Chickasaw Vacations from $721

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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.

Pillow and Paddock B&B

$721

per person

Oct 16 - Oct 18

found 22 hours ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Louisville (SDF)

10/10 Exceptional! (52 reviews)

Courteous staff and the room was outstanding. It was our second stay at the inn. Everything is first class. We highly recommend it.

Reviewed on Dec 22, 2025

Cottonwood Airport & Expo Hotel Louisville

Shively

$859

per person

Oct 20 - Oct 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Louisville (SDF)

8.6/10 Excellent! (1,005 reviews)

Louisville Marriott Downtown

Downtown Louisville

$775

per person

Nov 7 - Nov 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Louisville (SDF)

9/10 Wonderful! (1,003 reviews)

Property was nice! Room was as expected! Valet/service was much to be desired! Room service snd bar service was some of the worst I’ve ever encountered! Was told by room service they had water; but if I wanted then I had to come get them myself! She wasn’t delivering them! Bartender in the hotel lounge was so bad it was laughable!! Told us she was doing us a favor by waiting on us! Lost her mind when I ask for 3 small bowls to put nuts in so our party of eight didn’t have to pass around the same cardboard cup she put them in!

Reviewed on Aug 16, 2026

Moxy Louisville Downtown

Downtown Louisville

$958

per person

Oct 26 - Nov 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Louisville (SDF)

9.2/10 Wonderful! (815 reviews)

Reviewed on Aug 26, 2026

Hyatt Regency Louisville

Downtown Louisville

$772

per person

Oct 1 - Oct 4

found 10 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Louisville (SDF)

8.8/10 Excellent! (1,005 reviews)

We had a great stay. The rooms were nice, clean, and well maintained. The staff were super friendly and accommodating for us convention go-ers. Cant beat the location either as it’s right next to the convention center and street live.

Reviewed on Aug 25, 2026

Where to stay in Chickasaw

Find the best Chickasaw areas and neighborhoods for the activities you enjoy most. Learn more about Chickasaw

A city skyline with various buildings, including a prominent KFC and a green-roofed structure.

Downtown Louisville

4 out of top 10 points of interest in this area

Explore "Museum Row" in the West Main District, catch a game at Louisville Slugger Field, or stroll across the pedestrian-only Big Four Bridge. Enjoy diverse attractions, restaurants, and the Louie Link skywalk.

A brown horse with a red halter, a person in a black shirt, and a crowd of people in the background.

Fairgrounds

1 out of top 10 points of interest in this area

While visiting Fairgrounds, you might make a stop by sights like Freedom Hall and Kentucky Kingdom.

A city skyline at dusk with illuminated buildings reflecting on the water.

Jeffersontown

Jeffersontown is known for its abundant dining options, and you can plan a trip to Jeffersontown Commons Shopping Center and Bluegrass Indoor Karting while you're in town.

A nighttime cityscape with a brightly lit bridge and a skyline featuring a prominent dome-shaped building.

St. Matthews

Major shopping destination with the fifth-largest mall in Kentucky, Mall St. Matthews, and smaller centers along Shelbyville Road. Don't miss the historic St. Matthew's Episcopal Church and Holy Trinity.

A narrow stream with a rocky bridge, surrounded by trees and greenery.

Phoenix Hill

While Phoenix Hill isn't home to many top sights, Nulu Market Place and Louisville Slugger Field are some notable places to visit nearby.

Chickasaw Hotel Deals

Galt House Hotel Trademark Collection by Wyndham

140 North Fourth Street Louisville KY

Fully refundableReserve now, pay when you stay

$143 nightly

$168 total

Sep 8 - Sep 9

Total with taxes and fees

9/10 Wonderful! (4,295 reviews)

"Just an extremely pleasant, relaxing experience, I enjoyed every bit of my stay."

Reviewed on Aug 26, 2026

Omni Louisville Hotel

400 S. 2nd Street Louisville KY

Fully refundableReserve now, pay when you stay

$175 nightly

$206 total

Aug 27 - Aug 28

Total with taxes and fees

Holiday Inn Express & Suites Louisville Downtown by IHG

800 W Market St Louisville KY

Fully refundableReserve now, pay when you stay

$89 nightly

$105 total

Aug 27 - Aug 28

Total with taxes and fees

8.8/10 Excellent! (1,765 reviews)

"Clean nice comfortable and gym was nice breakfast spread was excellent"

Reviewed on Aug 26, 2026

See all 2,096 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.