Chickasaw Vacations from $362

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Your Chickasaw Vacation

Our vacation packages to Chickasaw allow you to create your own adventure. Tailor your journey to your style and interests and make the most of your time in this exciting city. You'll want to sightsee during your trip to Chickasaw. Swing by popular attractions like Churchill Downs, Muhammad Ali Center and KFC Yum Center. Whatever your travel plans or the size of your budget, organizing a tailored Chickasaw vacation is simple with Expedia.

The Latest Chickasaw vacation packages

Price found within the past 48 hours. Click for updated prices.
Best Western Premier Airport/Expo Center Hotel

Best Western Premier Airport/Expo Center Hotel

3.5 out of 5
Shively
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
New York (JFK) to Louisville (SDF)
8.6/10 Excellent! (851 reviews)
nice hotel and breakfast

Reviewed on Jul 10, 2025

Caesars Southern Indiana

Caesars Southern Indiana

3.5 out of 5
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
New York (LGA) to Louisville (SDF)
8.2/10 Very Good! (1,003 reviews)
I would not recommend the property for those that do not live near! Nit many fining choices and I was unable to turn off the cold air.

Reviewed on Jul 9, 2025

Bourbon Barrel Inn Bed & Breakfast

Bourbon Barrel Inn Bed & Breakfast

3 out of 5
Old Louisville
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
New York (LGA) to Louisville (SDF)
No reviews
The Pepin Mansion Historic B&B

The Pepin Mansion Historic B&B

4 out of 5
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
New York (NYC) to Louisville (SDF)
9.8/10 Exceptional! (598 reviews)
Ryan is a top notch manager! The prime location downtown created a very walkable stay. Breakfast was truly special! The food was delicious and beautifully presented. It was fun to meet other guests during our breakfast. All of this is set in a gorgeous 1800’s mansion that has been lovingly restored.

Reviewed on Jul 6, 2025

TownePlace Suites by Marriott Louisville North

TownePlace Suites by Marriott Louisville North

3 out of 5
per person
Aug 26 - Aug 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
9.2/10 Wonderful! (561 reviews)
Beautiful room. Nice and clean.

Reviewed on Jul 2, 2025

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Discover the most popular places to visit in Chickasaw

Ky Derby festival balloon glow.

Kentucky Exposition Center

4.5/5(628 reviews)

During your trip, find out what's happening at Kentucky Exposition Center, a top convention center in Louisville. Experience the area's lively festivals and great live music.

Kentucky Exposition Center
Churchill Downs showing horseriding and land animals as well as a small group of people

Churchill Downs

4.5/5(551 reviews)

Find more than mint juleps to enjoy at this iconic racetrack, best known as the annual host of the Kentucky Derby.

Churchill Downs
Louisville Slugger Museum showing interior views

Louisville Slugger Museum

4.5/5(606 reviews)

Baseball is part of the American fabric. See where one important tool for this sport is produced in the factory that makes ball games possible.

Louisville Slugger Museum

What to do in Chickasaw

Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

$30
per traveler
Self Guided Driving Tour to Four Kentucky Bourbon Distilleries
Historic Old Louisville Walking Tour

Historic Old Louisville Walking Tour

$15
per adult
100% of travellers recommend
Historic Old Louisville Walking Tour
Louisville: Photoshoot Walking Tour with Pictures

Louisville: Photoshoot Walking Tour with Pictures

$55
per adult
Louisville: Photoshoot Walking Tour with Pictures
See all activities in Chickasaw

Chickasaw Hotel Deals

Galt House Hotel Trademark Collection by Wyndham
Galt House Hotel Trademark Collection by Wyndham
4 out of 5
140 North Fourth Street, Louisville, KY
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $169 total per night from Aug 10 to Aug 11
$169 total
Aug 10 - Aug 11
Total includes taxes and fees
8.8/10 Excellent! (3,423 reviews)
"Great downtown location and friendly staff."

Reviewed on Jul 8, 2025

Galt House Hotel Trademark Collection by Wyndham
Crowne Plaza Louisville Airport Expo Ctr by IHG
Crowne Plaza Louisville Airport Expo Ctr by IHG
3.5 out of 5
830 Phillips Lane, Louisville, KY
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $111 total per night from Jul 21 to Jul 22
$111 total
Jul 21 - Jul 22
Total includes taxes and fees
8.6/10 Excellent! (640 reviews)
"Right next to airport. Clean property. Friendly staff. Common location for events so there are times it is super busy. Have stayed here numerous times."

Reviewed on Jul 7, 2025

Crowne Plaza Louisville Airport Expo Ctr by IHG
Omni Louisville Hotel
Omni Louisville Hotel
4 out of 5
400 S. 2nd Street, Louisville, KY
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $187 total per night from Aug 8 to Aug 9
$187 total
Aug 8 - Aug 9
Total includes taxes and fees
9.2/10 Wonderful! (1,511 reviews)
"Perfect"

Reviewed on Jul 7, 2025

Omni Louisville Hotel
See all 1,933 properties in Chickasaw
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.

Find the Best Chickasaw Vacation Packages

Chickasaw Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Louisville Intl. Airport (SDF)
Top Sights
Kentucky Kingdom, Louisville Slugger Museum and Louisville Zoo

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Frequently asked questions

How much does a Chickasaw vacation package cost?
You can pick up a vacation package to this destination from $362 on Expedia. However, how much your vacation to Chickasaw costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Chickasaw?
If you'd like to book a cheap Chickasaw vacation package, consider traveling in September, November and December. You'll usually find lower prices on accommodations and flights during these quieter months --- ideal for budget-conscious travelers.
How many days is enough for Chickasaw?
With a well-planned itinerary, you can easily visit the top Chickasaw sights in a handful of days. But if you'd like to discover hidden spots or go on day trips, think about booking your Chickasaw vacation for longer.
How to find the best Chickasaw package deals?
Begin your search for a Chickasaw package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Chickasaw package deal straight away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Chickasaw adventure off to a flying start.
Is it cheaper to book a Chickasaw vacation as a package?
You can enjoy significant savings on your Chickasaw getaway by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to view some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Chickasaw?
If you have your Chickasaw vacation dates finalized, book as soon as you can to grab some incredible deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for quick escapes.
Does Expedia offer Book Now, Pay Later Chickasaw vacation packages?
Your Chickasaw break is meant to be an escape from your busy life, not a source of money worries. So to give you a bit more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.