The Road Starts Here: Route 66 in Chicago, IL

September 11, 2026

We recently visited Windy City and of course had to visit a couple of iconic Route 66 locations. The big thing we couldn’t miss was the sign for the beginning of Route 66 right outside the famous Art Institute of Chicago. Depending on the time of year you go, the main sign might be easy to miss — walk across the street from the museum straight out from its front doors, and it will be directly on your right. We went during a busy tourist season while there were several fun events at Millennium Park, so we almost walked right passed it trying to swim through the crowd.

After you’ve taken a few goofy photos, head right into the Art Institute of Chicago. Anyone will tell you it’s a must-see if you’re visiting. Not only do they have some of the most famous paintings in the world, from Vincent Van Gogh’s self-portrait to Edward Hopper’s Nighthawks, but they have a delicious cafe and tons of windows that let you see Millennium Park and the gorgeous Chicago downtown. If you’re short on time, a large section of their map leads you directly to their most beloved and famous works so you can dip in and be back on the road in an hour.

While you’re visiting, don’t miss some of those classic touristy spots like the Shedd Aquarium. We spent a lot of time wandering the large circular building and finding our favorite fish, but the best part of the experience was finding the center. Not knowing what we walked into, we sat down on surprisingly comfy concrete stands and watched a short video about the aquarium’s conservation work. Then, they brought out the star of the show — a sea lion named Cruz! Cruz was shot by commercial fisherman and was found by conservationists with wounds in his face and eyes, and is permanently blind. However, his lack of vision didn’t slow him down — using his whiskers and keen sense of hearing, he shook fins with his handler, barked, balanced on one fin, and waved to the audience. It was one of the most memorable parts of the trip!

We also caught an architecture boat tour that goes through the river downtown with Shoreline Sightseeing — our guide was tons of fun and chock full of fun facts about the iconic Chicago skyline. The boat had a bar with water and alcoholic drinks in the back, as well as bathrooms, which are needed if you’re trying to stay hydrated like we were. Just make sure to bring sunscreen!

We bought a CityPASS, which is a bundle of 3 to 5 attractions that saves you tons of money you may be paying otherwise for individual tickets, especially if you’re roadtripping with family. This isn’t a sponsored shoutout, so you know it’s a good deal.

In between all the excitement, we got a chance to see the vibrant sign for the Berghoff, a historic German restaurant that opened in 1898 and got Chicago’s first post-prohibition liquor licence (which is still on display inside). We didn’t have time to stop and eat at the time, but a few of the people we met highly recommended their bratwurst and German-style gnocchi.