Route 66 centennial celebrated with new sign at Navy Pier
Mar 25, 2026
U.S. Route 66 is a cultural landmark that holds the rich history of America’s automotive and commercial boom, and the memories of countless family roadtrips. The storied highway, which spans 2,400 miles between Chicago to California, is celebrating its centennial this year. Chicago honored the lan
dmark Wednesday by unveiling a new sign at Navy Pier outside of Harry Caray’s Tavern.Vintage cars surrounded the sign as city leaders and preservationists gathered to mark the milestone.One of the speakers, Bill Thomas, said he was 8-years-old during his first trip on Route 66 to Disneyland. He recalled the grueling temperatures and "adventure" of it all. That's something he appreciates now as commissioner of the U.S. Route 66 Centennial Commission.“We drove through the desert and it was 100 degrees," said Thomas, 71. "This is part of the experience."
An impersonator of President Abraham Lincoln salutes during the National Anthem to kick off a news conference Wednesday to recognize Navy Pier as the starting point of Route 66 near Harry Caray’s restaurant.
|
Ashlee Rezin/Sun-Times
1 of 17
Attendees look at alpaca before the start of a news conference Wednesday to recognize Navy Pier as the starting point of Route 66 near Harry Caray’s restaurant.
|
Ashlee Rezin/Sun-Times
2 of 17
The Plain White T’s perform Wednesday before the start of a news conference to recognize Navy Pier as the starting point of Route 66 near Harry Caray’s restaurant. This year is the 100th anniversary of Route 66, which Caray traveled to announce his first game in 1945.
|
Ashlee Rezin/Sun-Times
3 of 17
Supporters watch as a sign is unveiled Wednesday during a news conference to recognize Navy Pier as the starting point of Route 66 near Harry Caray’s restaurant. This year is the 100th anniversary of Route 66, which Caray traveled to announce his first game in 1945.
|
Ashlee Rezin/Sun-Times
4 of 17
A sign is unveiled Wednesday during a news conference to recognize Navy Pier as the starting point of Route 66 near Harry Caray’s restaurant.
|
Ashlee Rezin/Sun-Times
5 of 17
Supporters celebrate as a sign is unveiled Wednesday during a news conference to recognize Navy Pier as the starting point of Route 66 near Harry Caray’s restaurant. This year is the 100th anniversary of Route 66, which Caray traveled to announce his first game in 1945.
|
Ashlee Rezin/Sun-Times
6 of 17
An impersonator of President Abraham Lincoln greets attendees Wednesday for a news conference to recognize Navy Pier as the starting point of Route 66 near Harry Caray’s restaurant.
|
Ashlee Rezin/Sun-Times
7 of 17
Former Chicago Cub Ryan Dempster speaks Wednesday during a news conference to recognize Navy Pier as the starting point of Route 66 near Harry Caray’s restaurant.
|
Ashlee Rezin/Sun-Times
8 of 17
Wayne Messmer sings the National Anthem during a news conference Wednesday to recognize Navy Pier as the starting point of Route 66 near Harry Caray’s restaurant.
|
Ashlee Rezin/Sun-Times
9 of 17
Mayor Brandon Johnson speaks Wednesday during a news conference to recognize Navy Pier as the starting point of Route 66 near Harry Caray’s restaurant.
|
Ashlee Rezin/Sun-Times
10 of 17
Marilynn Gardner, CEO of Navy Pier Inc., speaks Wednesday during a news conference to recognize Navy Pier as the starting point of Route 66 near Harry Caray’s restaurant. This year is the 100th anniversary of Route 66, which Caray traveled to announce his first game in 1945.
|
Ashlee Rezin/Sun-Times
11 of 17
Former Gov. Pat Quinn speaks Wednesday during a news conference to recognize Navy Pier as the starting point of Route 66 near Harry Caray’s restaurant.
|
Ashlee Rezin/Sun-Times
12 of 17
Barbara Hopkins attends a news conference Wednesday to recognize Navy Pier as the starting point of Route 66 near Harry Caray’s restaurant.
|
Ashlee Rezin/Sun-Times
13 of 17
Catie Sheehan, of the Illinois Office of Tourism, speaks Wednesday during a news conference to recognize Navy Pier as the starting point of Route 66 near Harry Caray’s restaurant. This year is the 100th anniversary of Route 66, which Caray traveled to announce his first game in 1945.
|
Ashlee Rezin/Sun-Times
14 of 17
Mayor Brandon Johnson speaks Wednesday during a news conference to recognize Navy Pier as the starting point of Route 66 near Harry Caray’s restaurant.
|
Ashlee Rezin/Sun-Times
15 of 17
Bill Thomas, of the Illinois’ Route 66 Centennial Celebration Commission, speaks Wednesday during a news conference to recognize Navy Pier as the starting point of Route 66 near Harry Caray’s restaurant. This year is the 100th anniversary of Route 66, which Caray traveled to announce his first game in 1945.
|
Ashlee Rezin/Sun-Times
16 of 17
Grant DePorter, CEO of Harry Caray’s Restaurant Group, speaks Wednesday during a news conference to recognize Navy Pier as the starting point of Route 66 near Harry Caray’s restaurant.
|
Ashlee Rezin/Sun-Times
17 of 17
He said Route 66, commissioned in 1926, gave Americans the opportunity to be free. That meant a better, higher quality of life, he said.The officially recognized start of the iconic highway in Illinois has moved at least twice before. There are multiple signs honoring those locations. One of them stands at Adams Street and Wabash Avenue.The new signage at Navy Pier was chosen by the Route 66 Commission and city of Chicago chose Navy Pier, tying the city even more closely to the highway’s national story.Route 66's path was first laid out by indigenous groups who used animal footprints to guide the road. They created trade routes that directed the path we know today.What was once “America’s Main Street” was decommissioned and removed from the U.S. highway system in 1985. As commercial needs grew, and the nation adopted what’s now the interstate highway system, Route 66 became an open road for motor enthusiasts and tourism.“I have yet to find a demographic group or culture who doesn't have a connection with Route 66,” Thomas said.But not every group could experience Route 66 in the same way.Black travelers had to avoid sundown towns, and leaned on a publication called “The Green Book” to locate lodging, dining and gas stations where they could patronize. Thomas said hardly any of those original structures still exist.During the segregation era, permitted locations for Black travelers were sometimes half a mile off of the road. After severe dust storms, many landmarks along the route were destroyed.Preservationists like Thomas are working to restore the road’s legacy. Along with the route’s tourist attractions, cultural staples like the famous song “Route 66” by Bobby Troup and the Disney Pixar movie Cars keep the story of Route 66 alive across generations.
...read more
read less