Escape from Chicago to Louisville on a budget

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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, 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.

Thankfully, there are plenty of regular, relatively-inexpensive flights between Chicago and Louisville. We pulled from travel site Skyscanner to provide you with a short list of flights and hotels handpicked with the trendy adventurer in mind.

(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 December 13 and return from Kentucky on December 17. United currently has roundtrip tickets for $153.

There are also deals to be had earlier 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 $161 roundtrip.


To plan your stay, here are some of Louisville's top-rated hotels, that we selected from Skyscanner's listings based on price 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.

This hotel is located close to the airport. Attractions in the neighborhood include the Louisville Palace, Fourth Street Live and the Muhammed 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.

Attractions near the hotel include the Kentucky Museum of Art and Craft, the Muhammed Ali Center, the Louisville Slugger Museum and 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 Riverfront Plaza Belvedere. Additional attractions include the Louisville Slugger Museum.


Louisville has plenty of topnotch dining options. Here are a few of the most popular, according to Skyscanner.

Proof on Main (702 W. Main St.)
Photo: Trip by Skyscanner

Don't forget the essentials: where to get a drink. For a popular option, check out Proof on Main, with 4.8 stars from 17 reviews.

Proof on Main at the award-winning 21c Museum Hotel in Downtown Louisville offers a combination of inventive food and beverages.

"A great bar in the 21c hotel," wrote reviewer Tyson. "The drinks are creative and tasty."

Jeff Ruby's Steakhouse (325 W. Main St.)
Photo: Trip by Skyscanner

Also worth considering is Jeff Ruby's Steakhouse.

Styled after the great New York City steakhouses of long ago, this Jeff Ruby Steakhouse has an energy all its own. The menu features dry aged USDA prime beef, as well as some local favorites.

"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

Finally, there's El Taco Luchador.

"Lets talk about this joint," wrote Kelly."Great on Tuesdays and with tequila. The menu is nicely crafted, and has options for the picky eaters."


Not sure what to do in Louisville, besides eat and drink? Here are two recommendations, provided by Skyscanner.

Kentucky Derby (700 Central Ave.)
Photo: Trip by Skyscanner

The top-rated visitor attraction in Louisville, according to Skyscanner, is Kentucky Derby.

The fastest any horse ever ran the high stakes race was Secretariat in 1973, at 1:59.40. The slowest run was by Stone Street who completed it in 2:15.20. With such a small margin between greatness and great failure, you can understand the excitement and anticipation inherent in this event that has been a part of Kentucky society since 1896. The big race, run at Churchill Downs, is the exciting culmination to a two-week festival that includes parades, concerts, and more.

The Louisville Slugger Museum & Factory (800 W. Main St.)
Photo: Trip by Skyscanner

Next, consider checking out The Louisville Slugger Museum & Factory.

The Louisville Slugger Museum is a museum 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 in a space of 16,000 square feet.
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