🌆 1. Begin Your Journey at the Route 66 Starting Point (Chicago)

  • 📍 E. Adams St. & Michigan Ave.

  • Snap a photo under the “Begin Route 66” sign, right in the heart of downtown Chicago. The sign is across from the Art Institute and near Millennium Park—urban exploration heaven.

  • Tip: Wander nearby Michigan Avenue, which blends historic architecture with modern urban life.

🧱 2. Explore the Historic Lou Mitchell’s Restaurant (Chicago)

  • 📍 565 W. Jackson Blvd.

  • An iconic Chicago diner that has served Route 66 travelers since 1923. Famous for its coffee, doughnut holes, and urban diner vibes.

  • Urban Edge: Located right by Union Station and surrounded by classic Chicago high-rises.

🎨 3. Street Art & Murals in Pilsen (Chicago)

  • 📍 Pilsen neighborhood, South Side

  • This artsy neighborhood offers an explosion of color and culture, with block after block of murals, galleries, and hip cafes. A true gem for urban explorers.

  • Must-see: The “Greetings from Chicago” mural, a vibrant and popular Instagram stop on Route 66.

🏙 4. Route 66 Attractions in Downtown Joliet

  • 📍 Joliet Area Historical Museum & Route 66 Welcome Center

  • Joliet blends small city charm with urban grit—see the Joliet Prison, hit the Old Joliet Iron Works Historic Site, and don’t miss the glowing Route 66 sign arch downtown.

  • Bonus: Catch a performance or peek inside the Rialto Square Theatre, a stunning old-school urban venue.

🏭 5. Explore the Old Chain of Rocks Bridge (Madison)

  • 📍 Southwestern Illinois, near the Missouri border

  • This bridge once carried Route 66 traffic across the Mississippi and is now a pedestrian/bike path. It’s got an eerie, abandoned feel that urban explorers love.

  • Urban Vibes: Crumbling remnants of history + riverfront views = explorer gold.

🏙 6. Abandoned and Retro Motels & Gas Stations (Various Towns)

  • 📍 McLean, Dwight, Odell, and more

  • Keep your eyes peeled for photogenic abandoned motels, rusted neon signs, and classic Sinclair stations. These are urban decay meets mid-century Americana.

  • Cool Stops:

    • Ambler-Becker Texaco Station (Dwight)

    • Odell Station

    • Sprague Super Service (Normal)

🧱 7. Visit the Illinois State Capitol & Historic Downtown (Springfield)

  • 📍 Springfield, IL

  • The Illinois State Capitol is visually striking, and Springfield’s downtown offers a blend of historic government buildings, art deco storefronts, and indie eateries.

  • Urban Explorer Bonus: The Old State Capitol, Lincoln sites, and historic neighborhoods with 1800s brick architecture.

📸 8. Snap a Selfie with the Giant “Muffler Men” (Atlanta & Wilmington)

  • 📍 Tall Paul (Atlanta), Gemini Giant (Wilmington)

  • These quirky, towering figures are Route 66 icons—and the kind of kitschy urban roadside art that make for unforgettable photos.

  • Urban appeal: There's something oddly magical about a huge statue rising from a tiny town square.

🚂 9. Trainspotting & Architecture at Union Station (Chicago)

  • 📍 225 S. Canal St., Chicago

  • This historic station is still active and features incredible Beaux-Arts architecture and cinematic history (yes, The Untouchables scene!). A classic urban explorer location.

  • Tip: Just a short walk from Lou Mitchell’s and the start of Route 66.

☕️ 10. Coffee, Craft Beer & Hidden Bars in Chicago

  • 📍 Logan Square, West Loop, and Fulton Market

  • These areas aren't on Route 66 per se, but they offer the gritty, rejuvenated warehouse vibes urban explorers love—murals, lofts, and hidden speakeasies.

  • Highlights:

    • The Aviary (cocktail lab)

    • Caffe Streets (hipster coffee)

    • Goose Island Brewery (original Chicago location)

🚶 11. Take the 66-Foot-Tall Route 66 Experience Walk (Litchfield)

  • 📍 Litchfield Museum & Route 66 Welcome Center

  • A walking tour of vintage signs and displays related to Illinois’ Route 66 history. Small town with urban-style mural flair.

🎭 12. Experience Live Music & Nightlife (Chicago & Springfield)

  • Catch jazz or blues at iconic Chicago venues like Buddy Guy’s Legends or The Green Mill, or explore local dive bars and music in Springfield’s downtown.

  • These venues have strong urban heritage vibes—gritty, real, and full of stories.

🎥 13. Film Locations Along the Route

  • Chicago is full of film locations, especially for urban scenes. Think The Dark Knight, Ferris Bueller, and Blues Brothers. Explore alleyways, bridges, and rooftops that look familiar—you’ve seen them on screen.

🚶‍♀️ Urban Explorer Tips:

  • Stay flexible: Many of the best finds aren’t on a map—keep your eyes open for ghost signs, street art, and hidden gems.

  • Walk cities & towns: Park and walk. Urban exploration is best done on foot.

  • Photography-ready: Bring your camera or phone with space for photo after photo.

  • Get curious: Talk to locals, especially in places like Joliet and Springfield—they’ll point you to places off the radar.