Explore the Heart of the USA on Route 66

Fly into Chicago’s O’Hare International Airport (ORD) or Midway International Airport (MDW), and drive your rental car to the official "Begin" sign for Route 66, which lies on East Adams Street, west of the intersection with South Michigan Avenue. For commemorative photos, however, check out the more artistic sign, complete with colorful map, placed in a small fenced park at Adams and Wabash streets. Before you hop on the road, make the most of Chicago by visiting the “Cloud Gate” sculpture, more commonly known as “The Bean.” This public sculpture is the centerpiece of Millennium Park. Take a Chicago architecture tour by boat to see some of the city's major architectural landmarks and enjoy the iconic skyline.

As you head to St. Louis, Missouri, make a pit stop at the Route 66 Association Hall of Fame and Museum in Pontiac, Illinois, about 161 kilometers southwest of Chicago. While there, check out the Route 66 Mural and other memorabilia.

Along the way to St. Louis, you'll find a host of famous motels, museums, drive-in restaurants and breakfast hot spots. It's impossible to miss the 192-meter-tall Gateway Arch; be sure to take a trip to the top of this stainless steel landmark — also known as the "Gateway to the West" — for breathtaking views of the city.

Get a taste of sports culture with a trip to Busch Stadium, home of the St. Louis Cardinals Major League Baseball team. Visit the Anheuser-Busch Brewery and take a tour. On the northern edge of the city, check out the Chain of Rocks Bridge, which crosses the Mississippi River. Part of Route 66 for several decades, the old bridge has since been turned into a landmark, bikeway and trail system on both sides of the river.

Your introduction to Oklahoma City is all about food. Pops 66 Soda Ranch, a landmark diner and gas station in Arcadia, serves 700 hundred different kinds of sodas, burgers, sandwiches, meatloaf and other comfort foods. Just look for the 21-meter-tall soda bottle out front. Or try one of the many barbecue spots in the area, including Jack's Bar-B-Q and Jigg's Smokehouse.

Digest at nearby Lake Hefner with a few hours of birdwatching and fishing. And for a little local culture, take a trip to The Womb art center. Founded by Flaming Lips frontman Wayne Coyne, this mural-splashed gallery features all kinds of psychedelic artwork and should provide plenty of conversation for the miles ahead.

Amarillo boasts a historic district listed on the U.S. National Register of Historic Places. The U.S. Route 66-Sixth Street Historic District is a 13-block development, home to several commercial buildings built in the Spanish Revival, Art Deco and Art Moderne styles and serves as a hub for socializing and entertainment. Meet and mingle with locals at the historic – and rumored to be haunted – Natatorium building, now converted into an antiques emporium.

Also in Amarillo, visit the famous Cadillac Ranch, an art installation that features several Cadillac car sculptures with their noses buried in the ground. Not to be outdone, VW Slug Bug Ranch in Conway, Texas, features five Volkswagen Beetles.

Before you get to Albuquerque, be sure to check out the Blue Hole, a bell-shaped blue pool east of Santa Rosa, New Mexico — a popular spot for scuba diving and relaxation. Once within the city limits, you can't miss the historic neon signs that light up Old Route 66. Albuquerque is home to an historic Old Town district and many great restaurants, shops and boutiques. Travelers making their way down Central Avenue marvel at the vintage signs adorning the storefronts. Tuck into traditional diner food at the whimsical 66 Diner on Central Avenue Northeast. Bring your appetite; this place serves up Fiesta Fries smothered in Texas chili and whole-milk milkshakes.

Littered with Route 66 signs, Holbrook, Arizona, is home to legendary motels and classic diners serving Tex-Mex style cuisine. It's easy to take a step back in time driving on this town's main strip. You can't miss the Wigwam Village Motel with 15 freestanding concrete teepees. Holbrook has earned a reputation for its quirky rock shops and dinosaur statues. Check out the brightly painted dinosaur statues in the downtown area before heading to Petrified Forest National Park. You'll need at least a day in this Painted Desert park, which features spectacular backcountry hikes and group activities, such as backpacking, ranger-guided tours and birdwatching.