Ultimate 7-Day Route 66 Road Trip Adventure Itinerary

Begin your day with a hearty breakfast at Lula Cafe, a local favorite. Then, immerse yourself in art at the Art Institute of Chicago with a fast-pass ticket.

After exploring the museum, take a break with a guided Chicago Favorite Foods Guided Walking Tour. Sample the diverse culinary offerings of the city. For a late lunch, visit Eataly Chicago for a taste of Italy in the heart of Chicago.

Spend a relaxing evening at Millennium Park, where you can admire the famous "Bean" and enjoy the serene atmosphere. For dinner, indulge in the innovative dishes at Girl & the Goat, a top-rated restaurant known for its bold flavors.

Grab a quick breakfast at Big Star, known for its tacos, before heading to the historic Wrigley Field. Take a guided tour and learn about the stadium's rich history.

For lunch, enjoy the vibrant atmosphere and delicious food at Xoco, a Rick Bayless restaurant specializing in Mexican cuisine. Afterward, explore the lively Navy Pier and its various attractions.

If the timing aligns, catch a thrilling Chicago Bulls Basketball Game at the United Center. For dinner, visit Pequod's Pizza for their famous caramelized crust pizza, a unique Chicago-style experience.

Start your day with a visit to the Taste of Chinatown Food Walking Tour, where you'll explore the vibrant neighborhood and enjoy a variety of Chinese delicacies. Alternatively, you can opt for a more traditional breakfast at Portillo's Hot Dogs.

After the tour, take a leisurely walk through the Magnificent Mile, Chicago's premier shopping destination. For lunch, try the award-winning burgers at Au Cheval.

Experience the city's nightlife with a Chicago Prohibition Speakeasies Bus Tour or Walking Tour. End the evening with a late dinner at Longman & Eagle, known for its upscale, yet relaxed, dining experience.

Delve into the city's past with a Chicago Gangsters and Ghosts Guided Walking Tour. Before the tour, enjoy a breakfast at Little Goat Diner, a casual spot with a creative menu.

After the tour, visit the Tribune Tower and the nearby Wrigley Building to admire their architectural significance. For lunch, head to Kuma's Corner for their legendary burgers.

Enjoy a relaxing evening at Soldier Field, home of the Chicago Bears. If there's no game, take a walk around the stadium and the surrounding park. For dinner, try the authentic barbecue at Smoque BBQ.

Begin your day with a visit to the Abraham Lincoln Presidential Library and Museum in Springfield, where you can immerse yourself in the life and times of the 16th President of the United States. Enjoy breakfast at a local diner, such as Cozy Dog Drive In, known for its iconic corn dogs.

After the museum, take a guided tour of the Dana-Thomas House, a stunning example of Frank Lloyd Wright's architecture. For lunch, indulge in the comfort food at Maldaner's Restaurant, a historic spot in downtown Springfield.

Explore the quaint downtown area and visit the Old State Capitol, where Lincoln served as a legislator. Enjoy a relaxed dinner at Head West Sub Stop, a popular sandwich shop known for its variety of subs and sides.

Start your day with a visit to the iconic Gateway Arch, where you can ride to the top for stunning views of the city and the Mississippi River. For breakfast, try the local favorite, Crown Candy Kitchen, known for its old-fashioned soda fountain and delicious sandwiches.

After the arch, explore the exhibits at the St. Louis Zoo, one of the top zoos in the country, with free admission. For lunch, head to Bogart's Smokehouse and savor some of the best barbecue in the city.

Conclude your trip with a visit to Anheuser-Busch Brewery for a tour of the historic brewery and a tasting of their famous beers. For a final dinner in St. Louis, enjoy the upscale comfort food at Brasserie by Niche.

Enjoy a leisurely breakfast at The Publican, known for its hearty, rustic fare. Take a morning walk through Lincoln Park & Zoo, one of the oldest and most beautiful zoos in the country.

Spend your final afternoon in Chicago at the 360 Chicago Observation Deck (Formerly John Hancock Observatory), using your Chicago 360 Chicago Observation Deck Skip-the-Line Ticket. Take in the panoramic views and reminisce about your journey.

For a memorable farewell dinner, dine at Alinea, a three-Michelin-star restaurant known for its innovative and artistic approach to cuisine. End the night with a walk along the Chicago River, taking in the city lights and reflecting on your Route 66 adventure.