Chicago and Nashville Travel Guide: The Final Leg of Our Epic 11,775-Mile Cross-Country Journey

Chicago and Nashville Travel Guide: The Final Leg of Our Epic 11,775-Mile Cross-Country Journey 

This post is from Marrying Your Passions: The DINK Travel and Adventure Podcast. If you're a childfree couple who loves travel, road trips, and turning work trips into adventures - you're in the right place. Subscribe wherever you listen to podcasts!

In 2024, we logged 11,775 miles across the country - and our latest episode reflects on the final stops of that epic journey: Chicago and Nashville. This wasn't just a vacation. Alicia had a week-long work conference in Chicago, and instead of her flying in solo while Nathan stayed home, we turned it into an adventure. We figured out how to make it work - Nathan explored the city while Alicia was in meetings, and we turned what could have been a boring work trip into an unforgettable part of our cross-country journey.

Chicago: Where Deep Dish Dreams and Lakefront Runs Meet

We spent a full week in the Chicago area, camping at the beautiful Chicago Northwest KOA Holiday in Union, Illinois. But here's the thing: Alicia was at a work conference most of the week. This wasn't a vacation - this was us refusing to let work get in the way of adventure. While Alicia was in conference rooms and meetings Monday through Sunday morning, Nathan explored the city solo (and honestly had the time of his life).

Yes, the campground is about an hour from downtown Chicago, but here's why that's actually perfect: you get the serene campground experience (think lush grasslands, bunnies hopping across open fields, clean facilities) with easy access to the city.

Running the Iconic Lakefront Trail

While Alicia was at her conference, one of Nathan's solo adventures was a 10-mile run on Chicago's Lakefront Trail, starting at Navy Pier. If you've never experienced this, picture this: lanes roped off in Lake Michigan for swimmers training for triathlons, beaches packed with people, and water so gorgeously teal-blue you'd swear you were in Florida (until you touched it). The trail offers stunning views of the city skyline, easy access to restaurants and restrooms, and that perfect Chicago summer vibe.

Wrigleyville: Baseball, Massage, and Alamo Drafthouse

A day in Wrigleyville is a must. Wrigley Field sits right in a neighborhood, which gives it a completely different feel than stadiums built in the middle of nowhere. We splurged on good seats - and it's worth it. Park in someone's garage (locals rent them out on game days), walk through the bustling streets, grab food at one of dozens of restaurants, and soak in the atmosphere.

Pro tip: There's an Alamo Drafthouse in the same neighborhood. It was Nathan's third Alamo of the trip, and yes, he went to see Twisters after the game. Living his best life.

Deep Dish Pizza: Lou Malnati's Delivers

You cannot visit Chicago as vegetarians and skip deep dish pizza. We went to Lou Malnati's in Elk Grove - true Chicago style with all that glorious sauce on top. Build your own with extra garlic, and prepare to need a fork. It's not everyday pizza, but when you're in Chicago, it's required eating.

One Chicago Filming Locations

For fans of Chicago Fire, Chicago Med, and Chicago PD: Nathan geeked out visiting the real filming locations. Firehouse 51 (actually Fire Department 18) still has the Squad 3 and Ambulance 61 signs on the doors. Gaffney Medical Center is actually Rush University Medical Center. District 21 is the UIC Police Headquarters. And Molly's Pub? That's inspired by Lottie's Pub in Bucktown - and yes, Nathan got the hat that says "Lottie's by day, Molly's by night."

The food at Lottie's was fine, but the vibe is what makes it special. It's a true neighborhood bar where locals go to unwind, watch games, and catch up. If we lived in that neighborhood, we'd be regulars.

Coffee Stop: Lincoln House & Co.

In Huntley, about 15 minutes from our campground, we found Lincoln House & Co. Coffee and wine bar. Incredible avocado toast, unique espresso drinks, delicious cold brew, and a cute outdoor seating area. We went twice. That's how good it was.

Anniversary Dinner: Abbondanza Cucina Italian

We wrapped up our Chicago week with anniversary dinner at Abbondanza in Marengo - one of the few evenings we actually got to spend together since Alicia's conference kept her busy all week. This was a gem - small, family-owned feel, exceptional service (pretty sure we met the owner), and delicious Italian food. They have build-your-own pasta dishes, which we love. Nathan got sambuca, we both got fettuccine Alfredo (because are you ever too sick for fettuccine Alfredo?), and the whole experience was exactly what we needed.

Pro tip: Locals were constantly coming in for takeout, and the staff knew them by name. That's always a good sign.

Nashville: Music City, Moonshine, and Making Work Trips Work

After Chicago, we drove eight hours south to Nashville, staying at Two Rivers Campground - about 20 minutes from Lower Broadway. This was Nathan's second time in Nashville, Alicia's first real experience with the city, and honestly, we didn't spend as much time here as Chicago. But what we did? Worth it.

Buttermilk Ranch: Brunch Worth the Wait

Our first morning, we went to The Butter Milk Ranch for brunch. This place was packed on a Tuesday. We sat at the bar because tables had a wait. Beautiful interior, spacious with tons of windows and gorgeous wood everywhere. The cold brew concoctions were creative and delicious, and the food lived up to the hype. If it's called The Butter Milk Ranch, it's going to be good.

Moonshine Tastings: Ole Smoky Takes the Crown

We're fans of moonshine tastings, and we've done a lot of them - Gatlinburg, Branson, all over. But Ole Smoky's Nashville location is hands-down the best we've experienced.

Here's the setup: It's a huge standalone building with two sides. One side has a giant store with all the merchandise and a massive tasting bar in the center. The other side is a full bar where you can order cocktails, plus a food window serving tacos and other bites.

