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Ultimate 18-Day Route 66 Adventure Itinerary
Last updated: 2024 Jun 14Iconic Beginnings in the Windy City
Morning
Begin your Route 66 journey with a hearty breakfast at Lou Mitchell's, a classic diner known for its delicious pancakes. Afterward, take a morning stroll and visit the start of Route 66 at the Beginning of Route 66 Sign.
Afternoon
Immerse yourself in the vibrant culture of Chicago with a visit to the Art Institute of Chicago. Afterward, enjoy a famous Chicago-style hot dog at Portillo's for lunch.
Evening
Experience the dazzling Chicago skyline by night on the Navy Pier Centennial Wheel. For dinner, indulge in the exquisite seafood at The Signature Room at the 95th.
Bedtime
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Historic Landmarks and River Cruises
Morning
Start your day with a guided tour of the stunning Chicago Architecture River Cruise. Afterward, grab a coffee at Garrett Popcorn Shops and enjoy a morning snack.
Afternoon
Explore the iconic Willis Tower (Sears Tower) and step out onto the Skydeck for breathtaking views. For lunch, savor the flavors of Giordano's Pizza, famous for its deep-dish pizza.
Evening
Wind down with a leisurely walk through the serene Millennium Park. Dine at The Gage, known for its rustic, yet refined atmosphere and cuisine.
Bedtime
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Gateway to the West
Morning
Start your day with a visit to the iconic Gateway Arch and take a ride to the top for panoramic views. Enjoy breakfast at Bogart's Smokehouse, known for its mouthwatering barbecue.
Afternoon
Immerse yourself in nature at the Missouri Botanical Garden, also known as Shaw's Garden. For lunch, visit Pappy's Smokehouse for some of the best ribs in town.
Evening
Conclude your day with a visit to the interactive City Museum, an eclectic mix of children's playground, funhouse, and architectural marvel. Enjoy dinner at The Hilltop Inn, a local favorite known for its cozy atmosphere and delicious fare.
Bedtime
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Cultural Delights and Riverfront Relaxation
Morning
Begin with a visit to the St. Louis Zoo, a top-rated attraction with a diverse range of animals. Enjoy breakfast at Crown Candy Kitchen, a St. Louis institution known for its sweet treats and hearty sandwiches.
Afternoon
Explore the St. Louis Science Center and the nearby Forest Park. For lunch, head to Blueberry Hill, a vibrant restaurant with a unique collection of pop culture memorabilia.
Evening
Wind down with a leisurely stroll along the Laclede's Landing, a historic district with charming cobblestone streets. Dine at The Schlafly Tap Room, a local brewery and restaurant known for its craft beers and pub fare.
Bedtime
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A Day of Lincoln and Historic Sites
Morning
Start your day with a visit to the Abraham Lincoln Presidential Library and Museum, where you can immerse yourself in the life and times of the 16th President. Enjoy a classic American breakfast at The Cozy Dog Drive In, home of the famous "cozy dog."
Afternoon
Explore the historic Old State Capitol, where Lincoln delivered his famous "House Divided" speech. For lunch, visit D'Arcy's Pint, a local favorite known for its Irish hospitality and cuisine.
Evening
Conclude your day with a visit to the serene Lincoln's Tomb, the final resting place of Abraham Lincoln. Enjoy dinner at Maldaner's Restaurant, a historic spot known for its elegant ambiance and contemporary American cuisine.
Bedtime
Find amazing hotels in Springfield, Illinois.
Scenic Drives and Historic Towns
Morning
Start with a scenic drive on the Great River Road, offering picturesque views of the Mississippi River. Grab breakfast at Jimmy's Bar, a local spot known for its laid-back atmosphere and hearty meals.
Afternoon
Explore the charming town of Alton, Illinois, known for its historic architecture and antique shops. For lunch, visit My Just Desserts, a cozy cafe famous for its homemade pies.
Evening
Wind down with a visit to the Cahokia Mounds State Historic Site, the largest pre-Columbian settlement north of Mexico. Dine at The Loading Dock, a unique restaurant with a waterfront setting and live music.
Bedtime
Find amazing hotels in Springfield, Illinois.
