Begin your Route 66 journey in Chicago, where you’ll kick off your first day with a visit to the Route 66 ceremonial start sign at Navy Pier. Snap a selfie or two with the sign before boarding a tour boat for a sightseeing cruise on Lake Michigan. You’ll spot some of Chicago’s historic buildings along the waterfront, many of which have become icons of American architecture. After your tour, take a public bus or ride share to Millennium Park. This beloved city greenspace is packed with public art, including the famous Cloud Gate sculpture, and adjacent Grant Park features Buckingham Fountain. While you’re in the area, take time to wander the Art Institute of Chicago to admire some of the world’s most famous masterworks in one of the USA’s oldest art museums. If you worked up your appetite, try Cindy’s Rooftop for lunch (reservations recommended). Located on the 13th floor of the Chicago Athletic Association hotel, it’s the perfect spot to linger over craft cocktails and oysters with panoramic views of the parks and Lake Michigan. After lunch, spend the afternoon exploring Chicago’s vibrant Chinatown. Admire the intricate carvings that adorn the Nine Dragon Wall, then take a quick walk to Chinatown Square, where the Chinese in America Mural and bronze zodiac statues pay homage to Chicago’s diverse cultural heritages. Find treasures in Chinatown Square’s shops, teahouses and eateries, from local art to fresh-baked red bean buns and handcrafted boba tea. Be sure to save room for dinner at Alinea, a two-star MICHELIN restaurant in the Lincoln Park neighborhood. Opt for The Kitchen Table or Gallery experience for an intimate tour of the restaurant’s modernist tasting menus, or reserve The Salon experience for a more streamlined (but equally indulgent) night of fine dining. If you’re in the mood for one more cocktail before the night ends, take a taxi or rideshare over to the Streeterville Neighborhood for a rooftop nightcap at Streeterville Social.

Kick off your second day in Chicago with brunch at Lula Cafe, a bright and sunny spot in the hip Logan Square neighborhood. Take a taxi or rideshare or catch a public bus over to Lincoln Park, the city’s biggest public green space. Once in the park, there’s plenty to see and do: Savor Lake Michigan views along waterfront walking and biking trails, spot songbirds and waterfalls near the Alfred Caldwell Lily Pool, and let little ones swing and slide at the Sunshine Playscape. Two museums (the Chicago History Museum and Peggy Notebaert Nature Museum), the free Lincoln Park Zoo and verdant Lincoln Park Conservatory round out the offerings. Get immersed in Chicago’s rich sports history at Wrigley Field, a short bus or taxi ride north of the park. From March through September, you can grab tickets to a Chicago Cubs baseball game for a classic gameday experience. During the off-season, sign up for a behind-the-scenes tour for a guided excursion that takes you from the dugout to the press box with plenty of trivia and history in between. Cap off the day with a meal at Boka, a MICHELIN-starred eatery serving up contemporary American cuisine. Order off the a-la-carte menu to enjoy signature plates like brown butter roasted scallops and braised asparagus salad, or opt for the eight-course tasting menu with a wine or non-alcoholic beverage pairing to try it all. A 15-minute ride on the Red Line train will take you from Wrigley Field to the restaurant.

After arriving in Pontiac, immerse yourself in the Mother Road’s nostalgic history. This welcoming community is renowned for its vibrant outdoor art scene, most notably the Murals on Main Street. Follow the painted footprints on the downtown sidewalks for a self-guided walking tour to spot over 20 hand-painted murals that illustrate the area’s political, commercial and cultural history. Step inside the historic fire station, home to the Illinois Route 66 Hall of Fame & Museum, to browse thousands of vintage license plates and retro advertising signs. Upstairs, you can learn about life on the open road by peering inside the actual 1972 Volkswagen van owned by iconic Route 66 artist Bob Waldmire. Stop by Edinger’s Filling Station for lunch. Located right on the historic courthouse square, this nostalgic, service-station-themed diner is a favorite local spot for a juicy pork tenderloin sandwich, homemade chicken pot pie and a slice of famous strawberry rhubarb pie before you resume your journey. Spend the rest of your afternoon exploring Pontiac’s swinging pedestrian bridges, which span the Vermilion River and offer peaceful views of the surrounding parks. Before hitting the road again, tour the Pontiac-Oakland Automobile Museum for a close-up look at a stunning collection of antique cars, vintage gas pumps and rare automotive artifacts.

