money.
  • If you're flexible with your travel itinerary, click on the 'Show flexible dates' option. You'll see the flight deals for the days around your chosen departure. Fares often vary depending on the day of the week.
  • Select 'Show options' to refine your search results. You can choose your preferred seating class and airline here. Under 'Sort & Filter' to the left, you can even select whether you'd like to fly in the morning, afternoon or evening.
  • If you've worked out your travel dates, reserve your flight. Ticket prices generally increase as the departure date nears.
  • Make serious savings on your trip by bundling your hotel, flights and car rentals into a package deal. Your wallet will thank you.
  • Flying during peak season can mean steep airfares. Try to plan your vacation outside of popular periods, such as Easter, Thanksgiving and school breaks.

What is the best time to book a flight to Caldwell County?
Book your flights to Caldwell County in January. This is the perfect time of the year for low prices, followed by February and August. Snap up cheap flights and let your dream vacation come true with Orbitz.
What day of the week is the cheapest to book a flight to Caldwell County?
Make a booking on a Tuesday, Wednesday or Saturday. Typically, these are the cheapest days of the week to purchase fares to Caldwell County. The vacation of your dreams starts with an unbeatable flight deal!
What is the cheapest day of the week to fly to Caldwell County?
Everyone loves a bargain, so we recommend flying out earlier in the week to nab cheap flights to Caldwell County. Orbitz data from 2020 shows you can snap up the best deals on flights departing on Mondays. Tuesday is the next cheapest day, while Saturdays are the dearest. Many people like to start their trip at the weekend, so leave those Saturdays for catching up with friends.
What is the cheapest month to fly to Caldwell County?
Consider jetting off in August if you're on a tight budget. Orbitz data shows that this is generally the best month for cheap flights to Caldwell County. June is when ticket prices are at their most expensive.
Which airlines allow free cancellation?
Orbitz makes it a cinch to find airlines offering fare flexibility. Simply select "Filter by flexible change policies" when searching for your flights and hey presto! We'll show you options that include free cancellation, no change fees and of course, the best price.
What do I need for the flight to Caldwell County?
Flying can be a joy if you're well prepared! Make your journey a relaxing one with the following handy hints:

  • Before you step foot on the plane, you'll need to present some sort of government-issued ID, like your passport. You'll also need your ticket. If you're traveling with kids, check with your airline about which documents they require — if any.
  • Take some activities to keep you busy on your trip to Caldwell County. Books and electronic devices like laptops and e-readers are good ideas. Be sure to take a bottle of water as well. Even on a short flight, it's important to stay hydrated.
  • Even if you're traveling in the height of summer, take a hoodie or sweater on board with you. Cabins are notorious for getting downright chilly.

How do I get cheap first-class/business deals to Caldwell County?
If you think a first or business-class fare is beyond your reach, you may want to think again. Here are a few practical tips to help you land a premium flight to Caldwell County for a whole lot less:

  • Flexibility is everything. By being open to different travel dates, you'll have better odds of spotting a sale on your airfares.
  • Look for a low-cost carrier that has seats in business class. They often come with more space and a glass of Champagne — and a nicer price.
  • Bid for an upgrade in online auctions (if available) or upgrade your ticket through your flight loyalty scheme.

What is the best time to go to Caldwell County?
Caldwell County is a busy place in August, October and December. If you plan to head there during these months, it would be wise to book in advance to ensure you nab the best deals. Want to know what the summer's like in Caldwell County? Average daily temperatures typically fluctuate between 65 ºF and 85 ºF. Like most of the Northern Hemisphere, summertime starts June 20 here.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.