Embark on a 17-day journey that seamlessly blends the urban allure of Chicago with the laid-back vibes of Santa Monica. Chicago, known for its stunning architecture and rich history, offers a plethora of cultural experiences. Meanwhile, Santa Monica provides a serene escape with its iconic pier and beautiful beaches. This itinerary is crafted to balance relaxation with exploration, ensuring you experience the best of both worlds.

Chicago, the Windy City, is a hub of architectural marvels and cultural landmarks. From the towering skyscrapers to the vibrant arts scene, there's something for everyone. Santa Monica, on the other hand, is a coastal paradise with a relaxed atmosphere, perfect for unwinding. Its proximity to Los Angeles also makes it an ideal base for exploring Southern California's attractions.

With a budget-conscious approach, this itinerary ensures you enjoy the highlights of each destination without breaking the bank. From sightseeing tours to local dining experiences, every detail is designed to provide a memorable and relaxing vacation.

Chicago

Days 1-8: Exploring the Windy City

Begin your adventure in Chicago, a city renowned for its architectural beauty and vibrant culture. Start with a Chicago River 90-Minute Architecture Tour to marvel at the city's iconic skyline.

For accommodations, consider staying at The Peninsula Chicago for a luxurious experience, or opt for the Freehand Chicago for a more budget-friendly option.

Don't miss the Skydeck Chicago for breathtaking views from the 103rd floor of Willis Tower.

For a taste of local cuisine, head to Lou Malnati's Pizzeria for deep-dish pizza or try the famous Chicago-style hot dogs at Portillo's. For breakfast, visit Wildberry Pancakes and Cafe for a hearty start to your day.

Explore the city's museums, such as the Art Institute of Chicago and the Field Museum. The Field Museum offers a fascinating glimpse into natural history.

For a relaxing evening, consider a Lake Michigan Sunset Cruise to enjoy the city skyline as the sun sets.

Santa Monica

Days 9-17: Coastal Relaxation and Exploration

Fly from Chicago to Los Angeles using Trip.com for convenient flight options. Upon arrival, head to Santa Monica, where the beach awaits.

Stay at the Shore Hotel for ocean views or the Ocean View Hotel for a more budget-friendly stay.

Start your Santa Monica experience with a Perfect 5 ½ Hour LA & Hollywood Tour to see the highlights of Los Angeles, including Hollywood and Beverly Hills.

For a unique experience, join a Luxury Shared E-Boat Cruise with wine and charcuterie, perfect for a relaxing afternoon.

Indulge in local flavors at The Misfit Restaurant + Bar, known for its farm-to-table dishes, or enjoy seafood at Blue Plate Oysterette. For breakfast, try Huckleberry Bakery & Café for freshly baked pastries.

Spend your days exploring the Santa Monica Pier, relaxing on the beach, or taking a bike ride along the scenic coastal path. Capture stunning photos of the Pacific Ocean and the vibrant street art around Venice Beach.

As your journey concludes, reflect on the diverse experiences from the architectural wonders of Chicago to the serene beaches of Santa Monica. This itinerary offers a perfect blend of culture, relaxation, and adventure, leaving you with unforgettable memories.