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Ultimate Route 66 Road Trip from Los Angeles to Chicago Itinerary
Last updated: 2024 Jun 14Starting the Journey on the Mother Road
Morning
Begin your iconic Route 66 road trip by picking up your rental car. Before hitting the road, savor a classic breakfast at the famous Roscoe's House of Chicken and Waffles.
Afternoon
Head to the historic Santa Monica Pier and take a leisurely walk along the boardwalk. Enjoy a seafood lunch at The Lobster, overlooking the Pacific Ocean.
Evening
Explore the vibrant nightlife of Hollywood. Have dinner at the legendary Musso & Frank Grill and catch a live performance at the Hollywood Bowl if there's a show.
Bedtime
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4.71Santa Monica Pier
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4.71Santa Monica Pier
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4.69Hollywood
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4.69Hollywood
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Iconic Sights of LA and Hollywood
Morning
Start your day with a guided tour of the Hollywood Walk of Fame. Afterward, visit the world-famous Griffith Observatory for panoramic views of the city. Grab a coffee at Go Get Em Tiger in Los Feliz.
Afternoon
Enjoy a leisurely lunch at Sqirl in Silver Lake, known for its delicious seasonal dishes. Take a stroll along Rodeo Drive in Beverly Hills and do some window shopping.
Evening
Dine at the trendy Bavel in the Arts District. End the night with a visit to the historic The Magic Castle for a unique and magical experience.
Bedtime
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4.63Hollywood Walk of Fame
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4.63Hollywood Walk of Fame
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4.71Griffith Observatory
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4.71Griffith Observatory
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Beach Day and Culinary Delights
Morning
Spend the morning relaxing at Venice Beach. Grab a casual brunch at Gjusta, a local favorite for its artisanal bread and pastries.
Afternoon
Explore the colorful streets of Muscle Beach and enjoy the bohemian vibe of Abbot Kinney Boulevard. Have a late lunch at The Tasting Kitchen.
Evening
Indulge in a fine dining experience at Providence, known for its exquisite seafood. After dinner, take a romantic walk along the Santa Monica Pier.
Bedtime
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4.72Venice Beach
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4.72Venice Beach
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Art and Culture in the City of Angels
Morning
Visit the renowned Getty Center and explore its impressive art collection and stunning architecture. Enjoy the panoramic views of the city from the center's garden.
Afternoon
Have a leisurely lunch at the Getty Center Restaurant with a view. Spend the afternoon at the Los Angeles County Museum of Art (LACMA) exploring its diverse exhibits.
Evening
Dine at the iconic The Ivy in West Hollywood, a favorite spot for celebrities. Afterward, experience the vibrant nightlife of the Sunset Strip.
Bedtime
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4.38Los Angeles County Museum of Art
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4.38Los Angeles County Museum of Art
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4.66Sunset Strip
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4.66Sunset Strip
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Outdoor Adventures and Local Eats
Morning
Embark on a hike in Runyon Canyon Park for panoramic views of the city. After your hike, enjoy a hearty brunch at HomeState, known for its Texas-style breakfast tacos.
Afternoon
Explore the trendy shops and cafes on Melrose Avenue. Stop for a coffee at Alfred Coffee and do some shopping.
Evening
Dine at Bavel, a popular restaurant serving modern Middle Eastern cuisine. End the night with a cocktail at the speakeasy The Varnish.
Bedtime
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4.63Runyon Canyon Park
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4.63Runyon Canyon Park
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Surf, Turf, and Hollywood Glamour
Morning
Take a surfing lesson at Santa Monica Beach and experience the laid-back California lifestyle. After your lesson, enjoy a seafood lunch at The Lobster.
Afternoon
Visit the historic TCL Chinese Theatre and take a stroll along the Hollywood Walk of Fame. Have a coffee at the classic Musso & Frank Grill.
Evening
Dine at Republique, a popular French bistro housed in a beautiful historic building. After dinner, catch a show at the Hollywood Bowl.
Bedtime
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4.71Santa Monica Beach
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4.71Santa Monica Beach
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4.61TCL Chinese Theatre
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4.61TCL Chinese Theatre
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City of Stars and Culinary Delights
Morning
Embark on a guided tour of Hollywood and learn about the history of the entertainment industry. Visit the Dolby Theatre, home of the Academy Awards.
