New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.
Iconic Route 66 Road Trip from Chicago to Los Angeles Itinerary
Last updated: 2024 Jun 14Starting the Legendary Route 66 Journey
Morning
Begin your iconic Route 66 road trip at the historic Palmer House Hilton, where you can immerse yourself in the elegance of the hotel before hitting the road. Enjoy a classic Chicago breakfast at Lou Mitchell's, a favorite stop for Route 66 travelers.
Afternoon
Explore the starting point of Route 66 at Grant Park, home to the famous Route 66 Begin sign. Afterward, have a leisurely lunch at The Berghoff, a German restaurant with a long history along the route.
Evening
In the evening, take a stroll down the vibrant Chicago Riverwalk and enjoy dinner at The Signature Room at the 95th, where you can savor a meal with a view of the city skyline.
Bedtime
Find amazing hotels in Chicago, Illinois.
Popular
Palmer House Hilton
click to access prices
Popular
Grant Park
click to access prices
Popular
Chicago Riverwalk
click to access prices
Immersing in Chicago's Culture and Cuisine
Morning
Start your day with a visit to the iconic Art Institute of Chicago. After exploring the art collections, have a delightful brunch at The Purple Pig, known for its Mediterranean-inspired dishes.
Afternoon
Spend the afternoon at the Willis Tower Skydeck and The Ledge, where you can enjoy panoramic views of the city. For lunch, head to Giordano's for a taste of Chicago's famous deep-dish pizza.
Evening
In the evening, experience the city's vibrant food scene with a dinner at Girl & the Goat, a renowned restaurant offering a creative menu. Afterward, take a leisurely walk along The Magnificent Mile.
Bedtime
Find amazing hotels in Chicago, Illinois.
Popular
Art Institute of Chicago
click to access prices
Popular
Chicago Willis Tower Skydeck and The Ledge Ticket
click to access prices
Popular
The Magnificent Mile
click to access prices
Exploring Chicago's Architectural Marvels
Morning
Embark on the Chicago Architecture Center Cruise on Chicago's First Lady to learn about the city's iconic buildings. Enjoy a light breakfast at Xoco, known for its Mexican cuisine.
Afternoon
After the cruise, visit the Museum of Science and Industry to delve into the world of science and innovation. For lunch, try the famous Chicago hot dogs at Portillo's Hot Dogs.
Evening
End the day with a sunset cocktail on the Chicago River Guided Sunset Cocktail & Architecture Tour. For dinner, savor the flavors of Italy at Eataly Chicago.
Bedtime
Find amazing hotels in Chicago, Illinois.
Popular
Chicago Architecture Center Cruise on Chicago's First Lady
click to access prices
Popular
Museum of Science and Industry
click to access prices
Popular
Chicago River Guided Sunset Cocktail & Architecture Tour
click to access prices
Discovering the Capital of Illinois
Morning
Depart from Chicago and head to Springfield, the capital of Illinois. Visit the Abraham Lincoln Presidential Library and Museum to learn about the life of the 16th President of the United States. Enjoy a hearty breakfast at D'Arcy's Pint.
Afternoon
Explore the Illinois State Capitol and take a guided tour of the historic building. For lunch, try the local favorite, the Horseshoe sandwich, at D'Arcy's Pint.
Evening
In the evening, take a leisurely walk around the Lincoln Home National Historic Site and enjoy a relaxed dinner at Maldaner's Restaurant.
Bedtime
Find amazing hotels in Springfield, Illinois.
Popular
South Beach
click to access prices
Gateway to the West
Morning
Continue your journey to St. Louis, Missouri, known for the iconic Gateway Arch. Visit the Gateway Arch National Park and take a tram ride to the top for stunning views of the city. Enjoy a classic St. Louis breakfast at Rooster.
Afternoon
Explore the City Museum, a unique attraction that offers a blend of playground, funhouse, and architectural marvel. For lunch, try the local favorite, toasted ravioli, at Charlie Gitto's on the Hill.
Evening
Conclude your day with a dinner cruise on the Mississippi River aboard the Gateway Arch Riverboats. Savor a delicious meal while taking in the views of the city.
Bedtime
Find amazing hotels in St. Louis, Missouri.
Popular
From Interlaken Local Canyoning Trip
click to access prices
Popular
Museum of Science Boston
click to access prices
Adjacent Cities
Find the right stay during your trip.