From Honky Tonks to Deep Dish: Our Family Road Trip from Nashville to Chicago

Travel

Apr 16

Most trips we take feel like a blur. But this one? It felt like a series of distinct smaller trips—each one with its own soundtrack, flavor, and charm. Over the course of ten days, we zigzagged from the sweet southern rhythms of Nashville, through Kentucky horse country, and into the towering, deep-dish-loving heart of Chicago.

Our arrival into Nashville was quite the adventure itself!

But let’s back up for a second. Because just getting to Nashville was half the adventure.

As we approached the city, our flight was rocked by turbulence unlike anything we’ve ever experienced—historic storms had slammed the midwest, and just moments before our arrival, a tornado touched down just north of the airport. We circled in the air for about an hour, eyes glued to the flight tracker, as the airport temporarily shut down. Then, in a narrow 20-minute window of clear skies between two bands of storms, our pilot made the call. We landed—safely, shakily, and with adrenaline still pumping. Welcome to Nashville!

Nashville: Music City

Our trip began in a city that needs no introduction: Nashville. We checked into the Gaylord Opryland Resort, which is less "hotel" and more like "indoor Southern village meets jungle oasis." Waterfalls, glass ceilings, and twinkle lights that feel like you're walking through a country song.

Our first night was mellow—dinner on site and wandering the lush atriums, which was the perfect indoor activity given the storms were still raging outside!

After a good night’s rest, we kicked things off with a Hatch Show Print letterpress workshop inside the Country Music Hall of Fame Museum. Hatch is iconic in the music industry for creating signature inked concert posters for all the greatest stars. We had a quick bite at the museum’s Bajo Taco (nothing impressive, but convenient!) before catching Jaime Hanna in a Musician Spotlight session. We toured the museum's many floors of exhibits, but the highlight was walking amongst all the rhinestone-studded guitars and outfits worn by country’s greatest musicians.

Next up was the RCA Studio B Tour, a must when in Nashville! We sat at the same piano Elvis recorded over 200 hits and stood in the spot where countless other artists belted out their Billboard Hits.

That afternoon, we wandered Broadway. Yes, with kids—and yes, it’s totally doable (and kind of magical) before dark. Walking down the sidewalk, you pass dozens of venues where bands and singers hope to make their break. The streets are crowded with party tractors and bachelorette parties, so it’s a bit like Vegas meets Country. We grabbed dinner at Assembly Food Hall, which had incredible food options and, you guessed it, more live music!

The next day, we took a tour of the iconic Grand Ole Opry, conveniently located next door to the Gaylord Opryland Hotel. We all agreed that although the hotel was fabulous, it was a bit outside of all the hustle and bustle of the city (15 ish minutes or so), and that if we were to go again, we would have stayed downtown and made a day trip to visit the hotel and Grand Ole Opry. Nevertheless, we still thoroughly enjoyed our stay, and if a retreat from Country Vegas is what you are after, the Opryland might just be for you!

After touring the Opry, we drove out to the Loveless Cafe for their famous mouth-watering biscuits. Being vegetarians, we stuck to sides, and yet we all left incredibly full and satisfied!

That afternoon, we popped down to Franklin—think charming boutiques and that elevated small-town feel. We mural-hopped through 12 South and The Gulch, visited the Gibson Garage for a guitar-themed souvenir (No, not a lifesize guitar, an ornament for our tree!), then capped it all off with a Fleetwood Mac tribute show at Wine City.

Before leaving town, we made one last Nashville stop: a tour of the Ryman Auditorium—the "Mother Church of Country Music." Then we hit the road toward bourbon country.

Kentucky: Horses & History

Our home base in Louisville was this Airbnb in the NuLu District, walkable to nearly all the best restaurants in Louisville and just a block away from a life-changing scoop at Louisville Cream. I highly recommend this location and the Airbnb we stayed at! Dinner that first night was at Agave & Rye, for some of the most incredible vegetarian tacos I’ve ever had.

The next day, we made the short trek to Lexington for a Thoroughbred Horse Farm Tour, booked through Viator, where we met foals, toured farms, and learned how racehorses are trained from the ground up. Afterward, the kids let loose at a playground before dinner at Carson’s (where I tried my first Old Fashioned!). The drive alone to Lexington was lovely and so picturesque with the white-picket fence-lined farms. I wish we had had more time to explore this quaint city, but we had an important tour to head back to Louisville for the next day!

Early the next morning we were up before the sun for a 7:30 AM horse workout viewing at the home of the famous Kentucky Derby: Churchill Downs. Watching the sunrise over the track felt like something out of a movie scene! We checked out the Kentucky Derby museum before popping into the historic Brown Hotel for lunch at J. Graham’s Café and my first ever Mint Julep. Southern bucket list = checked.

Then it was time for the moment the boys were waiting for: The Louisville Slugger Museum & Factory tour! A highlight for Dan was holding one of Babe Ruth’s famed bats. Lucas loved seeing the behind-the-scenes mechanics of how the bats are made (plus the souvenir toy bat every tour attendee brings home!).

Our trip to Kentucky was complete, next stop: Chicago!

Chicago: Big City Magic

We broke up the five-hour drive north with a pitstop in Indianapolis—stretching our legs near Monument Circle and enjoying a satisfying vegetarian lunch at Café Patachou.

We arrived in Chicago with plenty of light left to explore. We dropped off the rental car and checked in at the InterContinental on Magnificent Mile. It was walkable to Navy Pier, where we tested our first deep dish at Giordano’s... and left kind of underwhelmed (but we weren’t giving up yet!).

For our first full day in Chicago, we started with photos at The Bean, the kids climbed and played their way through Maggie Daley Park, grabbed lunch at Native Foods, browsed the Harold Washington Library and indie favorite Exile in Bookville, and made a quick stop at the iconic Chicago Theater.

We Ubered up to Wrigleyville in the afternoon to peek at Wrigley Field and shop the team store. That night? Redemption in the form of Pequod’s Pizza, whose deep dish won over Dan and Lucas.

The next day, we wandered the Magnificent Mile—Starbucks Reserve and the newly opened Harry Potter Shop, which were cool to see but not must-dos. The real gem was the Lincoln Park Zoo and Conservatory—both free and kept us entertained all day. That night, we stopped at Osteria Del Pastio for their homemade pastas and cacio e pepe.

Our final full day started with a surprise favorite: Montrose Point Bird Sanctuary. With my recent obsession with bird-watching, I might have been the only one excited about this stop, but it turned out to be a favorite for us all! The park also has a showstopper skyline view, excellent beaches, and birds galore—it was the perfect way to spend several hours (although, I would have stayed longer!). Lunch followed at Can’t Believe It’s Not Meat, which had excellent vegetarian and vegan options, but we all agreed that Native Foods was a better pick.

Post lunch, it was time for the grand finale: a Chicago Architecture Boat Tour. Floating through the city, we learned about the unique history and architecture of Chicago. It was definitely a highlight of the trip, and I wish we had done it on our first day to have a better appreciation as we explored the city.

We ended our trip with a final deep dish from Lou Malnati’s. Kendall and I declared it our favorite—though let’s be real: we’re a NY pizza family at heart. The thing to remember about Deep Dish—it’s just not the same as pizza, it’s honestly its own unique food form. Good, but no substitute for pizza.