Chickasaw Vacations from $389

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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.
Holiday Inn Louisville Airport South by IHG

Holiday Inn Louisville Airport South by IHG

3 out of 5
Save 100% on your flight
Price was $644, price is now $389 per person
$389
per person
Jan 6 - Jan 11
found 6 hours ago
Roundtrip flight included
New York (NYC) to Louisville (SDF)
8.8/10 Excellent! (765 reviews)
I've always had good luck with holiday inn. I have never encountered a dirty location. Rooms were comfortable, staff was friendly and breakfast was delicious. What more could you ask for? Oh, the location was a definite plus!

Reviewed on Nov 30, 2025

Caesars Southern Indiana - A Caesars Rewards Destination

Caesars Southern Indiana - A Caesars Rewards Destination

3.5 out of 5
Save 100% on your flight
Price was $906, price is now $467 per person
$467
per person
Jan 6 - Jan 11
found 6 hours ago
Roundtrip flight included
New York (NYC) to Louisville (SDF)
8.2/10 Very Good! (1,002 reviews)
This is an excellent venue except for the smoky air. While we had a king non-smoking room unfortunately air is circulating throughout the facility and the unpleasant cigarette smoke smell permeates all rooms. If that doesn’t bother you you’re going to enjoy your stay.

Reviewed on Nov 25, 2025

Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Save 100% on your flight
Price was $843, price is now $541 per person
$541
per person
Jan 6 - Jan 11
found 6 hours ago
Roundtrip flight included
New York (NYC) to Louisville (SDF)
9/10 Wonderful! (1,003 reviews)
Room was clean. Holiday ambiance was great. Good food.

Reviewed on Nov 29, 2025

Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Save 100% on your flight
Price was $721, price is now $471 per person
$471
per person
Jan 6 - Jan 11
found 6 hours ago
Roundtrip flight included
New York (NYC) to Louisville (SDF)
8.8/10 Excellent! (1,005 reviews)
Room was perfect! Staff members were friendly. Amenities were well kept! We would stay again.

Reviewed on Nov 30, 2025

Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
Fairgrounds
Save 100% on your flight
Price was $694, price is now $455 per person
$455
per person
Jan 6 - Jan 11
found 6 hours ago
Roundtrip flight included
New York (NYC) to Louisville (SDF)
8.8/10 Excellent! (962 reviews)
The Crown is always a go to for our family. Great staff, fantastic amenities, nice sit down bar area and wonderful full service dinig room. And lets not forget how clean it was and all sraff was very friendly.

Reviewed on Nov 30, 2025

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Where to stay in Chickasaw

Find the best Chickasaw areas and neighborhoods for the activities you enjoy most. Learn more about Chickasaw
Louisville showing signage and street scenes as well as a small group of people

Downtown Louisville

4 out of top 10 points of interest in this area
4/5(1,812 area reviews)

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.

Find hotels in Downtown Louisville

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
$93 nightly
The price is $110 total per night from Dec 10 to Dec 11
$110 total
Dec 10 - Dec 11
Total with taxes and fees
8.8/10 Excellent! (3,811 reviews)
Room was spotless and with a great view

Reviewed on Nov 28, 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
$72 nightly
The price is $85 total per night from Dec 10 to Dec 11
$85 total
Dec 10 - Dec 11
Total with taxes and fees
8.8/10 Excellent! (994 reviews)
Clean and spacious rooms, good staff, good location. Stay away from Al's Kitchen, however.

Reviewed on Nov 25, 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
$167 nightly
The price is $197 total per night from Jan 1 to Jan 2
$197 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
9.2/10 Wonderful! (1,701 reviews)
Clean and friendly staff. Hotel was close to lots of things to do.

Reviewed on Nov 26, 2025

Omni Louisville Hotel
See all 2,037 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Chickasaw

Ky Derby festival balloon glow.

Kentucky Exposition Center

4.5/5(628 reviews)

Learn about the events happening at Kentucky Exposition Center during your trip to Louisville. Experience the area's great live music and lively festivals.

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

Things to do

Kentucky Derby Museum

Kentucky Derby Museum - General Admission and Guided Track Visit

$22
per adult
90% of travellers recommend
Kentucky Derby Museum - General Admission and Guided Track Visit
Derby City Ghosts: Louisville Hauntings Tour

Lace, Lunacy, and Loss: Louisville Ghost Tours

$32
per adult
Lace, Lunacy, and Loss: Louisville Ghost Tours
Kentucky Derby Museum - Admission with Guided Track Visit

Kentucky Derby Museum - Admission with Guided Track Visit

$22
per adult
100% of travellers recommend
Kentucky Derby Museum - Admission with Guided Track Visit
See all activities in Louisville
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.