The genius part? During your tasting, they give you personalized cocktail recommendations for the bar side. Our tasting guide had us tell the bartender to make a PB&J cocktail using their peanut butter whiskey and blackberry moonshine - and it was incredible.

The whole experience felt personal, not scripted. The guy took his time, made it fun, and genuinely wanted us to find flavors we loved. (Compare that to some Gatlinburg locations where it feels like you're on a factory line listening to the same memorized jokes.)

Lower Broadway: Tootsies and Live Music

We walked Lower Broadway in the rain (because summer in the South) and ended up at Tootsies - the iconic honky tonk with three floors of live music. The food is standard bar food, but you're not there for the food. You're there for the atmosphere, the bands on every level, and the Nashville energy.

Fair warning: If you're short like Alicia, those tall wooden barstools are a hazard. She nearly knocked hers over trying to hop down. Everyone thought she was drunk. She wasn't - just too short for the furniture.

The Final Stop: Loves RV Stop in Cordele, Georgia

Our last night before heading home to Florida, we stayed at a Loves RV stop in Cordele, Georgia - and it blew our minds.

This wasn't your typical truck stop parking lot. It's a fully enclosed, gated RV park with a code for entry. Every site in the middle was pull-through (thank goodness, because we never learned to back up). Concrete pads, full hookups, 50 amp service, clean shower house, laundry facilities, and - this is the coolest part - a dog wash building.

There was even a communal fire pit and playground area. It cost about $50 for the night. You're not going to spend a week there, but for an overnight stop while traveling? Absolutely perfect. Clean, safe, and the 24-hour Loves store has everything you need.

We walked over for food that night and breakfast the next morning. No complaints.

The Bigger Picture: What We Learned After 11,775 Miles

This trip wasn't about seeing how many miles we could drive or how many campgrounds we could visit. It was about refusing to wait for the "perfect" conditions.

Alicia had two work conferences during the summer - one in Denver, one in Chicago. We could have said, "Well, that ruins our summer travel plans." Instead, we said, "How do we make this work?" She got a desk setup for the back of the car, we mapped out campgrounds near her conference locations, and Nathan turned solo days into tourist adventures while she worked.

Was it perfect? No. We both got sick at different points. It rained. We drove through storms. We spent money we're still paying off. But we also experienced things we never would have if we'd waited for "someday."

Here's the truth: There will always be a reason not to go. Not enough money. Not enough time. Not the right season. Too much work. The kids' schedules. The pets. The house. The list goes on.

But if you're childfree like us - if you're DINKs with the flexibility to say "why the hell not?" - then what are you actually waiting for?

You don't need the perfect RV with a washer and dryer. You don't need six weeks off work. You don't need your entire friend group to align their schedules. You just need to start.

Do two miles of the trail instead of twenty. Stay one night instead of a week. Turn a work trip into a mini-adventure by adding a day and exploring the city. Grab that local coffee or try that restaurant or visit that museum for just one exhibit.

The magic happens in the margins - in the unexpected detours, the local recommendations, the moonshine guy who makes it fun, the campground that exceeds expectations, the sunset you didn't plan for.

We're not saying quit your job and live in a van. We're saying: look at your life right now and ask, "What small thing could I do this week to incorporate what I love?"

Maybe it's a Saturday morning hike you've been putting off. Maybe it's finally trying that restaurant you drive past every day. Maybe it's saying yes to the work trip and adding two days to explore.

Don't let the image of the "ideal" trip prevent you from taking the real one.

Planning Your Own Chicago or Nashville Trip?

Chicago:

• Stay at Chicago Northwest KOA Holiday for the best of both worlds (nature + city access)
• Run the Lakefront Trail early morning to beat crowds and heat
• Splurge on good Wrigley Field seats if the Cubs are in town
• Get deep dish at Lou Malnati's (multiple locations)
• Visit Lincoln House & Co. in Huntley for incredible coffee and avocado toast
• Abbondanza Cucina in Marengo for authentic Italian with a neighborhood feel
• Check out One Chicago filming locations if you're a fan
• Give yourself a full week - there's too much to see in a weekend

Nashville:

• Two Rivers Campground is 20 minutes from Lower Broadway
• Don't skip The Butter Milk Ranch for brunch (get there early or prepare to wait)
• Ole Smoky's Nashville location is the best moonshine tasting we've done - do the tasting, then order cocktails at the bar
• Lower Broadway is touristy for a reason - it's fun, embrace it
• If you're traveling through, check out Loves RV stops - they're shockingly nice

Listen to the Full Episode

Want to hear the full story - including Peppermint Patty's college football predictions, Gremlin the cat's cross-country adventures, all the places we stayed, and way more detail than we could fit in this post?

Listen to Episode 10 of Marrying Your Passions: The DINK Travel and Adventure Podcast

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We release new episodes every other Wednesday, covering travel destinations, road trip tips, honest reviews, and the real talk about making adventure a priority as a childfree couple.

Coming up next: Our Virgin Voyages cruise review - the adults-only experience, what's worth it, and why we've now sailed with them twice.

Related Episodes You Might Like:

• Episode 4: Grand Teton and Yellowstone
• Episode 5: Park City, Utah and Wyoming's National Parks
• Episode 6: From Lincoln to Branson - Midwest Road Trip Stops
• Episode 9: Living in Denver - An Interview with Crazy Love Africa AirBNB Hosts

Subscribe so you don't miss our next adventure. And if you're planning a trip to Chicago or Nashville, tag us on social media @marryingyourpassions - we'd love to see your adventures!

Nathan and Alicia are the hosts of Marrying Your Passions, a podcast for DINKs (Dual Income, No Kids) who refuse to wait for "someday" to live their best lives. With 40+ marathons, three timeshares, and a dog who predicts college football games, they're proof that you can make adventure part of everyday life - even with full-time jobs and a dog who travels better than most people.