Prairies and Historic Homes
Morning
Begin with a visit to the Lincoln Home National Historic Site, where Abraham Lincoln and his family lived for 17 years. Enjoy breakfast at Fulgenzi's Pizza & Pasta, a local favorite known for its hearty Italian dishes.
Afternoon
Explore the Henson Robinson Zoo, a small, family-friendly zoo with a variety of animals. For lunch, visit The Corner Pub and Grill for a casual dining experience with a diverse menu.
Evening
Conclude your day with a visit to the Knight's Action Park, where you can enjoy water rides and other attractions. Dine at Saputo's, a classic Italian restaurant known for its warm hospitality and delicious food.
Bedtime
Find amazing hotels in Springfield, Illinois.
Trails and Nature
Morning
Start your day with a visit to the Washington Park, a picturesque spot for a morning walk. Enjoy breakfast at Lulu's Laundromat, a unique cafe with a retro vibe and delicious coffee.
Afternoon
Explore the Sangchris Lake State Park, where you can hike, fish, or simply enjoy the natural beauty. For lunch, visit Head West Sub Stop for a satisfying sub sandwich.
Evening
Wind down with a visit to the Kickapoo Creek Park, a peaceful park with walking trails and a lake. Dine at Boone's Saloon, a laid-back restaurant with a menu of American classics.
Bedtime
Find amazing hotels in Springfield, Illinois.
Museums and History
Morning
Start with a visit to the Illinois State Museum, where you can explore the natural and cultural history of the state. Grab a coffee and pastry at The Feed Store, a charming cafe with a rustic ambiance.
Afternoon
Explore the Dana-Thomas House, a stunning example of Frank Lloyd Wright's architecture. For lunch, visit The Alamo, a local spot known for its Tex-Mex cuisine and lively atmosphere.
Evening
Conclude your day with a visit to the Edwards Place Historic Home, a beautifully preserved historic home. Dine at Maldaner's Restaurant, a local favorite with a menu of contemporary American cuisine.
Bedtime
Find amazing hotels in Springfield, Illinois.
A Day of Lincoln and Historic Sites
Morning
Start your day with a visit to the Abraham Lincoln Presidential Library and Museum, where you can immerse yourself in the life and times of the 16th President. Enjoy a classic American breakfast at The Cozy Dog Drive In, home of the famous "cozy dog."
Afternoon
Explore the historic Old State Capitol, where Lincoln delivered his famous "House Divided" speech. For lunch, visit D'Arcy's Pint, a local favorite known for its Irish hospitality and cuisine.
Evening
Conclude your day with a visit to the serene Lincoln's Tomb, the final resting place of Abraham Lincoln. Enjoy dinner at Maldaner's Restaurant, a historic spot known for its elegant ambiance and contemporary American cuisine.
Bedtime
Find amazing hotels in Springfield, Illinois.
Scenic Drives and Historic Towns
Morning
Start with a scenic drive on the Great River Road, offering picturesque views of the Mississippi River. Grab breakfast at Jimmy's Bar, a local spot known for its laid-back atmosphere and hearty meals.
Afternoon
Explore the charming town of Alton, Illinois, known for its historic architecture and antique shops. For lunch, visit My Just Desserts, a cozy cafe famous for its homemade pies.
Evening
Wind down with a visit to the Cahokia Mounds State Historic Site, the largest pre-Columbian settlement north of Mexico. Dine at The Loading Dock, a unique restaurant with a waterfront setting and live music.
Bedtime
Find amazing hotels in Springfield, Illinois.
Prairies and Historic Homes
Morning
Begin with a visit to the Lincoln Home National Historic Site, where Abraham Lincoln and his family lived for 17 years. Enjoy breakfast at Fulgenzi's Pizza & Pasta, a local favorite known for its hearty Italian dishes.
Afternoon
Explore the Henson Robinson Zoo, a small, family-friendly zoo with a variety of animals. For lunch, visit The Corner Pub and Grill for a casual dining experience with a diverse menu.
Evening
Conclude your day with a visit to the Knight's Action Park, where you can enjoy water rides and other attractions. Dine at Saputo's, a classic Italian restaurant known for its warm hospitality and delicious food.
Bedtime
Find amazing hotels in Springfield, Illinois.
