The Mother Road: Chicago to Santa Monica
A nostalgic 14-day journey across eight states following the historic Route 66. Experience the neon signs, vintage diners, and quirky roadside Americana that define the spirit of the open road from the Great Lakes to the Pacific.
- Route 66 Begin Sign
- Pontiac Route 66 Museum
- Meramec Caverns
- Blue Whale of Catoosa
- Pops 66 Soda Ranch
- Oklahoma Route 66 Museum
- Cadillac Ranch
- Santa Fe Plaza
Chicago Beginnings and Neon Lights
Route 66 Begin Sign
Route 66 Begin Sign, Chicago, Illinois, US
Lou Mitchell's
Lou Mitchell's, Chicago, Illinois, US
Gemini Giant
Gemini Giant, Wilmington, Illinois, US
Illinois Prairies and Lincoln Heritage
Pontiac Route 66 Museum
Pontiac Route 66 Museum, Pontiac, Illinois, US
Cozy Dog Drive In
Cozy Dog Drive In, Springfield, Illinois, US
Old Chain of Rocks Bridge
Old Chain of Rocks Bridge, St. Louis, Missouri, US
Missouri Ozarks and Cavern Tours
Gateway Arch
Gateway Arch, St. Louis, Missouri, US
Meramec Caverns
Meramec Caverns, Stanton, Missouri, US
Cuba Wagon Wheel Motel
Cuba Wagon Wheel Motel, Cuba, Missouri, US
Kansas Corner and Oklahoma Hills
Cars on the Route
Cars on the Route, Galena, Kansas, US
Blue Whale of Catoosa
Blue Whale of Catoosa, Catoosa, Oklahoma, US
Tulsa Arts District
Tulsa Arts District, Tulsa, Oklahoma, US
Oklahoma City and Neon Dreams
Rock Cafe
Rock Cafe, Stroud, Oklahoma, US
Pops 66 Soda Ranch
Pops 66 Soda Ranch, Arcadia, Oklahoma, US
Oklahoma City National Memorial
Oklahoma City National Memorial, Oklahoma City, Oklahoma, US
Western Oklahoma and Texas Panhandle
Lucille's Service Station
Lucille's Service Station, Hydro, Oklahoma, US
Oklahoma Route 66 Museum
Oklahoma Route 66 Museum, Clinton, Oklahoma, US
U-Drop Inn
U-Drop Inn, Shamrock, Texas, US
Cadillacs and the Midpoint Cafe
Cadillac Ranch
Cadillac Ranch, Amarillo, Texas, US
Midpoint Cafe
Midpoint Cafe, Adrian, Texas, US
Tucumcari Blue Swallow Motel
Tucumcari Blue Swallow Motel, Tucumcari, New Mexico, US
High Desert and Santa Fe Detour
Santa Fe Plaza
Santa Fe Plaza, Santa Fe, New Mexico, US
Canyon Road
Canyon Road, Santa Fe, New Mexico, US
Old Town Albuquerque
Old Town Albuquerque, Albuquerque, New Mexico, US
Red Rocks and Painted Deserts
El Rancho Hotel
El Rancho Hotel, Gallup, New Mexico, US
Petrified Forest National Park
Petrified Forest National Park, Holbrook, Arizona, US
Wigwam Motel
Wigwam Motel, Holbrook, Arizona, US
Standing on the Corner in Winslow
Standin' on the Corner Park
Standin' on the Corner Park, Winslow, Arizona, US
Meteor Crater
Meteor Crater, Winslow, Arizona, US
Flagstaff Visitor Center
Flagstaff Visitor Center, Flagstaff, Arizona, US
Grand Canyon and Seligman Kitsch
Grand Canyon Mather Point
Grand Canyon Mather Point, Grand Canyon Village, Arizona, US
Delgadillo's Snow Cap
Delgadillo's Snow Cap, Seligman, Arizona, US
Kingman Powerhouse Museum
Kingman Powerhouse Museum, Kingman, Arizona, US
Oatman Burros and Mojave Sands
Oatman Ghost Town
Oatman Ghost Town, Oatman, Arizona, US
Roy's Motel & Cafe
Roy's Motel & Cafe, Amboy, California, US
Barstow Station
Barstow Station, Barstow, California, US
Bottle Trees and San Bernardino
Elmer's Bottle Tree Ranch
Elmer's Bottle Tree Ranch, Oro Grande, California, US
Original McDonald's Museum
Original McDonald's Museum, San Bernardino, California, US
Wigwam Motel No. 7
Wigwam Motel No. 7, San Bernardino, California, US
The Final Stretch to the Pacific
Fair Oaks Pharmacy
Fair Oaks Pharmacy, South Pasadena, California, US
Santa Monica Pier
Santa Monica Pier, Santa Monica, California, US
End of the Trail Sign
End of the Trail Sign, Santa Monica, California, US
- Many original Route 66 segments are now frontage roads or bypassed by I-40; look for 'Historic Route 66' brown signs.
- Book iconic motels like the Blue Swallow or Wigwam Village at least 6-9 months in advance for 2026.
- The stretch through the Mojave Desert (Day 12) is extremely hot; ensure your vehicle's cooling system is serviced and carry extra water.
- Some roadside attractions have seasonal hours; verify opening times for smaller museums in Illinois and Oklahoma.
- Day 4: 5h 1m driving — plan rest stops