15 Days Route 66 Road Trip from Chicago to Santa Monica Itinerary

Enjoy a leisurely breakfast at Cafe Ba-Ba-Reeba before exploring the Art Institute of Chicago with a guided tour Chicago Art Institute of Chicago Guided Tour to admire its renowned collection.

For lunch, head to Gino's East for a taste of Chicago-style pizza. Continue your cultural journey with a visit to the Chicago Loop Chicago Loop and the Chicago Board of Trade Building Chicago Board of Trade Building for architectural marvels.

Dine at the elegant The Signature Room at the 95th with stunning views of the city skyline. Wrap up your day with a relaxing Chicago River Cruise Chicago Architecture River Cruise Skip-the-Ticket Line.

Start your day with a hearty breakfast at Longman & Eagle. Embark on a thrilling adventure with a Chicago Craft Brewery Tour by Barrel Bus Chicago Craft Brewery Tour by Barrel Bus to taste local brews.

For lunch, try the unique dishes at Kuma's Corner. Explore the city's neighborhoods with a Chicago Lakefront Neighborhoods Bike Tour Chicago Lakefront Neighborhoods Bike Tour for a different perspective.

Dine at the innovative Avec for a memorable culinary experience. End your day with a visit to the United Center United Center for sports excitement.

Enjoy a delightful breakfast at Cafe Marie-Jeanne. Dive into the culinary scene of Chicago with a Secret Food Tour Chicago Secret Food Tour to taste local specialties.

For lunch, savor the flavors at Frontera Grill. Discover the city's history with a Chicago History Museum Admission Chicago History Museum Admission Ticket for an enriching experience.

Indulge in a gourmet dinner at Monteverde to satisfy your taste buds. Conclude your day with a visit to the iconic Marina City Marina City.

Start your day with a cozy breakfast at Fat Rice. Relax and unwind with a Chicago Riverboat Tour Chicago River 1.5-Hour Guided Architecture Riverboat Tour to enjoy the city's skyline.

For lunch, try the delicious dishes at Crisp. Explore the city's hidden gems with a Secret Interiors Architecture Walking Tour Chicago Secret Interiors Architecture Walking Tour for architectural wonders.

Enjoy a leisurely dinner at Parachute and experience the city's culinary creativity. End your day with a visit to the iconic Chicago River Chicago River 1.5-Hour Guided Architecture Cruise.

Savor a delicious breakfast at Cellar Door Provisions. Explore the city's vibrant neighborhoods with a Chicago Ultimate City Attractions Bike Tour Chicago Ultimate City Attractions Bike Tour for a fun morning.

For lunch, enjoy the flavors at The Bristol. Visit the iconic Willis Tower Willis Tower for panoramic views of the city in the afternoon.

Conclude your Chicago journey with a farewell dinner at Giant and reminisce about your adventures. End your day with a visit to the iconic Navy Pier Navy Pier for a relaxing evening.

Travel from Chicago to Santa Monica with a private transfer.

Arrive in Santa Monica and enjoy a relaxing afternoon at Santa Monica Beach and Pier Santa Monica Beach and Pier.

Dine at The Lobster and savor fresh seafood while enjoying the ocean views. Relax at The Bungalow Santa Monica The Bungalow Santa Monica for drinks and a laid-back atmosphere.