Chickasaw Vacations from $619

Name: Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)
Price range: $108 total

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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.

Hyatt Regency Louisville

Downtown Louisville

$619

per person

Dec 22 - Dec 24

found 15 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Louisville (SDF)

8.8/10 Excellent! (1,004 reviews)

Omni Louisville Hotel

Downtown Louisville

$689

per person

Feb 2 - Feb 4

found 12 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Louisville (SDF)

9.4/10 Exceptional! (2,202 reviews)

Hotel Distil, Autograph Collection

Downtown Louisville

$674

per person

Feb 2 - Feb 4

found 12 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Louisville (SDF)

9.6/10 Exceptional! (511 reviews)

Very luxurious hotel in a great location for great restaurants and some shopping. Close to some Louisville attractions like the Slugger museum, Angel’s Envy and Old Forester distilleries. The Repeal restaurant inside the hotel was truly a perfect experience!

Reviewed on Nov 10, 2026

Homewood Suites by Hilton Louisville Downtown, KY

Downtown Louisville

$1,033

per person

Dec 19 - Dec 26

found 1 day ago

Roundtrip flight included

Denver (DEN) to Louisville (SDF)

9.4/10 Exceptional! (1,009 reviews)

This was one of the best moderate price hotels in which we’ve ever stayed. The hotel was beautifully decorated; room was spacious and comfortable; staff were great and breakfast was exceptional with a huge variety with lots of toppings and touches. Location was perfect as well for our downtown walking exploration.

Reviewed on Nov 13, 2026

Wingate by Wyndham Louisville East

Jeffersontown

$877

per person

Dec 19 - Dec 26

found 1 day ago

Roundtrip flight included

Denver (DEN) to Louisville (SDF)

8.6/10 Excellent! (1,007 reviews)

Not impressed with this place at all, walk in all lighting is dim and depressing, room is worn and furniture with soils. Breakfast buffet was a joke and was supposed to be the best around. Front desk people rarely at the counter that is also in a dark corner like they don’t want you to see them. Room service: asked them to service the room, new towels were replaced but no toilet paper and they didn’t bother to vacuum. Plumbing in the shower a mess, toilet you have to hold down for it to flush. Unacceptable hotel

Reviewed on Nov 14, 2026

Where to stay in Chickasaw

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

A steamboat docked at a pier with a bridge in the background.

Downtown Louisville

3 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.

Chickasaw Hotel Deals

Galt House Hotel Trademark Collection by Wyndham

140 North Fourth Street Louisville KY

Fully refundableReserve now, pay when you stay

$130 nightly

$152 total

Nov 24 - Nov 25

Total with taxes and fees

The Brown Hotel

335 W Broadway Louisville KY

Fully refundableReserve now, pay when you stay

$122 nightly

$143 total

Nov 23 - Nov 24

Total with taxes and fees

9.4/10 Exceptional! (1,482 reviews)

"Great hotel. Historic and well maintained. Food and service at the bar is the best of anywhere you can go."

Reviewed on Nov 14, 2026

Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

4520 Poplar Level Rd Louisville KY

Fully refundableReserve now, pay when you stay

$92 nightly

$108 total

Nov 15 - Nov 16

Total with taxes and fees

See all 2,098 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.