Route 66. What to see between Bloomington & Chicago

Today you arrive in Chicago!! You are finishing US Route 66 with this final stretch, from Bloomington to Chicago!!! You have driven a lot of miles. There were two feelings for me this day.

On the one hand, I was eager to reach my final destination. But, on the other hand, I was feeling pity because these were the final steps of an intense and great trip.

Chicago Skyline, USA

From Bloomington to Chicago (or vice versa)

We start in Bloomington, 135 miles from Chicago. Getting to Chicago will take relatively little time, although there are still some things to do.

To take Route 66 in Bloomington, you must take Sherbourne Dr and go straight ahead.

The continuation of Shelbourne Dr is Route 66. Keep going through Lexington and Pontiac until you reach Odell.

Odell, what to visit?

In Odell, you have the “Odell Standard Station,” which was built in 1930. In 1999 the city bought it to restore it and now it is in very good condition. Then, finally, we pass by Dwight, where still stand buildings created by the famous architect Frank Lloyd Wright.

Route 66. Stretch from St Louis to Bloomington

Just after Dwight, the route splits. The first way is directed towards Plainfield, and the second one is directed towards Joliet. We took the second one because we found it more interesting. The first town is Wilmington; here is the “Gemini Giant.”

Wilmington and the Gemini Giant

The “Gemini Giant” is one of the giant’s classics that were placed along many roads and highways in the United States, including, of course, Route 66.

They are about 20 feet high and often have a hand with the palm up and the other palm down to hold some kind of tool or item.

They were known as the “Muffler Man” because usually, they were placed in front of auto cars holding a Muffler.

In the case of the Gemini Giant, you’ll see that it holds a rocket in its hands and wears a helmet.

This is because it was redesigned to advertise the “Launching Pad,” a cafe just in front of it. The redesign was to turn it into a kind of astronaut with a rocket in his hands.

We leave Wilmington behind and drive to Joliet, known as “The City of Spires,” because of the large number of churches in the area which have Spires.

Joliet, Route 66

In Joliet, you have the Rialto Square Theatre (102 N. Chicago Street), a luxury theater built in 1925. It was known as “The Jewel of Joliet,” and its decoration is pretty baroque.

You also have a museum of Route 66 (204 N. Ottawa Street) and of course “The Old Joliet Prison” (1125 Collins Street), the same that appears in the movie “The Blues Brothers” and the television series “Prison Break.” Unfortunately, the entrance is not allowed for now.

Now you’re getting closer to the suburbs of Chicago; you begin to notice that you are near one of the major US cities.

Chicago, Fer


But before you dive into Chicago, I recommend a final stop, Romeoville, where you can see The White Fence Farm. It is a pretty big restaurant/complex specialized in chicken dinners that started operating in 1920.

It has a giant chicken in front of the entrance, and inside there’s a museum of vintage cars and a small zoo, among other things.

Arriving in Chicago

And, gentlemen, we are in Chicago. Undoubtedly, Chicago has two characteristic points of Route 66 where travelers beginning their journey went to breakfast or lunch.

The first is Lou Mitchell’s, a place especially for breakfast, well-known since most travelers had breakfast here first.

The second one is Pizzeria Uno, who invented the “Deep-dish pizza,” which became the “Chicago style” pizza.


Where is the official start of Route 66 in Chicago?

There is a point where you have to go, E Adams St between S Michigan & Wabash Ave; what’s there, Fernando? You should ask. Well, just there is the sign that indicates you have just got to the point where Route 66 begins.

It’s your final destination; you’ve been chasing this sign for the last 15 days !. Congrats, you’ve arrived.

You’ve got all afternoon to explore the city of Chicago. My recommendation, check in at the hotel first so you don’t have to carry everything around the downtown and you can just wander. You don’t have any specific place to go today.

I recommend you to go to the Willis Tower this night and get on floor 103. It is called “The SkyDeck,” and you can see Chicago at night. It’s amazing. You can also do it tomorrow if today is not a good day.

But if you want, I can recommend some things you can do tonight, given that tomorrow you would like to visit Chicago.

Check out this Gangsters Guided Tour

Bloomington - Chicago, Ruta 66, USA

You can give a good walkthrough of Millenium Park. It is a pretty nice park. It is the one with the famous bean-shaped stainless steel sculpture called “The Cloud Gate.” Millennium Park is a 10-hectare park that always has activities, cultural exhibitions, events, concerts …

It also has an outdoor theater, Roman-style but modern, of course. Within Millenium Park, the Lurie Garden is representing the four seasons, is very nice. You can also visit it tomorrow if you don’t want to go today.

You can also visit Grant Park, which is much bigger than Millenium Park, about 120 hectares, and is right next. It has many sculptures and cultural activities and is one of the cultural centers of the city. I like a lot the Agora sculpture. There are like half-bodies that seem to be walking.

I leave you to rest because tomorrow you will have a busy day. Any suggestions? Any questions? You know, write us, and we will always answer.


“Travel is fatal to prejudice, bigotry, and narrow-mindedness.” – Mark Twain

US Route 66 Itinerary day by day

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Last Updated on 5 July, 2021 by Veronica

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