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Route 66: The Mother Road Part 1
This is the start of the ultimate American pilgrimage. Since you've got 14 days, we're going to take this at a classic pace—no rushing the neon signs or the quirky roadside diners. We're kicking off in the Windy City and making our way through the heart of the Midwest.
5days
22stops
DAY01
Chicago → Navy Pier
Overnight in Navy Pier
- 09:00Chicago O'Hare International Airport· start
- 11:00Route 66 Begin Sign
- 13:00Lou Mitchell's
- 15:30Willis Tower
- 18:00Navy Pier· overnight
DAY02
Depart Chicago → Illinois State Capitol
Overnight in Illinois State Capitol
- 09:00Depart Chicago· start
- 10:30Gemini Giant
- 12:30Pontiac
- 15:00Cozy Dog Drive In
- 17:00Illinois State Capitol· overnight
DAY03
Henry's Rabbit Ranch → Ted Drewes Frozen Custard
Overnight in Ted Drewes Frozen Custard
- 09:00Henry's Rabbit Ranch· start
- 11:30Old Chain of Rocks Bridge
- 14:00Gateway Arch
- 16:30Ted Drewes Frozen Custard· overnight
DAY04
Meramec Caverns → Gary's Gay Parita
Overnight in Gary's Gay Parita
- 09:00Meramec Caverns· start
- 12:30Cuba, Missouri
- 15:00Munger Moss Motel
- 17:30Gary's Gay Parita· overnight
DAY05
Cars on the Route → Buck Atom's Cosmic Curios
- 09:00Cars on the Route· start
- 11:30Rainbow Bridge
- 14:00Blue Whale of Catoosa
- 17:00Buck Atom's Cosmic Curios
Heads Up
- Keep an eye out for the "Historic Route 66" brown signs; the road often runs parallel to I-55 and I-44, but the old alignments are where the magic is.