Amy Bizzarri - The Best Hits on Route 66: 100 Essential Stops on the Mother Road

Amy Bizzarri is a freelance writer with a focus on family adventures and outdoor fun. She has a keen interest in Chicago history and is the author of 111 Places in Chicago That You Must Not Miss and Discovering Vintage Chicago. Route 66 holds a special place in her heart, and you might just find her on the road, hiking the Petrified Forest, climbing the Amboy Crater, or diving into the Blue Hole of Santa Rosa.

Route 66 Official Starting Point and the Ledge of the Willis Tower Skydeck Chicago, IL

Lou Mitchells Restaurant and Bakery Chicago, IL

Dell Rheas Chicken Basket Willowbrook, IL

Car Racing Experience at the Route 66 Raceway Elwood, IL

Buffalo Roaming at Midewin National Tallgrass Prairie Wilmington, IL

Gemini Giant Wilmington, IL

Bob Waldmires 1972 VW Microbus at the Route 66 Association Hall of Fame and Museum Pontiac, IL

Funks Grove Pure Maple Sirup Shirley, IL

Auburn Brick Road Auburn, IL

Land of Lincoln Springfield, IL

Springfields Iconic Diners Springfield, IL

Docs Soda Fountain Girard, IL

Sky View Drive-In Litchfield, IL

Ariston Caf Litchfield, IL

Henrys Rabbit Ranch Stauton, IL

Worlds Largest Catsup Bottle Collinsville, IL

Cahokia Mounds State Historic Site Collinsville, IL

Luna Caf Granite City, IL

Chain of Rocks Bridge Granite City, IL /St. Louis, MO

ROUTE 66 OFFICIAL STARTING POINT AND THE LEDGE OF THE WILLIS TOWER SKYDECK

Your adventure of a lifetime begins here, in the midst of downtown Chicagos hustle and bustle. An official US 66 sign, mounted so that it faces westbound traffic, marks the Mother Roads starting point on East Adams Street, just west of its intersection with South Michigan Avenue.

Route 66, however, originally began on Jackson Boulevard at Michigan Avenue.

Early 1920s Chicago boasted one of the largest street railway systems in the world, but Jackson Street remained one of the few downtown boulevards without a streetcar line, making it the perfect pick for a new, transnational US highway. Officially named Route 66 on April 30, 1926, Jackson Boulevard became part of the Mother Road and began whisking generations of migrants and road-tripping vacationers westward. In 1955, however, the boulevard was transformed into a one-way street, and Adams Street at Michigan Avenue became the new launching point for US-66.

At 1,450 feet high1,730 feet if you include its twin antenna towersWillis Tower is the second tallest building in North America and the twelfth tallest building in the world. Completed in 1973, the former Sears Tower was built to house Sears, Roebuck & Co, once the largest retailer in the world. The towers thrilling observation deck, the Skydeck, is the highest in the United States. On a clear day, you can see up to 50 miles down Route 66; looking to the east you can see across Lake Michigan, all the way to Indiana and Michigan.

PIT STOP PHOTO OP

S nap a selfie in front of the official starting point sign on East Adams Street and then make your way skyward to the best place to kick off your Route 66 adventure: 1,353 feet in the sky above Jackson Boulevard.

Even the elevator ride up to the top of the tower is a thrill. The ride only takes about 60 seconds, and youll feel the pressure as you rise toward the clouds. On a windy day, youll also feel the sway: The tower is known to move about 8 inches at the top on remarkably Windy City days.

For the ultimate look at the road ahead, step upon the Ledge, a panel of four glass balconies extending 4 feet from the west-facing faade of the 103rd floor, and peer through the glass floor at Route 66, which lies 1,353 feet below. Though standing on the glass is enough to give even the bravest of souls a scare, these panels can bear 5 tons of weight, so you can count on not falling overor throughthe Ledge.

Route 66 Official Starting Point, East Adams Street, just west of its intersection with South Michigan Avenue, Chicago

Ledge of the Willis Tower Skydeck, 233 S. Wacker Dr., Chicago, IL; (312) 875-9447; theskydeck.com

LOU MITCHELLS RESTAURANT AND BAKERY

Lou Mitchells has been providing the fuela.k.a. the worlds best coffeefor Route 66 adventures since the highway first opened for business in 1926. As the first full-service restaurant and bakery youll encounter along West Jackson Boulevard, the first westbound tract of the Mother Road, it has long served as a place of beginnings, giving patrons the gas they need for the road trip of a lifetime... or just another day at the office.

If youre especially hungry for a hearty breakfast, the line outside this iconic Chicago diner seems to stretch down the route all the way to Santa Monica Pier. Dont let the mouthwatering smell of pancakes and maple syrup overcome you; keep your eyes peeled for the hostess who passes out doughnut holes and Milk Duds to waiting customers.

Though the city that surrounds it has grown tall with skyscrapers over the years, little has changed inside: The original wooden stools at the multisided counters are packed with coffee-sipping, newspaper-reading regulars; couples cozy up to the wooden two-seater booths; families share laughter over fluffy pancakes in the larger booths. The shiny silver toasters pop up slices of bread ripe for a generous spread of butter; the salty-sweet smell of bacon wafts through the air; servers swerve from table to table, gracefully balancing fresh-from-the-skillet omelets and steaming coffee pots.

Lou Mitchells has been a long-standing whistle stop on the campaign trails of many political hopefuls, and the eclectic clientele also makes it a prime source for popular opinion when media outlets want to know how tried-and-true Chicagoans really feel about an issue or a candidate. Sit at the counter, where you can best trade travel tips with both fellow Route 66 road trippers about to set off into the sunrise or just swinging into town from an east-to-west journey.

Most everything here is made in-house, daily, from the bismarcks to the Belgian malted waffles. The cinnamon twists are hand rolled and the OJ freshly squeezed from Florida oranges. Lou Mitchells serves uniquely double-yolked eggs, and you can order them any way youd like; the omelets here are big enough for two and available in 20-plus savory combinations. Even the orange marmaladewhich youll always find on the tableis prepared the old-fashioned way and canned in the kitchen. The soda jerk on staff still whips up chocolate phosphates and Chicago egg creams using the same recipes from the diners early days. If youre traveling with little ones, the Mitchell Mouse pancakea mouse-shaped pancake with whipped cream eyebrows and smile, Milk Dud eyes, and a maraschino cherry noseis always a delight. Lou Mitchells is the only diner in the world that always serves dessert after breakfast: a scoop of creamy vanilla ice cream to cleanse the palate.