Chicago Chop House is a classic steakhouse set inside a beautifully restored 120-year-old brownstone, decorated with photos of local celebrities and longtime regulars. You’ll find hand-cut USDA Prime steaks, fresh seafood, and classic sides that are perfect for sharing at the table. Start with the baked truffle burrata or steak tartare, then dig into a bone-in ribeye or dry-aged filet mignon as you kick off your Route 66 adventure. Save room for dessert, the Godiva lava cake is purely indulgent.

VELE offers an upscale dining experience with a menu focused on seafood, steaks, and house-made pasta, making it a standout stop near Route 66. Steak lovers will want the aged filet, topped with rich beef bordelaise, Boursin cheese, creamy horseradish, and a cherry balsamic reduction. Add the sherry mushrooms and garlic mashed potatoes for the full experience. Start with eggplant bruschetta and finish with the spiced pear cheesecake, complete with pear compote and pear liqueur.

Since 1960, The Big Texan Steak Ranch has been dishing out Texas-sized bravado along Route 66. Hungry for fame? Tackle the legendary 72-ounce steak challenge. Finish it in an hour, and your meal is free, bragging rights included. After cheering on the brave, roam Amarillo’s largest gift shop and grab some steak seasoning for your own kitchen adventures. Then toast your visit at the brewery and settle in for the night at the motel or RV Ranch.

In Cuba, Missouri, this beloved spot brings one-of-a-kind barbecue, and yes, steaks too, to historic Route 66. Kick things off with the famous Redneck Nachos, piled high with pulled pork, cheese, onions, and jalapeños over crispy chips. Go classic with a pork steak dinner or dive into smoky brisket. Whatever you choose, don’t skip the sides, the mustard potato salad and poppy seed coleslaw are road-trip legends.

Looking for steak while passing through Kansas? Van’s Steakhouse in Baxter Springs is a local hotspot that’s family owned and big on comfort-food classics. Grab a seat, or a saddle, yes, the bar really does have real saddles, and dig into flavorful steaks and their iconic chicken-fried steak. Save room for dessert, because the homemade cream pies are a can’t-miss finish to this down-home Route 66 stop.

You can’t miss Cattlemen’s Steakhouse, just look for the bright red neon sign glowing in Oklahoma City’s historic Stockyards. This Route 66 favorite serves up flavorful T-bone steaks, along with boneless rib eyes and classic New York strips cooked just right. Want something lighter? Start with a cup of their famous steak soup. Finish your meal on a sweet note with the mouthwatering strawberry shortcake, a longtime crowd pleaser.

Del’s Restaurant is a Tucumcari spot that feels right at home on any Route 66 road trip. This classic diner serves up hearty American comfort food in a relaxed, no-frills setting that’s perfect after a day on the road. Steak is on the menu alongside other familiar favorites, and the friendly service and old-school vibe make it an easy, welcoming stop while passing through town.

You’ll need to take a short detour to Tucson for steak while cruising through Arizona, but Silver Saddle Steakhouse is absolutely worth the drive. This family-owned, rustic local gem has been serving the community for decades, cooking steaks over a smoky mesquite wood fire that adds unbeatable flavor. Dig into a perfectly aged porterhouse or classic T-bone, and don’t overlook the prime rib served with creamy horseradish.

Indulge in a uniquely crave-worthy BBQ experience at Rusty Bull Roadhouse, where classic tradition meets comforting home cooking. Juicy Harris Ranch meats and house-made signature sauces are crafted to seriously impress steak lovers. It’s only a 20-minute detour from the Route 66 corridor to Apple Valley, and absolutely worth the drive. Save room for dessert, the funnel cake fries are fried perfection, and the mason jar sundae with Ghirardelli brownie and vanilla ice cream is a must.