Illinois‘ capital city is the perfect next stop on your journey through U.S. history. President Abraham Lincoln lived here for much of his life, and the city preserves several historic sites related to his life and work. As you approach Springfield on Interstate 55, take a short detour to the town of Lincoln to snap a photo with the World’s Largest Railsplitter Covered Wagon. Once you’ve arrived in Springfield, learn more about the legacy of the USA’s 16th president with a visit to Lincoln Home National Historic Site. This memorial preserves the home where the Lincoln family lived until they moved into the White House in 1861. Take a guided tour of the home to see period-accurate furnishings, then explore the four surrounding blocks for more historical exhibits on Lincoln’s early life and political career. Continue your journey through Lincoln’s life at the Abraham Lincoln Presidential Library and Museum before paying respects in his final resting place at the Lincoln Tomb State Historic Site. For lunch, stop at a Route 66 classic. The Cozy Dog Drive In has been serving up its signature cozy dog (a hot dog frank on a stick, battered and deep-fried) since they were invented here in 1949. Spend the afternoon exploring the open-air Illinois Route 66 Experience at the Illinois State Fairgrounds. A larger-than-life collection of neon signs recreates what the route may have looked like as it was driven by travelers in its heyday. Take a drive through town to spot its three Muffler Men. These large, colorful statues were originally built to advertise businesses along Route 66; today, they offer a glimpse into quirky road trip culture of the mid-20th century. See the Southeast Spartan on Ash Street, the Lauterbach Tire Muffler Man on Wabash Avenue and Big Ron on Toronto Road. When night falls, head to the Route 66 Drive-In Theater to watch a movie from your car. With several showings during the summer months, this is one of only a few dozen drive-in movie theaters still operating in the USA.

As you drive across the Mississippi River and enter St. Louis, make a stop at Chain of Rocks Park to take a walk across the Old Chain of Rocks Bridge. Once traveled by cars crossing into Missouri from Illinois on Route 66, today the bridge is preserved as a historic landmark and open only to pedestrians and cyclists. Take in views of the mighty Mississippi River below and the St. Louis skyline to the south. You might even be able to spot your next stop: Gateway Arch National Park. Drive a half hour south to reach St. Louis’ most iconic landmark, which sits on over 35 hectares of parklands along the Mississippi River. Take a tram ride to the top of the arch for panoramic views of the city. While tickets are available at the park’s entrance, they often sell out, so it’s a good idea to purchase tickets online in advance. Back on the ground, explore historical exhibits at the free Museum under the Gateway Arch. You’ll find several great options for lunch within a short drive of the Arch; St. Louis’ renowned Pappy’s Smokehouse serves up tender barbecue with a range of savory sauces, while Chili Mac’s Diner offers retro ambiance and Midwestern chili plates on weekdays. After lunch, spend some time enjoying Forest Park, a sprawling green space packed with beautiful landscapes and hands-on attractions. The Saint Louis Art Museum, Saint Louis Zoo and Missouri History Museum are fun and educational stops for all ages – and they offer free admission. Kids (and kids at heart) can’t miss a chance to explore the City Museum downtown. One of the city’s most unique attractions, this hands-on attraction invites you to climb, slide and swing your way through whimsical sculptures in a former shoe factory. For adult travelers, the Anheuser-Busch Brewery gives you a backstage look at how Budweiser beer is made. After a day of exploration, grab a late night bite at The Village Bar, a St. Louis-area institution since 1948. With classic dive bar ambiance, local beer and budget-friendly burgers, this hangout in nearby Des Peres is perfect for a relaxed night out. If your journey ends here, spend the night at a hotel or vacation rental nearby before catching your flight home at St. Louis Lambert International Airport (STL). If you’re itching for more adventure on the open road, the rest of Route 66 awaits. Continue your trip through Missouri or all the way to Santa Monica, California, stopping in charming cities and towns all along the way.