This Segment: Chicago, Illinois to St. Louis, Missouri
Next Segment: St. Louis, Missouri to Oklahoma City, Oklahoma
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When I was young, we road-tripped across the western United States, and most parts of Route 66 from Santa Monica, California to Albuquerque, New Mexico. My parents had been talking for years about finishing the rest of the "Mother Road" - in August of 2022, we had a chance to go and it was EPIC! In these videos, we will share our experiences as well as some practice tips to get the most out of a Route 66 trip.

On this segment, we flew to Chicago, Illinois, and drove to St. Louis, Missouri. We started at "The Bean" downtown Chicago, and a couple hours of traffic later, we were in the countryside. We passed through many small towns that were well preserved - towns like Dwight, Illinois I wish we had more time to enjoy them. We were running low on time during our first day so we didn't get to visit many places that were open, but they were still wonderful to explore (such as Pontiac, Illinois). My dad also suggested a short "detour" to see the factory where @Rivian is producing electric trucks.

Springfield and the historical sites for Abraham Lincoln cannot be missed. The National Historic Site not only includes tours of the inside of Lincoln's house, but has a couple blocks of period-correct houses that are fun to explore. You can see the only house he ever purchased - he lived there from 1844 to 1861. It was donated by his son to the State of Illinois as long as they agreed to take care of it, and never charge to visit. The Old State Capitol, where Lincoln gave his famous "house divided" speech can be visited for free, with a suggested donation. His law office and Presidential Library and Museum are close as well. All of these sites are within walking distance - we found parking to be free and close-by. Spend at least an entire day seeing these places if possible.

As you drive, many parts of the original Route 66 are visible outside of the main cities - some towns have turned this into a park space or a bike path. Either way, seeing the various unrestored segments was very neat. Throughout most of Illinois, Route 66 divides as you enter each town: take the 1926 original segment that goes straight through the center of town, or take the (generally) 1937 / newer segment that skirts the town to the north. We mostly went on the older route when time allowed.

Coming into the East St. Louis, there is a Lewis and Clark park that we wish that we visited, but skipped to make our hotel at a reasonable time that night. We first decided to visit Cahokia Mounds State Historic Site then the Chain of Rocks Bridge. Getting to the Bridge was quite interesting, but gave a spectacular view of both the Mississippi as well as the canal and locks. The Cahokia Mounds interpretive center is closed, but the Mounds can be hiked. Please stay on the trail and be respectful of the space.

The Chain of Rocks Bridge carried cars across the Mississippi River from 1929 to 1970 and is now a walking bridge. It was almost demolished, but a local hiking group saved and it reopened in 1998. This bridge features a unique 22 degree bend near the middle, and two pumping station islands you can see for the St. Louis waterworks - built in the early 1890s and 1910s. The views were great and it's fun to walk into another state!

Must-see places on this segment:
-The start of Route 66 on the corner of Michigan Ave & E Adams St.
-"The Bean" and walk around Millennium Park
-Dwight, Illinois / Ambler's Texaco Gas Station
-Odell, Illinois / Standard Oil Gas Station
-Segments of the old pavement (seen various places throughout)
-Pontiac, Illinois
-Normal, Illinois / Sprague's Super Service Station / Rivian Factory
-Springfield, Illinois / Lincoln Home National Historic Site / The Old State Capitol / Lincoln Presidential Library and Museum / Lincoln's law office / Lincoln's grave
-Litchfield, Illinois (to eat)
-Soulsby Service Station
-Cahokia Mounds
-Chain of Rocks Bridge

Tips on this segment:
-If you fly into O'Hare International Airport, give yourself some extra time to find the train to the rental car facility. The train is fast and travels frequently, but was difficult to find the station.
-Starting downtown Chicago is a must. There is secure parking right below The Bean that gives easy access to the official start on the corner of Michigan Ave & E Adams St. Walk around the park, get some street food, see some sights before heading out.
-We would likely skip the Route through most of Chicago. The road was rough and there was a lot of traffic. We advise driving the fastest route to Joliet, Illinois, and "start" there.
-Stay in one of the small towns in rural Illinois. There are lots to choose from!
-Visit the Chain of Rocks Bridge around sunset and give yourself time to walk across it into Missouri. As of summer of 2022, the Missouri side is closed, however.

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