
Andreas Aydt // Canva
1 / 51. Chicago to Santa Monica
Imagine starting your journey by sinking your teeth into a slice of mouth-watering deep-dish pizza and hitting the road to explore the many fascinating roadside diners that dot the route to Santa Monica!
This epic 2,500-mile adventure is a throwback to old-school romance. There are plenty of surprises and hidden gems waiting to be discovered along the way. From historic landmarks to quirky attractions, this 40-hour drive promises to be an unforgettable experience that will leave you breathless and craving for more!
Any road trip adventure from Chicago to Santa Monica is sure to be fun. Especially since you'll be driving along the iconic Route 66. However, it's extra special for a couple to take on as the "Mother Road" provides unforgettable memories at places like the Art Institute of Chicago, the Blue Dome Entertainment District, the Cadillac Ranch, the Petrified Forest National Park, and the Santa Monica Pier.
Parking in Chicago is difficult but not impossible, but to be on the safe side, make sure to have a spot booked in advance before you head out!












