Sit back, relax and enjoy these delectable dining destinations located just off The Mother Road along The First Hundred Miles. Sporting vintage ambiance, modern menus, Route 66 ephemera and artisan drinks, this collection of restaurants highlights both classic Route 66 eateries and exciting newer spots found along the legendary road trip destination.
Travelers cruising the Illinois stretch of the Mother Road have long made a stop at Dell Rhea’s Chicken Basket (645 Joliet Road I-55 & Route 83, Willowbrook), a roadside institution that has been serving hungry Route 66 motorists since the early 1940s. Originally opened as a combination service station and restaurant, the spot grew in popularity alongside the highway itself. Guests still come from near and far for the restaurant’s famous fried and roasted chicken, along with comforting favorites like corn fritters, baby back ribs, homemade mashed potatoes and an all-you-can-eat salad bar served in a charming country-style dining room.
A little further south, travelers can’t miss White Fence Farm (1376 Joliet Road, Romeoville), easily identified by the towering water tower marked with its iconic “WWF.” For more than 65 years, this longtime Route 66 favorite has been serving what it proudly calls “The World’s Greatest Chicken.” Their famous twice-cooked process, baked and then fried, creates a thin yet perfectly crispy crust that keeps fried chicken fans coming back. In keeping with the authentic farm theme, every meal is accompanied by classic sides such as coleslaw, cottage cheese, bean salad, pickled beets and your choice of potatoes.
In Crest Hill, Merichka’s (604 Theodore St., Crest Hill) continues a family-owned tradition that dates back to 1933. Known for its unique take on the po’boy sandwich made with fresh fried chicken instead of the traditional fillings, this classic supper club is also celebrated for its quality hand-cut meats and house-ground burgers. Inside, dark wood paneling, red-checkered tablecloths and a generous bar evoke the feel of a vintage Midwestern steakhouse, while the menu features steaks, seafood and the restaurant’s beloved Garlic Butterine that adds a signature flavor to nearly any dish.
Also in Lemont, Rosebud Lemont (12350 Derby Road, Lemont) offers an elegant stop for those craving classic Italian cuisine. Serving guests since 1976, the restaurant features a grand ballroom-style dining room that provides a refined setting for memorable meals. Guests seeking a more intimate experience can dine in the Sinatra Room, while the energetic bar hosts live music on weekends. With a menu rooted in centuries-old Italian recipes and several unique dining spaces, Rosebud Lemont accommodates everything from intimate dinner dates to large gatherings.
Mauve Cocktail Lounge (1146 W. Jefferson St., Shorewood) offers a stylish stop for travelers exploring the First Hundred Miles of Route 66. The lounge-style space features dramatic décor, velvet accents, chandeliers, and dim lighting that create an intimate and upscale atmosphere. Mauve is known for its creative craft cocktails, including an extensive martini selection and inventive drinks made with house ingredients and fresh flavors. The food menu centers on shareable small plates and elevated bar bites such as charcuterie boards, sliders, and other dishes designed for relaxed social dining, making it a perfect place to unwind after a day on the Mother Road.
For another taste of Italy nearby, travelers can visit La Dolce Vita per Tutti (16108 Illinois Route 59, Plainfield), a cozy neighborhood trattoria offering classic Italian comfort dishes. The welcoming atmosphere pairs perfectly with a menu filled with generous portions of traditional favorites such as lobster stuffed ravioli, chicken marsala, eggplant parmesan and linguine with clams. Guests often begin with appetizers like fried calamari or Italian sausage and peppers before finishing the meal with decadent desserts, making it a delightful stop for anyone looking to enjoy a little slice of the sweet life along the Route 66 corridor.
Mediterranean flavors take center stage at Pesciolino Osteria (25445 Pheasant Lane, Channahon), where chefs showcase the culinary traditions of Italy, Greece and the broader Mediterranean region. The menu highlights fresh seasonal fish and seafood, aged steaks, organically raised chicken and handcrafted pasta prepared with high-quality ingredients. Guests can pair their meal with signature cocktails or selections from the restaurant’s wine list while enjoying the intimate modern-casual dining space.
For a true retro roadside experience, travelers often pull over at Polk-A-Dot Drive-In (222 N. Front St., Braidwood). This lively 1950s-style diner is packed wall-to-wall with vintage memorabilia and lined outside with colorful fiberglass statues of pop culture icons like Elvis Presley and Betty Boop. Inside, black-and-white checkered floors, stainless steel accents and jukebox booths create a nostalgic setting where guests can enjoy drive-in classics such as burgers, malts and chili cheese fries. Outdoor picnic tables overlooking Old Route 66 offer the perfect place to soak in the atmosphere.
Further down the road in Dwight, Old Route 66 Family Restaurant (105 S. Old Route 66, Dwight) provides a welcoming stop for travelers looking for hearty home-cooked meals. The building’s exterior features a colorful Route 66 mural, while inside a real fire engine chassis has been creatively transformed into the cashier station. Known for generous portions and friendly service, the restaurant offers daily specials, homemade soups and desserts along with family-style options like “Chicken by the Bucket” and “Sides by the Pound.”
Finally, visitors to Pontiac can enjoy a classic roadside dining experience at Old Log Cabin Restaurant (18700 Historic U.S. 66, Pontiac). Welcoming guests from around the world, this longtime Route 66 establishment serves breakfast, lunch and dinner in a warm and friendly atmosphere. Known for its comforting home-style meals and made-from-scratch pies, the Old Log Cabin continues the tradition of hospitality that has made dining along the Mother Road such a memorable part of the journey.
