Wilmington Route 66 sign

Day 167: Route 66 and Chicago, Illinois

August 1, 2025

Our plan this morning was to arrive in Chicago towards the end of the day, and we'd be seeing quite a few roadside attractions on Historic Route 66 along the way. Our first stop was the town of Gardner to see the Two-Cell Jail, which was built in 1906 and closed in the 1950s. It was a local detention facility, rather than a hardened prison where people would stay long-term, and each cell has little more than a hard cot and bucket, with a small space for the guard's desk and a wood-burning stove.

Two-Cell Jail
Two-Cell Jail
Inside as you would expect is 2 cells
Inside as you would expect is 2 cells
There was a small diner next door
There was a small diner next door
The Shop on Route 66
The Shop on Route 66

Further along the road is another photo op: The Shop on Route 66, a bright red building that today has Coke memorabilia and other items. And about 12 miles north in the town of Wilmington, we stopped to get pics with the Gemini Giant, a tall 9 meter (30 feet) tall statue of a man clad in a green spacesuit, wearing an astronaut's helmet and holding a rocket ship in his hands. He was built in the 1960s and named after the Gemini space program from that decade. These "Muffler Men" fiberglass sculptures are very kitschy, but we love seeing them! There was also a Route 66 shield sign we could crawl into that specifically said we were in Wilmington.

Selfie with the Gemini Giant
Selfie with the Gemini Giant
Wilmington Route 66 sign
Wilmington Route 66 sign

The Town of Joliet

Along Historic Route 66 is the city of Joliet, which once had the second-largest steel mill in the country, and was an important economic and manufacturing hub in Illinois' history. We saw a replica of the Bluesmobile from the "Blues Brothers" movie atop a pole along Route 66 in Joliet (it's set in Chicago and its surroundings, although Lisette hasn't seen the movie so doesn't know much about it). The pole was in front of a couple of dumpsters though, so it didn't exactly make the best photo!

Blues Brothers police car
Blues Brothers police car

The Route 66 Park in Joliet told us more about the city's history, and we could see more Blues Brothers memorabilia, an 8-foot tall Steelman statue, a retro ice cream shop, and another shield sign noting that we were in Joliet.

Cafe at Route 66 Park in Joliet
Cafe at Route 66 Park in Joliet
Greetings from Joliet
Greetings from Joliet

Driving on, we didn't know who Jacob Henry was (we later learned he was a wealthy railroad magnate in the 1800s), but his legacy lives on at the Jacob Henry Mansion Estate, which is open for tours and is also rented out for weddings and other events. We didn't go inside, but it's a grand estate, and there are a lot of other historical mansions in the area that we liked looking at to get a glimpse of the glitz and extravagance of decades past.

Jacob Henry Mansion
Jacob Henry Mansion

Speaking of imposing buildings, the Old Joliet Prison Historic Site definitely claims that title in the city. It's an gigantic Gothic-style prison made of quarried limestone from Joliet, which opened in 1858 and only closed in 2002. Tours cost $20 during the day, and there are also nighttime tours that focus on the more haunted and dark history of the prison. We didn't do any of the tours, but did walk around the imposing structure, which has a lot of barbed wire wrapped around it as well, adding to the formidable look of the penitentiary (it definitely looks like a historical, hard labor prison). The prison was also used in the "Blues Brothers" movie and the TV series "Prison Break."

Old Joliet Prison
Old Joliet Prison
Looking inside the prison gates
Looking inside the prison gates

Burr Ridge

Continuing north, we arrived at the Harvester Park in the town of Burr Ridge. The park would make any kid happy--it has a water fountain area to skip around in and cool off in the heat, a musical area where kids can play a number of instruments (usually banging the drums and other instruments loudly and offbeat), a playground with slides and a small flying fox/zipline, and a number of Route 66 structures.

