Where Chicago Goes: Less Than 24 Hours in Louisville

What to do in Louisville

Welcome to Where Chicago Goes, a series offering itineraries for cities frequently visited by Chicagoans. These are not far away destinations. These are places many of us used to call home, cities where our parents have retired, and where we often fly for work and play. For our second installment, we headed to Louisville, Kentucky, one of America’s oldest cities.

Kentucky Fried Layover

The world knows Louisville for its bourbon, indie art scene, and Kentucky Derby. I know Louisville for its late-night prohibition-era lounges and brunch. That is because my time here is usually spent between the hours of 8 p.m. – 11 a.m., as a layover from my in-law’s place in Alabama to Chicago. I’ve never seen the contemporary art of 21C or the legendary Muhammad Ali Center, which, according to their website, is not just an experience but “a journey into the heart of a champion.” I’m missing out, but I am not alone. If you’ve got only 24 hours (or less) to spend in one of America’s oldest cities, here’s how to use them.

Where to Stay

What to do in Louisville
Image: Gralehaus

If your main concern is convenience and cleanliness over posh and pampering, I’d suggest an Airbnb in a neighborhood like The Highlands or Clifton, where bars, restaurants, and decent coffee is well within walking distance.

If you have never tried Airbnb, I recommend booking as far ahead as possible for the best selection and pricing. Don’t be afraid to ask your host a ton of questions before confirming; I always do. Make sure at least 95% of their reviews are positive, and they don’t have a habit of canceling at the last minute. For extra peace of mind, book with a superhost. Superhost is a status Airbnb gives those who, for at least a year, never cancel on any guest, are known to be responsive and available, and maintain 5-star reviews at least 80% of the time. For more info, visit Airbnb.

Another option? Book a room at the Gralehaus, but keep in mind that during the high season rooms fill quickly. More on Gralehaus later.

Where to Eat

What to do in Louisville
Image: Gralehaus Facebook
What to do in Louisville
The Silver Dollar
What to do in Louisville
The Silver Dollar


Just off Bardstown Road in the Highlands, you’ll find Safai Coffee Shop. Full of natural light and strong wi-fi, it’s a pleasant way to start a day away from home. They’re usually open from 6:30 a.m. – 10 p.m., with ample parking in the back. The coffee here is smooth thanks to their branded beans, available for purchase.

Safai Coffee Shop, 1707 Bardstown Rd., Louisville, KY 40205 (The Highlands)


Put your kale cleanse on ice for a moment to appreciate the calorie bender that is southern cooking: grits and butter, biscuits and pork, chicken and waffles, waffles and steak, chicken fried steak.

If you’re in town on a weekday, ahead of the weekend brunch humdrum, I suggest Gralehaus, which gets the credit for being the city’s only committed breakfast and beer service. Housed inside a beautiful old Victorian home, this café and inn offers quaint indoor and outdoor seating and a beer garden in the rear. A glossy wood floor and ceiling complement black tile and brick inside. Their tap selection includes a variety of craft beers, coffee, sodas, and even house brewed kombucha. Made-from-scratch, the food here is amazing. Seriously. Try the Lamb and Grits with a pale ale or the Biscuit and Duck Gravy. Make sure to get a biscuit on the side – which is flaky but hearty.

Make the layover even more special by booking a room in one of their three charming suites. My favorite? St. Brigid’s Deluxe, a romantic suite full of luxury: a chandelier, a soaking tub, velvet curtains and first-class amenities. Before calling it a night, dine at the Holy Grale, Gralehaus’ sister restaurant with which they share the beer garden, and wake up to the best beer and breakfast of your life. Then return home to that kale diet and gym routine.

Gralehaus, 1001 Baxter Ave, Louisville, KY 40204 (The Original Highlands)

Lunch and Dinner

For an unforgettable lunch, dinner, and weekend brunch look no further than The Silver Dollar. This was the first restaurant I ever tried in Louisville, and I never leave the city without revisiting it at least once. The menu is dependably fantastic. The cocktails may be the best in the city. Try the fried pickles, fried catfish, chicken and waffles and the spoon bread with grits. Wash it down with a few glasses of bourbon punch. Something so good must be good for you.

The Silver Dollar, 1761 Frankfort Ave, Louisville, KY 40206 (Clifton)


What to do in Louisville

What to do in Louisville
What to do in Louisville

If you’ve already pre-gamed at The Silver Dollar, then end the evening someplace dark and mysterious.  Mr. Lee’s is the speakeasy of the moment. It checks all the boxes: no signage outside, quirky details (in the lounge, pull on a lever to alert your bartender it’s time to refill or close the tab), a smartly dressed, talented mixologist, and a thirsty hipster following. It’s the Violet Hour of the south.

Mr. Lee’s, 935 Goss Ave, Louisville, KY 40217. Closed Monday and Tuesday. (Germantown)

Another excellent option for the libation aficionado, Meta is a hip speakeasy with sparse plush seating and dimly lit chandeliers. On their menu — yes, they have a menu — classic cocktails are listed alongside unique take on each. Try their version of a Manhattan.

Meta, 425 W Chestnut St., Louisville, KY 40202 (Downtown)

Think I missed something? Let me know in the comments below, or on TwitterFacebook, or Instagram.

All photos were taken by Kari of Chicagoings.com unless otherwise noted. Be sure to contact each company before your visit for current information and prices. All opinions expressed here are those of Kari Herrera and are not indicative of those held by the New Orleans Convention and Visitors Bureau or any other entity.