Top travel picks: Getaway from Milwaukee to Louisville

You don't have to be a fan of the Kentucky Derby or baseball to enjoy a trip to Louisville. Positioned on the banks of the Ohio River along the Indiana border, it is the state's largest city. Founded in 1778, the city is one of the oldest cities west of the Appalachian Mountains. Today, it has annual festivals, museums, performing arts centers, sports happenings and plenty of food and drink offerings to appease residents and visitors alike.

Using travel site Skyscanner, we’ve sifted through the cheapest flights between Milwaukee and Louisville in the next few months, including some top-rated hotel options and beloved local attractions.

(Hoodline offers data-driven analysis of local happenings and trends across cities. Links included in the articles may earn Hoodline a commission on clicks and transactions. Prices and availability are subject to change.)

Cheapest Louisville flights

Currently, the cheapest flights between Milwaukee and Louisville are if you leave on May 31 and return from Kentucky on June 2. American Airlines currently has tickets for $264, roundtrip.

There are also deals to be had earlier in May. If you fly out of Milwaukee on May 6 and return from Louisville on May 10, American Airlines can get you there and back for $265 roundtrip.

Top Louisville hotels

Regarding where to stay, here are some of Louisville’s top-rated hotels, according to Skyscanner, that we selected based on price, proximity to things to do and customer satisfaction.

The Brown Hotel (335 W. Broadway)

Photo: Trip by Skyscanner

For an all-around top recommendation, consider The Brown Hotel. The hotel has a 4.9-star rating on Skyscanner, and rooms are currently available for $129.

Attractions in the neighborhood include the Louisville Palace, Fourth Street Live and the Muhammad Ali Center.

The 21c Museum Hotel Louisville (700 W. Main St.)

Another 4.9-star option is The 21c Museum Hotel Louisville, which has rooms for $159/night.

"A lovely boutique hotel in downtown Louisville. For the art lover, this is a must-stay place," wrote visitor Tyson. 

The Seelbach Hilton (500 Fourth Ave.)

Photo: Trip by Skyscanner

If you're looking for an inexpensive place to stay, try The Seelbach Hilton. The 4.4-star hotel has rooms for $114/night.

Set in the heart of Louisville, this hotel is close to the Riverfront Plaza Belvedere and the Louisville Slugger Museum.

Top picks for dining and drinking

Don't miss Louisville's food scene, with plenty of popular spots to get your fill of local cuisine. Here are a few of the top-rated eateries from Skyscanner's listings.

Garage Bar (700 E. Market St.)

If you're looking for a local favorite, head to the Garage Bar, which has an average of 4.9 stars out of 17 reviews on Skyscanner.

"This spot has great outdoor seating, and a classy, yet dive bar ambiance. This is the spot to catch the locals gathering before games, events or wandering the historical downtown streets," wrote visitor Kelly.  

Jeff Ruby's Steakhouse (325 W. Main St.)

Photo: Trip by Skyscanner

Also worth considering is Jeff Ruby's Steakhouse, with 4.9 stars from 11 reviews.

"This classic steakhouse is famous in Louisville. Go here for a great view and one of the best steaks in town," wrote Kelly.  

El Taco Luchador (938 Baxter Ave.)

Photo: Trip by Skyscanner

Also worth considering is El Taco Luchador. It has 4.9 stars from 11 reviews. 

"The menu is nicely crafted and has options for picky eaters. Stroll over here and eat some scrumptious tacos," wrote Kelly.

Featured Louisville attractions

To round out your trip, Louisville offers plenty of popular attractions worth visiting. Here are a few top recommendations, based on Skyscanner's descriptions and reviews.

Churchill Downs (700 Central Ave.)

Photo: Trip by Skyscanner

First up is Churchill Downs, with 4.8 stars from 57 reviews.

Opened in 1875, Churchill Downs has hosted the Kentucky Derby for more than 130 years. A popular horse racing venue, designated a National Historic Landmark in 1986, it can house up to 150,000 people during peak competitions.  

The Louisville Slugger Museum & Factory (800 W. Main St.)

Photo: Trip by Skyscanner

The Louisville Slugger Museum & Factory is another popular destination. It checks in with 4.8 stars from 54 reviews.

The museum is primarily dedicated to showcasing the history of the Louisville Slugger brand of baseball bats, as well as of baseball in general, with a combination of interactive exhibits and memorabilia displays.

The Frazier History Museum (829 W. Main St.)

Photo: Trip by Skyscanner

Finally, spend some time at The Frazier History Museum. It has five stars from seven reviews.

"In a nutshell, a fine weapons museum. The exhibits are more than just armaments, but I went with two young boys and they loved the weapons. Staff periodically present programs like a demonstration of 17th century sword fighting," wrote visitor Betsy. 

This story was created automatically using flight, hotel, and local attractions data, then reviewed by an editor. Click here for more about what we're doing. Got thoughts? Go here to share your feedback.