Explore the Historic Route 66 Start Sign: Your journey officially begins in Chicago, where you can take a photo with the iconic Start of Route 66 sign at the corner of Adams Street and Michigan Avenue.
Willis Tower Skydeck: If you’re an urban adventurer, take in the breathtaking views from one of Chicago’s most famous skyscrapers.
Route 66 Visitor Center: Located at the Chicago History Museum, it’s a great spot to pick up maps and souvenirs and learn about Route 66’s history.
Solo Dining at Classic Diners: Check out the Ed’s Diner or The Silver Palm for a true Route 66 experience with hearty diner fare.

The Joliet Area Historical Museum: Here, you’ll get a deep dive into the history of Route 66 and the city’s role in the motor age. The museum also showcases vintage artifacts, making it a great solo exploration spot.
Route 66 Welcome Sign: Snap a photo with the Route 66 sign at the intersection of Chicago Street and Route 66 Parkway—perfect for solo adventurers.
Joliet Prison: The old prison, now closed, offers a fascinating history. They sometimes offer tours or, if you're lucky, special events. It’s a slightly eerie but unique experience.

Gemini Giant: A must-see for anyone traveling Route 66, this giant roadside statue of a space-age astronaut is a classic and makes for a fun solo photo op.
Route 66 Food & Culture: Wilmington is a small town where you can enjoy the peaceful pace of the road, grab a bite at The Choo Choo Restaurant, and soak in the retro vibe.

Route 66 Museum: Pontiac is home to one of the best Route 66 museums in the country. It’s full of memorabilia, vintage signs, and exhibits about the people and places that made Route 66 iconic. A fantastic spot to wander around on your own.
Mural Walk: The city is covered in murals dedicated to Route 66 history. Take a solo walking tour through the murals to learn more about the historic significance of the route.

The McLean County Museum of History: Explore local history and its connection to Route 66 in this well-curated museum.
David Davis Mansion: Explore the historic mansion of Abraham Lincoln's friend, and enjoy the beautiful grounds. It’s a peaceful and educational stop for solo travelers who enjoy history.

Abraham Lincoln’s Tomb: While not directly related to Route 66, a visit to the Lincoln Tomb State Historic Site in Lincoln is a must for history buffs. Take some time to reflect in the tranquil surroundings.
The Route 66 Hall of Fame & Museum: This museum showcases Route 66 history, featuring artifacts from travelers and locals who helped shape the route.

Abraham Lincoln Presidential Library and Museum: Springfield is deeply tied to Lincoln’s legacy, and visiting the presidential library and museum is an essential stop for any solo traveler interested in American history.
Route 66 Roadside Attractions: Explore iconic Springfield landmarks like the Lincoln Home National Historic Site, Miller Park, and quirky roadside attractions such as the Cozy Dog Drive-In, known for inventing the corn dog!

Litchfield Route 66 Welcome Center: A fun stop with plenty of information on the history of Route 66. It's a welcoming place for solo travelers to stretch their legs and chat with fellow Route 66 enthusiasts.
Litchfield’s Famous Chain of Rocks Bridge: A scenic stop for a peaceful walk and photo ops, plus the historic bridge is a must-see for any Route 66 traveler.

Carlinville’s Historic Square: A perfect solo stop to explore the beautiful courthouse square and local shops. This is a peaceful, relaxing stop on your journey, ideal for reflection.
Belt’s Smokehouse: Enjoy a meal at this local gem, famous for its delicious smoked meats and perfect for solo dining.

Edwardsville Historic District: Wander around the quaint historic district and visit The Wildey Theatre, an old-time theater with films and events that might coincide with your visit.
Giant Route 66 Signs: Snap one last solo photo with one of the large Route 66 signs near Edwardsville before wrapping up your Illinois portion of the journey.

Stay at Budget Motels & Inns: There are many affordable options along the route, like old-school motels that still preserve the nostalgia of Route 66. Many even have great stories and histories attached to them.
Take Solo Photos: Whether it’s at the iconic Route 66 signs or quirky roadside attractions, you can always ask a friendly traveler to take your picture or use a timer to capture your solo adventure.
Solo Dining: Many towns along Route 66 have small diners that are perfect for solo travelers. Don’t miss out on local specialties like the famous Cozy Dog or a slice of classic Route 66 pie.

Wandering Souls