Trails and Nature
Morning
Start your day with a visit to the Washington Park, a picturesque spot for a morning walk. Enjoy breakfast at Lulu's Laundromat, a unique cafe with a retro vibe and delicious coffee.
Afternoon
Explore the Sangchris Lake State Park, where you can hike, fish, or simply enjoy the natural beauty. For lunch, visit Head West Sub Stop for a satisfying sub sandwich.
Evening
Wind down with a visit to the Kickapoo Creek Park, a peaceful park with walking trails and a lake. Dine at Boone's Saloon, a laid-back restaurant with a menu of American classics.
Bedtime
Find amazing hotels in Springfield, Illinois.
Museums and History
Morning
Start with a visit to the Illinois State Museum, where you can explore the natural and cultural history of the state. Grab a coffee and pastry at The Feed Store, a charming cafe with a rustic ambiance.
Afternoon
Explore the Dana-Thomas House, a stunning example of Frank Lloyd Wright's architecture. For lunch, visit The Alamo, a local spot known for its Tex-Mex cuisine and lively atmosphere.
Evening
Conclude your day with a visit to the Edwards Place Historic Home, a beautifully preserved historic home. Dine at Maldaner's Restaurant, a local favorite with a menu of contemporary American cuisine.
Bedtime
Find amazing hotels in Springfield, Illinois.
A Day of Lincoln and Historic Sites
Morning
Start your day with a visit to the Abraham Lincoln Presidential Library and Museum, where you can immerse yourself in the life and times of the 16th President. Enjoy a classic American breakfast at The Cozy Dog Drive In, home of the famous "cozy dog."
Afternoon
Explore the historic Old State Capitol, where Lincoln delivered his famous "House Divided" speech. For lunch, visit D'Arcy's Pint, a local favorite known for its Irish hospitality and cuisine.
Evening
Conclude your day with a visit to the serene Lincoln's Tomb, the final resting place of Abraham Lincoln. Enjoy dinner at Maldaner's Restaurant, a historic spot known for its elegant ambiance and contemporary American cuisine.
Bedtime
Find amazing hotels in Springfield, Illinois.
Scenic Drives and Historic Towns
Morning
Start with a scenic drive on the Great River Road, offering picturesque views of the Mississippi River. Grab breakfast at Jimmy's Bar, a local spot known for its laid-back atmosphere and hearty meals.
Afternoon
Explore the charming town of Alton, Illinois, known for its historic architecture and antique shops. For lunch, visit My Just Desserts, a cozy cafe famous for its homemade pies.
Evening
Wind down with a visit to the Cahokia Mounds State Historic Site, the largest pre-Columbian settlement north of Mexico. Dine at The Loading Dock, a unique restaurant with a waterfront setting and live music.
Bedtime
Find amazing hotels in Springfield, Illinois.
Prairies and Historic Homes
Morning
Begin with a visit to the Lincoln Home National Historic Site, where Abraham Lincoln and his family lived for 17 years. Enjoy breakfast at Fulgenzi's Pizza & Pasta, a local favorite known for its hearty Italian dishes.
Afternoon
Explore the Henson Robinson Zoo, a small, family-friendly zoo with a variety of animals. For lunch, visit The Corner Pub and Grill for a casual dining experience with a diverse menu.
Evening
Conclude your day with a visit to the Knight's Action Park, where you can enjoy water rides and other attractions. Dine at Saputo's, a classic Italian restaurant known for its warm hospitality and delicious food.
Bedtime
Find amazing hotels in Springfield, Illinois.
Trails and Nature
Morning
Start your day with a visit to the Washington Park, a picturesque spot for a morning walk. Enjoy breakfast at Lulu's Laundromat, a unique cafe with a retro vibe and delicious coffee.
Afternoon
Explore the Sangchris Lake State Park, where you can hike, fish, or simply enjoy the natural beauty. For lunch, visit Head West Sub Stop for a satisfying sub sandwich.
Evening
Wind down with a visit to the Kickapoo Creek Park, a peaceful park with walking trails and a lake. Dine at Boone's Saloon, a laid-back restaurant with a menu of American classics.
Bedtime
Find amazing hotels in Springfield, Illinois.
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