Afternoon
Enjoy a leisurely lunch at Griffith Observatory Cafe at the End of the Universe with a view of the iconic Hollywood sign. Explore the exhibits at the El Capitan Theatre.
Evening
Dine at Bavel, a popular restaurant serving modern Middle Eastern cuisine. After dinner, take a romantic walk along the Sunset Strip.
Bedtime
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4.69Hollywood
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4.69Hollywood
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4.50Dolby Theatre
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4.50Dolby Theatre
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Beach Day and Hollywood Magic
Morning
Spend the morning relaxing at Santa Monica Beach. Take a walk along the Santa Monica Pier and enjoy the ocean views. Have a casual brunch at The Misfit Restaurant + Bar.
Afternoon
Visit the iconic Third Street Promenade for some shopping and street performances. Have a coffee at Blue Bottle Coffee and enjoy the lively atmosphere.
Evening
Dine at The Lobster, a historic seafood restaurant with stunning views of the Pacific Ocean. After dinner, take a romantic sunset cruise from Marina del Rey.
Bedtime
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4.71Santa Monica Beach
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4.71Santa Monica Beach
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4.71Santa Monica Pier
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4.71Santa Monica Pier
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Culinary Delights and Hollywood Glamour
Morning
Start your day with a visit to the Los Angeles County Museum of Art (LACMA) and explore its impressive art collection. Have a coffee at Stumptown Coffee Roasters in the museum.
Afternoon
Enjoy a leisurely lunch at The Ivy, a favorite spot for celebrities. Afterward, take a stroll along Rodeo Drive in Beverly Hills and do some window shopping.
Evening
Dine at the iconic Spago in Beverly Hills, known for its innovative cuisine. After dinner, catch a show at the Hollywood Bowl.
Bedtime
Find amazing hotels in Los Angeles.
4.38Los Angeles County Museum of Art
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4.38Los Angeles County Museum of Art
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4.65Rodeo Drive
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4.65Rodeo Drive
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Surf, Turf, and Hollywood Glamour
Morning
Take a surfing lesson at Venice Beach and experience the laid-back California lifestyle. After your lesson, enjoy a seafood lunch at The Albright.
Afternoon
Visit the historic TCL Chinese Theatre and take a stroll along the Hollywood Walk of Fame. Have a coffee at the classic Musso & Frank Grill.
Evening
Dine at Republique, a popular French bistro housed in a beautiful historic building. After dinner, catch a show at the Hollywood Bowl.
Bedtime
Find amazing hotels in Los Angeles.
4.72Venice Beach
Book Now
4.72Venice Beach
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4.61TCL Chinese Theatre
Book Now
4.61TCL Chinese Theatre
Book Now
City of Stars and Culinary Delights
Morning
Embark on a guided tour of Hollywood and learn about the history of the entertainment industry. Visit the Dolby Theatre, home of the Academy Awards.
Afternoon
Enjoy a leisurely lunch at Griffith Observatory Cafe at the End of the Universe with a view of the iconic Hollywood sign. Explore the exhibits at the El Capitan Theatre.
Evening
Dine at Bavel, a popular restaurant serving modern Middle Eastern cuisine. After dinner, take a romantic walk along the Sunset Strip.
Bedtime
Find amazing hotels in Los Angeles.
4.69Hollywood
Book Now
4.69Hollywood
Book Now
4.50Dolby Theatre
Book Now
4.50Dolby Theatre
Book Now
Beach Day and Hollywood Magic
Morning
Spend the morning relaxing at Santa Monica Beach. Take a walk along the Santa Monica Pier and enjoy the ocean views. Have a casual brunch at The Misfit Restaurant + Bar.
Afternoon
Visit the iconic Third Street Promenade for some shopping and street performances. Have a coffee at Blue Bottle Coffee and enjoy the lively atmosphere.
Evening
Dine at The Lobster, a historic seafood restaurant with stunning views of the Pacific Ocean. After dinner, take a romantic sunset cruise from Marina del Rey.
Bedtime
Find amazing hotels in Los Angeles.
4.71Santa Monica Beach
Book Now
4.71Santa Monica Beach
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4.71Santa Monica Pier
Book Now
4.71Santa Monica Pier
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