You might employ numerous methods while organizing a road trip from Chicago to San Diego. Route 66 is significantly more scenic but has many more stop lights and signs. I 70 has a little more to offer than I 80 but is just about as dull—aside from the missile sites—so you can see everything there is after five minutes on I 80. Route 66, also called “The Mother Road,” provides the classic American road trip experience. The famed Route 66 road journey, which runs from Chicago to the Santa Monica Pier and goes through eight nation states and three time zones, is unquestionably one of the most well-known in the world.
You’ll pass by some of the most recognizable roadside sights in the nation along the way, including cheesy Americana, neon signs, and truck stops in remote locations. Chicago to San Diego is a direct drive of 2078 miles (3343 km), which should take one day, and 5 hours to complete in typical traffic. However, you can extend the trip to 7 days to take in the most beautiful sights along the way. On your drive from Chicago to San Diego, use the most picturesque road possible.
Table Of Contents
- 1 Highlights
- 2 Day 1
- 3 Day 2
- 4 Day 3
- 5 Day 4
- 6 South Platte Trail Scenic and Historic Byway to Pawnee Pioneer Trails Scenic & Historic Byway
- 7 Day 5
- 8 Day 6
- 9 Day 7
- Lake Michigan Tour
- Stagecoach Trail
- South Platte Trail Scenic and Historic Byway
- Pawnee Pioneer Trails Scenic & Historic Byway
- Lariat Loop Scenic & Historic Byway
- Mount Evans Scenic Byway
- West Elk Loop
- Colorado National Monument
387 miles — about 7 hours, 59 mins
Chicago to Lake Michigan Tour
Your journey should begin in Chicago and go toward Michigan City. Due to the Lake Michigan trip, Day 1 will be rather long. This drive follows the Lake Michigan shore from New Buffalo to Mackinaw City, Michigan. Chicago, Wisconsin, Indiana, and Quebec, Canada are all accessible via this drive. You can enjoy this drive in sections as a beautiful day trip or the entire way as a multi-day excursion. There are many things to do and see along this fantastic drive. Discover hundreds of miles of shoreline and beaches, a unique dune system, lighthouses, a bevy of state parks, charming coastal villages, museums, vineyards, farm-to-table fare, and numerous options to work out before kicking back with some classic rest. Stop in Suttons Bay after this extended trip.
436 miles — about 7 hours, 59 mins
Lake Michigan Tour to Stagecoach Trail
From the Lake Michigan tour, move to the Stagecoach Trail, the Stagecoach Trail, which was first built in the middle of the 1830s to connect Galena to Chicago, now runs from Galena to Lena. The two-lane road’s gentle curves, mountainous terrain, and lovely, ancient towns make it a favorite among motorcycle riders today. It also runs through a picturesque dairy region. The trip takes about 2.5 hours one way from Chicago and only a few short miles from Dubuque, making it a simple day trip or weekend escape. Ride aboard a model Concord Stagecoach hauled by Belgian draft horses to relive the stagecoach era at the Stagecoach Trails Livery. Reaching Appleton, you can put an end to your day two journey.
467 miles — about 7 hours, 59 mins
Stagecoach Trail to South Platte Trail Scenic and Historic Byway
Head toward South Platte Trail Scenic and Historic Byway as you complete the Stagecoach Trail Drive. This beautiful byway is followed by Country Road 27.8, US Highways 138 and 385, and Colorado Highway 28. This 19-mile loop from Julesburg to Ovid and back along the South Platte River close to the Nebraska border. Trading parties, prospectors looking for gold, and fur trappers moving west in search of riches all frequented this ancient path. Discover a memorial honoring the Pony Express Trail along with local knowledge, petrol, RV parking, and a picnic spot. Stop at 11 pull outs along the journey with interpretative markers outlining the region’s history. Stop in Casey, Iowa, and take a break from the trip. The giant rocking chair in the world is one of the charming tiny town’s many distinctive attractions.
