One of the first highways in the American road system, Route 66 completely changed the way people approached travel. Route 66 was, and continues to be, much more than a slab of pavement that connects Chicago and Santa Monica. It's the opportunity to experience parts of America that are trapped in time. And most importantly, to drive Route 66 is to be free.

Go ahead and let your hair down and strap on your seatbelt. Make your road trip unforgettable by immersing yourself in the unique cities, natural wonders, and tasty eats found along the way.

A Few Road trip Tips:

Before you get started, keep the Golden Rules of Road tripping in mind.

1. Enjoy the Ride. “Are we there yet?" and "How much longer?” are negative phrases that have no place in your car. Start a “swear jar” and use the money donated by Negative Nancy to take a spontaneous excursion along the way.
2. Plan Ahead...But Leave Room for Sponteneity. Create a list of can’t-miss sights & activities, but don’t have an excel spreadsheet outlining every hour. Live in the moment!
3. Don’t Say Why, Ask Why Not! New food, why not!? Bungee jumping, why not?! Asking this question can only make your trip more interesting!
4. Chat Up the Locals. When you stop to pump gas, grab food, or just take a break to stretch your legs, take a moment to chat up the locals. Before you get back in the car, ask around and see if there's anything worth checking out while you're there. Don't know where to start? We put together a guide for chatting with locals.

Kick Things Off in the Windy City

Chicago is much more than your road trip launchpad. Your trip starts with the very first mile. Grab a slice of deep dish and head to the 95th floor at John Hancock’s lounge - martini’s all around! Take a stroll along the river and then hit the hay early to get some rest before the long days of driving to come.
Must Eat: Lou Malnati's Pizzeria, The Purple Pig
Must See: The 'Bean' at Millennium Park,
Art Institute of Chicago, Chicago Riverwalk

Mighty Midwest

As you wind from Chicago through the rest of Illinois, you’ll find little pieces of the 1920’s preserved in all of their retro glory. Stop in Pontiac, Illinois and visit the Route 66 Museum to learn about the travelers that came before you. Not to mention, Pontiac itself is pretty adorable and a good place to stop and stretch your legs. Look out for Abraham Lincoln-inspired attractions on the rest of your trip through Illinois.

Once you reach St. Louis, it's time for a reward. Ted Drewes Frozen Custard has been satisfying road trip sweet tooths from the beginning. Visit the famous Gateway Arch, and, if the season is right, catch a Cardinals game to revel in America's favorite pasttime.
Must Eat: Hendel's, Hi-Pointe Drive-In
Must See: Gateway Arch, Anheuser-Busch Brewery, City Museum

Southwest

As you enter Oklahoma you’ll know you’re officially in the Southwest. Get comfortable - over 400 miles of Route 66 run through Oklahoma, making this the longest stretch of the trip. But never fear! You can break it up by stopping in a few retro Route 66 motels and vintage gas stations. Be sure to spend plenty of time in Oklahoma City, touring the memorial for the Oklahoma City Bombing victims, and stopping in Bricktown where you'll find a vibrant restaraunt district with cafes and night clubs to explore.
Must Eat: Sunnyside Diner, Cheever's Cafe
Must See: Oklahoma City National Memorial and Museum, Bricktown, National Cowboy & Western Heritage Museum

When you hit the road again, red dust and Native American culture will surround you as you head into good ‘ol Amarillo, Texas. In Amarillo you absolutely have to stop by Amarillo Blvd. You won’t have a hard time finding a gentleman hoping to teach you how to two-step, and watch the sunset over that Amarillo sky blasting country music for your road neighbors to hear.

Wild West

No matter how many photos you’ve seen, the Grand Canyon is a wonder that can only be truly appreciated in person. Stretch your legs and take in the majesty of Mother Nature. Northern Arizona has a ton of outdoor goodies to explore, so take your time breathing that unfiltered air and shaking off the road.
Must Eat: El Tovar, Arizona Room
Must See: The Grand Canyon - particularly South Kaibab Trail and the Grand Canyon Skywalk.

Leaving behind natural wonders, it's time to hit up one of the greatest manmade marvels of the West. That’s right, it's Vegas baby! The iconic “sin city” is a hub of entertainment, glitz, and debauchery in the center of the desert. Visiting the city after trekking through the Grand Canyon is guaranteed to give you cultural whiplash - in the best way.
Must Eat: Ferraro's, Other Mama, Lotus of Siam
Must See: Vegas Strip!!

West Coast, Best Coast

Wrap up your adventures up in sunny southern California. You, conqueror of canyons, explorer of cities, American wanderer, deserve to enjoy all that Santa Monica has to offer. Splurge on a nice hotel along the boardwalk and hit the beach for some well-earned relaxation. Go window shopping on Rodeo Drive and keep an eye out for stars in Hollywood. But most importantly - reminisce on the trip you'll be talking about for the rest of your life.
Must Eat: Blue Plate Oysterette, The Bungalow, Fritto Misto
Must See: Santa Monica Pier, Abbot Kinney Boulevard, Third Street Promenade