Drive Route 66 from Chicago Through Illinois — History, Hidden Gems & Wide-Open Prairie

Join Darley Newman on a Route 66 road trip through Illinois, starting at the Mother Road's Chicago starting point and heading south through some of the most iconic and surprising stops along this legendary American highway. From retro diners to a rare national prairie, this Illinois road trip delivers history, adventure, and a few scoops of ice cream along the way. What You'll Experience in This Episode: ✅ Route 66 Starting Point & Illinois Road Trip Overview — Learn the full Route 66 Illinois route, stretching from Lake Michigan in Chicago through Joliet, Bloomington, Springfield, and on to East St. Louis — 301 miles of Mother Road history. ✅ Gemini Giant & Launching Pad, Wilmington — Meet one of Route 66's most photographed fiberglass giants, a kitschy 1960s spaceman landmark celebrating America's space race era. ✅ Polka-Dot Drive-In, Braidwood — Step back into 1956 at this beloved retro drive-in featuring a 9-foot Elvis, the Blues Brothers, Marilyn Monroe, and a legendary Polka-Dot burger. ✅ Rialto Square Theatre, Joliet — Tour one of the most magnificent Vaudeville movie palaces in the United States, modeled after the Pantheon in Rome, with a crystal chandelier called "the Duchess" and a Hall of Mirrors inspired by Versailles. ✅ Rich and Creamy Ice Cream Stand, Joliet — End the day like a true Route 66 road tripper with a turtle sundae at this old-fashioned ice cream stand where the Blues Brothers dance on the roof. ✅ Midewin National Tallgrass Prairie — Discover one of Illinois' most surprising Route 66 roadside stops: the nation's first National Tallgrass Prairie, home to restored bison herds, over 20 miles of horseback riding trails, rare bird species, and WWII-era munitions bunkers from the former Joliet Army Ammunition Plant. ✅ Volunteer Vacation on Route 66 — Darley goes hands-on harvesting native seeds with The Nature Conservancy and the Midewin Tallgrass Prairie Alliance to help restore one of America's rarest ecosystems. ✅ Horseback Riding with Will County Trail Riders — Saddle up and ride the trails at Midewin, just an hour from Chicago, with locals who have watched the prairie transform before their eyes. 🗺️ Plan Your Illinois Route 66 Road Trip: 📍 Route 66 starting point: Lake Shore Drive, Chicago, Illinois 📍 Gemini Giant / Launching Pad — Wilmington, IL 📍 Polka-Dot Drive-In — Braidwood, IL 📍 Rialto Square Theatre — Joliet, IL 📍 Rich and Creamy — Joliet, IL 📍 Midewin National Tallgrass Prairie — Wilmington/Elwood, IL 📺 Watch "Travels with Darley: Illinois Route 66 & Midewin" on PBS & Streaming: https://www.darley-newman.com/travels-with-darley 🔔 Subscribe for More Travel & History Videos: https://darley.link/youtubesubscribe 🎧 Listen to the "Travels with Darley" Podcast: https://www.iheart.com/podcast/53-travels-with-darley-123513653/ 📲 Follow Darley for Exclusive Travel Content: Instagram: https://www.instagram.com/darleynewman/ Facebook: https://www.facebook.com/travelswithdarley TikTok: https://www.tiktok.com/@darleynewman Twitter (X): https://x.com/DarleyNewman