530 miles — about 7 hours, 59 mins
South Platte Trail Scenic and Historic Byway to Pawnee Pioneer Trails Scenic & Historic Byway
The Pawnee Pioneer Trails Magnificent & Historic Byway is another scenic drive you shouldn’t miss on Day 4 of your long journey. This byway is particular because Colorado is known for its 14-ers, which include 54 mountains at least 14,000 feet tall. Discover one of the United States’ remaining short-grass grasslands, a stunningly unusual scene. The enormous open spaces initially appear lonely, yet they teem with animals like coyotes, mule deer, prairie dogs, and raptors. Numerous textures originate from more than 400 plant species, including cottonwood trees, prickly pear cactus, soaptree yuccas, and wildflowers. With a long history, this area was habitant to American Indians before being settled by homesteaders, ranchers, and frontiersmen who later faced difficulties from the elements, the Dust Bowl, and isolation. Drive the beautiful byway for a while, then stop in Sterling before continuing your journey the next day.
405 miles — about 7 hours, 59 mins
Pawnee Pioneer Trails Scenic & Historic Byway to Lariat Loop Scenic & Historic Byway
You can get to Lariat Loop Scenic & Historic Byway by traveling along US Highways 40 and 6, Colorado Highways 470, 6, and 74, and Interstate 70. From Golden, at the foot of the Rockies, the Lariat Loop Scenic and Historic Byway go through the hospitable historic communities of Evergreen and Morrison. Enjoy stunning mountain vistas, lots of outdoor activity activities, and leisure time. Denver’s downtown is only 20 minutes away, making this 40-mile trip the ideal day vacation or weekend break. Learn about Golden, a city that combines history and modernity and offers a variety of dining options, art galleries, specialty shops, and hotel alternatives. A few golden attractions are listed below: The Colorado Railroad Museum will appeal to fans of trains and history. There are more than 100 narrow, regular gauge, steam, and diesel trains. It is open all year.
Lariat Loop Scenic & Historic Byway to Mount Evans Scenic Byway
Navigate to the Mount Evans Scenic Byway. This drive is for you if you enjoy curvy, cliff-hugging roads with breathtaking vistas of mountains, alpine meadows, lakes, mountain goats, and bighorn sheep. In just 27 miles, the highest paved road in North America rises more than 7,000 feet, and every curve reveals breathtaking panoramas. Additionally, there is no more straightforward technique to climb a 14er. This excellent day excursion takes less than an hour from Denver. Starting at Idaho Springs, the drive goes to Mount Evans.
Note The stretch of CO-5 from Echo Lake to Mount Evans is usually open from Memorial Day to Labor Day. It is closed throughout the winter, and visits the Heritage Visitor Center and Museum in Idaho Springs for local knowledge and enlightening displays on the area’s rich history of gold mining, pioneer life, and Native American artifacts. Stop at Eagle, Colorado, after around 8 hours of driving through some of the most beautiful scenery.
413 miles — about 7 hours, 59 mins
Mount Evans Scenic Byway to West Elk Loop
Start day six by traveling in the direction of West Elk Loop. This remote region of western Colorado holds the promise of pristine mountain majesty. The Elk Mountains are fifty-two peaks over 13,000 feet and five over 14,000 feet. Enjoy various exhilarating outdoor sports, or relax while taking in the magnificent scenery. Take your time and spend some time in the picturesque towns along the journey. There is so much to do, like visiting hot springs and wineries.
West Elk Loop to Colorado National Monument
The distance to Colorado National Monument is only a few miles. The Uncompahgre Plateau’s northernmost point is where the Colorado National Monument is situated. Over the past 2 billion years, the Plateau, located more than 2,000 feet above the Colorado River, rose once, entirely eroded, and then rose once more. The Sandstone Plateau extends from this location to Telluride. You enter the breathtaking Colorado National Monument through its East Entrance once you’ve reached Monument Road. The semi-desert landscape along Rim Rock Drive is peppered with juniper and pinyon pine trees, mule deer, gray fox, and Hopi chipmunks.
227 miles — about 3 hours, 52 mins
Colorado National Monument to San Diego, CA
And to conclude, from the monument, head towards San Diego. To get to San Diego, take Rim Rock Drive. And while you’re in town, don’t forget to check out the Torrey Pines State Natural Reserve, which offers six hiking trails ranging from accessible, family-friendly routes to more challenging ones. Here, you can enjoy wind-sculpted sandstone formations and breathtaking vistas of the Pacific Ocean. If you’re up for it, you should trek to Stonewall Peak at Cuyamaca Rancho State Park. You will get a 360-degree panorama of Lake Cuyamaca and the surrounding landscape after you reach the summit.