Winter Getaway: Escape to Louisville on a budget

You don't have to be a fan of the Kentucky Derby or baseball to enjoy a trip to Louisville, the state's largest city. Founded in 1778, it's also one of the oldest cities west of the Appalachian Mountains. Today, Louisville also hosts other annual festivals and sporting events besides the Derby. The city also has museums, performing arts centers and plenty of food and drink offerings to appease residents and visitors alike.

Whether you're seeking an immediate getaway or you're looking to plan ahead based on the cheapest fares, look at these upcoming flights between Chicago and Louisville, which we pulled from travel site Skyscanner.

We've also included top-rated hotels, restaurants and attractions in Louisville, to get you started on planning your ideal getaway.

(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.)


The cheapest flights between Chicago and Louisville are if you leave on January 19 and return from Kentucky on January 21. American Airlines currently has roundtrip tickets for $154.

American Airlines also has tickets at that price point in December. If you fly out of Chicago on December 3 and return from Louisville on December 6, American Airlines can get you there and back for $154 roundtrip.


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

The Brown Hotel (335 W. Broadway)

Photo: Trip by Skyscanner

If you're looking to treat yourself, consider The Brown Hotel. The hotel is located close to the airport and has a 4.9-star rating on Skyscanner. Rooms are currently available for $129.

Dating back to the 1920s, this hotel was known to draw more than 1,200 guests for dinner dances. It's also known for something called the Hot Brown, an open-faced turkey sandwich with bacon and a delicate Mornay sauce. Attractions in the neighborhood include the Louisville Palace and Fourth Street Live. Other attractions include the Muhammed Ali Center.

"Beautiful, historic hotel, and they serve the original Hot Brown. This is a must have when visiting Louisville," wrote visitor Pamela.

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

Another 4.9-star option is The 21c Museum Hotel Louisville. Rooms are currently set at $159/night.

This hotel is located close to the airport. Attractions in the neighborhood include the Kentucky Museum of Art and Craft, the Muhammed Ali Center, and the Louisville Slugger Museum. Additional attractions include the Riverfront Plaza Belvedere.

The Seelbach Hilton (500 Fourth Ave.)

Photo: Trip by Skyscanner

A third option is The Seelbach Hilton. The 4.4-star hotel has rooms for $114/night. Set in the heart of Louisville, this hotel is close to Fourth Street Live and the Muhammed Ali Center, as well as the Riverfront Plaza Belvedere. Additional attractions include the Louisville Slugger Museum.


If you're looking for a popular spot to grab a bite, Louisville has plenty of excellent eateries. Here are a few from Skyscanner's listings to help you get started.

Garage Bar (700 E. Market St.)

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

Located in a former garage, this hip eatery boasts a menu with brick-oven pies, oysters, local and regional country hams and Southern inspired specialties. Choose from craft beers, seasonal cocktails and more than 75 Kentucky bourbon and rye whiskeys.

"We loved the ham bar and both the Brussel sprouts pizza and the sausage pizza. Plus, the concept is pretty cute," wrote visitor Krista.

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

Photo: Trip by Skyscanner

Another popular dining destination is Jeff Ruby's Steakhouse, with 4.9 stars from 11 reviews.

Styled after the great New York City steakhouses of long ago, this Jeff Ruby Steakhouse features a fresh sushi bar, and the menu includes dry aged USDA prime beef, local favorites and seafood entrees.

"Go here for a great view and one of the best steaks in town, " wrote reviewer Kelly. "It is a pricier option for dining in Louisville, but it's a great romantic spot for a night out."

Proof on Main (702 W. Main St.)

If you're looking for a solid place to grab a drink, plan to visit Proof on Main.

Located in downtown Louisville, this restaurant inside the award-winning 21c Museum Hotel serves cuisine from Italy and the American South. One of the stops along the Urban Bourbon Trail, Proof on Main's bar features more than 50 of Kentucky's finest bourbons plus cocktails.

"The drinks are creative and tasty," wrote Tyson. "But this place is not for people with shallow wallets. It is, however, a great starting point for a night out."

El Taco Luchador (938 Baxter Ave.)

Photo: Trip by Skyscanner

Finally, there's El Taco Luchador.

Decorated with Luchador masks, this quirky taqueria serves big tortas, house-made salsas and dips and, of course, tacos.

"The menu is nicely crafted, and has options for the picky eaters," wrote visitor Kelly.


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

Churchill Downs (700 Central Ave.)

Photo: Trip by Skyscanner

First up, here's Churchill Downs.

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.

Additional attractions include the Kentucky Derby Museum, featuring exhibits on the history of the race track and the Kentucky Derby.

"Churchill Downs is a staple in Kentucky culture and history--the place to see and be seen," wrote visitor Kelly.

Big Four Bridge (1101 River Road)

Photo: Trip by Skyscanner

Then, spend some time at Big Four Bridge.

Enjoy a two-mile trek on the Big Four, a pedestrian bridge connecting Louisville with Jeffersonville, Indiana on the other side. At night, the bridge is lit up in neon colors from dusk to about 1 a.m.

"The view of downtown Louisville cannot be beat. Plus, the hotdogs and ice cream are a great treat from the top of the bridge!" write visitor Theresa M.