There’s something deeply satisfying about a road trip that starts in a large city and ends somewhere quiet enough to hear the wind move through trees. Driving from Chicago to Jonesburg, Missouri does exactly that. The total drive can be approximately five and a half to six hours if you don’t linger, but this is not a trip to rush. The goal is Whispering Pines Treehouses, a sought-after, luxurious hideaway tucked into nature.
Leaving Chicago, the drive settles quickly on Highway I-55 South, where the skyline fades and Illinois open up. One of the first worthwhile stops is Pontiac, a small town that fully embraces its Route 66 heritage. The Route 66 Hall of Fame and the vibrant murals scattered throughout downtown are quick to explore but full of personality. It’s the kind of place that reminds you road trips used to be about curiosity, not just destinations.
Springfield, about three hours into the drive, is the heart of the trip. This is Lincoln country, and the Abraham Lincoln Presidential Library and Museum is genuinely engaging, even for people who usually skim history plaques. A short walk through the Lincoln Home National Historic Site adds a quiet, reflective pause before getting back on the road. If timing lines up with lunch, D’Arcy’s Pint is non-negotiable. Their legendary horseshoe sandwich is indulgent, messy, yet the perfect road-trip fuel.
From Springfield, the drive to St. Louis takes about an hour and forty-five minutes, and the Mississippi River crossing signals a shift in energy. If you want a quick detour, the old Chain of Rocks Bridge offers a unique stretch-your-legs moment with big views and Route 66 nostalgia. In St. Louis itself, picking just one highlight keeps things manageable…either a ride to the top of the Gateway Arch or a slow wander through Forest Park… one of the best urban parks in the country. Did you know…both the St. Louis Science Center and the St. Louis Zoo…are free to the public? However, my personal recommendation….something I raised my four children on…the reward of ice cream at the famous Ted Drewes on Route 66 is a must for custard-lovers!!!
St. Louis is also where you eat well or regret your choices. Pappy’s Smokehouse lives up to its reputation, serving Memphis-style barbecue that’s smoky, tender, and worth the wait. If the line feels excessive, Salt+Smoke is a solid backup with multiple locations and consistently excellent food. This is the last major city stop before the landscape starts to quiet down.
The final stretch west on Highway I-70 to Jonesburg takes about an hour and feels like an exhale. Cornfields replace traffic, exits thin out, and the pace naturally slows. Arriving in Jonesburg, you will see country life as well as four-wheelers driving on the roadways! Whispering Pines Treehouses after a full day on the road feels earned, comparing the hum of Chicago to the calm of the woods is striking. It’s the kind of trip where the journey adds depth to the destination, and by the time you settle into your treehouse and soak in a private hot tub, the outside world already feels far away.
Our custom-built treehouses not only offer private hot tubs, but also private hiking trails marked with blazes, making the trails easy to follow. Each treehouse has a complete kitchen, large picture windows for bird watching, king-size bed, soaking luxury bathtub with a dual rainfall shower head, washing machine/dryer as well as a firepit and gas grill. It’s our desire to provide a place to disconnect from the busyness of everyday life and invest in yourself and your partner while surrounded by nature.
We invite you to stay with us and make memories to last a lifetime!
