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The Ultimate Route 66 Cross-Country Odyssey

Embark on the definitive American road trip from Chicago to the Pacific. This 14-day journey follows the 'Mother Road' at a relaxed pace, ensuring ample time for quirky roadside attractions, neon-lit diners, and historic museums. You will traverse eight states, shifting from the Midwestern prairies to the high deserts of New Mexico and Arizona, finally reaching the iconic Santa Monica Pier for a classic California su

14days
42stops
2637km

The route

Tap a day or a town

You sleep in Chicago · Springfield · St. Louis · Lebanon · Catoosa · Clinton · Amarillo · Santa Fe · Albuquerque · Holbrook · Flagstaff · Oatman · San Bernardino — start in Chicago, end in Santa Monica.

DAY01

Route 66 Begin Sign → Millennium Park

8.6 km · 21m driving · Overnight in Millennium Park
  1. 09:00
    ⭐ Route 66 Begin Sign· start
  2. 5.4 km · 12m
  3. 12:00
    Lou Mitchell's
  4. 3.2 km · 9m
  5. 15:00
    Millennium Park· overnight
DAY02

Gemini Giant → Cozy Dog Drive In

167 km · 1h 49m driving · Overnight in Cozy Dog Drive In
  1. 09:00
    Gemini Giant· start
  2. 97 km · 1h 5m
  3. 12:00
    ⭐ Pontiac Route 66 Museum
  4. 70 km · 44m
  5. 15:00
    Cozy Dog Drive In· overnight
DAY03

Old Chain of Rocks Bridge → Ted Drewes Frozen Custard

186 km · 1h 45m driving · Overnight in Ted Drewes Frozen Custard
  1. 09:00
    ⭐ Old Chain of Rocks Bridge· start
  2. 148 km · 1h 22m
  3. 12:00
    Gateway Arch
  4. 38 km · 23m
  5. 15:00
    Ted Drewes Frozen Custard· overnight
DAY04

Meramec Caverns → Munger Moss Motel

221 km · 2h 16m driving · Overnight in Munger Moss Motel
  1. 09:00
    ⭐ Meramec Caverns· start
  2. 104 km · 1h 6m
  3. 12:00
    Devil's Elbow Bridge
  4. 117 km · 1h 10m
  5. 15:00
    Munger Moss Motel· overnight
DAY05

Cars on the Route → Blue Whale of Catoosa

229 km · 2h 12m driving · Overnight in Blue Whale of Catoosa
  1. 09:00
    ⭐ Cars on the Route· start
  2. 219 km · 2h 3m
  3. 12:00
    Rainbow Bridge
  4. 10 km · 9m
  5. 15:00
    Blue Whale of Catoosa· overnight
DAY06

Buck Atom's Cosmic Curios → Oklahoma Route 66 Museum

170 km · 1h 44m driving · Overnight in Oklahoma Route 66 Museum
  1. 09:00
    Buck Atom's Cosmic Curios· start
  2. 26 km · 20m
  3. 12:00
    ⭐ Pops 66 Soda Ranch
  4. 145 km · 1h 24m
  5. 15:00
    Oklahoma Route 66 Museum· overnight
DAY07

Tower Station and U-Drop Inn → Cadillac Ranch

270 km · 2h 30m driving · Overnight in Cadillac Ranch
  1. 09:00
    ⭐ Tower Station and U-Drop Inn· start
  2. 129 km · 1h 12m
  3. 12:00
    The Big Texan Steak Ranch
  4. 142 km · 1h 18m
  5. 15:00
    Cadillac Ranch· overnight
DAY08

Midpoint Café → Santa Fe

164 km · 1h 32m driving · Overnight in Santa Fe Plaza
  1. 09:00
    Midpoint Café· start
  2. 64 km · 36m
  3. 12:00
    ⭐ Blue Swallow Motel
  4. 100 km · 56m
  5. 15:00
    Santa Fe Plaza· overnight
DAY09

Loretto Chapel → 66 Diner

104 km · 1h 3m driving · Overnight in 66 Diner
  1. 09:00
    Loretto Chapel· start
  2. 0.4 km · 2m
  3. 12:00
    ⭐ Old Town Albuquerque
  4. 104 km · 1h 1m
  5. 15:00
    66 Diner· overnight
DAY10

El Rancho Hotel → Wigwam Motel

338 km · 3h 5m driving · Overnight in Wigwam Motel
  1. 09:00
    El Rancho Hotel· start
  2. 223 km · 2h 1m
  3. 12:00
    ⭐ Petrified Forest National Park
  4. 115 km · 1h 4m
  5. 15:00
    Wigwam Motel· overnight
DAY11

Standin' on the Corner Park → Lowell Observatory

93 km · 1h 2m driving · Overnight in Lowell Observatory
  1. 09:00
    ⭐ Standin' on the Corner Park· start
  2. 52 km · 33m
  3. 12:00
    Meteor Crater Natural Landmark
  4. 42 km · 29m
  5. 15:00
    Lowell Observatory· overnight
DAY12

Delgadillo's Snow Cap → Oatman

219 km · 2h 9m driving · Overnight in Oatman Ghost Town
  1. 09:00
    Delgadillo's Snow Cap· start
  2. 123 km · 1h 13m
  3. 12:00
    ⭐ Hackberry General Store
  4. 97 km · 56m
  5. 15:00
    Oatman Ghost Town· overnight
DAY13

Roy's Motel & Café → Wigwam Motel No. 7

334 km · 3h 39m driving · Overnight in Wigwam Motel No. 7
  1. 09:00
    ⭐ Roy's Motel & Café· start
  2. 166 km · 1h 52m
  3. 12:00
    Elmer's Bottle Tree Ranch
  4. 168 km · 1h 47m
  5. 15:00
    Wigwam Motel No. 7· overnight
DAY14

The Original McDonald's Museum → 66 End of the Trail Sign

133 km · 1h 33m driving
  1. 09:00
    The Original McDonald's Museum· start
  2. 7.1 km · 12m
  3. 12:00
    ⭐ Santa Monica Pier
  4. 126 km · 1h 21m
  5. 15:00
    66 End of the Trail Sign
Booking timeline
Book these before you go
  1. Stay in Springfield & St. Louis · 2
  2. Stay in Santa Fe & Albuquerque · 2
  3. Stay in Williams or Flagstaff · 2
Heads Up
  • Book historic motels like the Blue Swallow or Wigwam Villages at least 6-9 months in advance.
  • Many classic diners close early; plan your lunch and dinner stops before 7:00 PM in rural areas.
  • Expect significant temperature swings between the Chicago lakefront and the Mojave Desert.
  • Keep a physical Route 66 map handy as GPS often defaults to faster interstate bypasses.