5-Day Chicago to California Road Trip Itinerary

Begin your day with a visit to the Skydeck Chicago at Willis Tower (Sears Tower). Take in breathtaking views from one of the tallest buildings in the Western Hemisphere.

Explore more architectural wonders by visiting Marina City and taking a walk along the scenic Chicago Riverwalk. Stop for lunch at one of the many cafes along the riverwalk.

Dine at RPM Italian , known for its modern Italian cuisine. End your evening with a visit to The Magnificent Mile, where you can shop or simply enjoy the vibrant atmosphere.

Start your morning with a trip to Field Museum, home to extensive exhibits on natural history. Don't miss Sue, the largest and most complete T. rex ever discovered.

After exploring the museum, head over to Shedd Aquarium for an underwater adventure. Enjoy lunch at one of their on-site cafes while taking in views of Lake Michigan.

For dinner, make reservations at one of Chicago's renowned restaurants (suggestion: local favorite). Afterward, enjoy an evening stroll through Grant Park, often referred to as "Chicago's front yard."

Spend your morning exploring Navy Pier, which offers attractions like rides, shops, and beautiful lakefront views. Grab coffee or breakfast from one of its many eateries.

Visit the historic Wrigley Field for a tour if available or simply admire it from outside. Have lunch nearby before heading out on your road trip towards California.

As you begin your journey towards California in the evening, consider stopping by small towns along your route for dinner and rest.

Start your day with a visit to the iconic Golden Gate Bridge. Walk or bike across the bridge to take in the stunning views of San Francisco Bay and the city skyline. Afterward, enjoy a leisurely breakfast at a nearby café.

Head to Fisherman's Wharf for lunch and explore its many attractions, including Pier 39, where you can see sea lions basking in the sun. Don't miss out on trying some fresh seafood at one of the local eateries.

Conclude your day with a visit to Alcatraz Island. Take an evening tour of the infamous former prison and learn about its history. After returning to the city, enjoy dinner at one of San Francisco's renowned restaurants.