Michael with a mechanic at Harvester Park
Michael with a mechanic at Harvester Park
Lisette trying to pick off some of some Sheila fur
Lisette trying to pick off some of some Sheila fur

We enjoyed walking around with Sheila to explore the park and go on some of the rides (we tried one designed like a surfboard, and it was very hard to maintain our balance)! Sheila definitely had a ton of fun being outside and getting to sniff all the flowers and plants. The park was packed on the Friday afternoon we went, as kids are still wringing the last days of summer ahead of going back to school. Since it's summer, Sheila is shedding fur like crazy, and we used our time outdoors to pick at the never-ending amount of loose fur that is coming off her (it's a daily battle that we lose nowadays and our 4th roommate in the RV is definitely a big wad of her fur inside).

Cigars and Stripes BBQ Restaurant
Cigars and Stripes BBQ Restaurant
The guy on top was quite creepy looking
The guy on top was quite creepy looking

As we got closer to Chicago, we found two more Route 66 attractions. The first is a muffler man on top of the BBQ restaurant Cigars and Stripes, which also has a fun mural of Route 66, along with an alien waving inside its UFO. The second was a sculpture called Spindle, of 8 cars stacked together on a pole like a shish kebab. We were disappointed by the last one though, because we'd expected the cars to be true to size, but they were practically microscopic! The homes around here though were adorable, and it felt like we were thrown into some kind of American sitcom from 50 years ago, seeing all the brown brick homes.

Chicago and All That Jazz

Chicago, we made it! Our first stop, The Plant, is a collaborative community of small food businesses located in a renovated meatpacking facility. Since it's mostly a food production facility they're generally not open to the public, so it was simply a brief stop for us to see some of the sustainable foods and packaging being developed here, such as a new type of eco-friendly container for ice cream tubs purchased from supermarkets. Hopefully these sustainable alternatives will become readily available and accessible!

First tight squeeze under a bridge
First tight squeeze under a bridge
The Plant
The Plant
Cool bar inside the Plant building
Cool bar inside the Plant building
Brewery inside the Plant
Brewery inside the Plant

Driving the streets of Chicago was a bit stressful, with Michael navigating narrow and busy streets in the big city in our 30 foot RV. But we also got to drive through some gorgeous neighborhoods, with iconic old homes lined up along the thick, tree-lined avenues. We were wowed by neighborhoods like Ukrainian Village, with its red-brick, multi-story homes.

Chicago Dogs

We'd had a Chicago-style hot dog when we visited a couple of years ago, so we decided to have this for dinner. As a big city, there are SO MANY OPTIONS for where to get a hot dog, and we went to Flub A Dub Chub's (we also just loved the name), which also had a vegetarian option for Lisette. If you've never tried a Chicago dog, it's traditionally an all-beef hot dog in a poppy seed bun, topped with yellow mustard, sweet pickle relish, chopped white onions, tomato slices, a dill pickle spear, sport peppers, and celery salt. An absolute taboo is to add ketchup to a Chicago dog!

Flub A Dub Chubs hotdog
Flub A Dub Chubs hotdog
Lisette with her vege hotdog
Lisette with her vege hotdog

Fortunately, he found a place to stop around the corner for Lisette to order and pick up the hot dogs. Flub A Dub Chub's is on the lower ground level of a building and there's seating inside, as well as on the street. Inside, the restaurant's walls are filled with people's drawings of hot dogs--from the hot dog "Flubinator" (a play on the "Terminator" movie), Flubeyonce (hot dog singer, Beyonce), and many others, which mostly are a take on pop culture. It turns out that there's a monthly hot dog drawing contest, and people get to vote on the winner, who gets a prize (a t-shirt and a $20 gift voucher). The winner from the last month was a play on Sabrina Carpenter, the current 'it girl' in music.

The hot dogs we ordered were delicious! Lisette enjoyed her vegan (soy) hot dog (called The Willie), while Michael also liked his 1/4 pound hot dog with all the toppings (called The Chubby). So we basically ordered the Chubby Willie, with a side of fries!! While Chicagoans do not approve of ketchup on hot dog, we had half a dozen ketchup packets in our order for the fries, which was hilariously ironic.

Lincoln Park (and Parking)

There's very few options for an RV to park in a city like Chicago, and to make matters more challenging, we were there on the same weekend as Lollapalooza, a four-day music festival that happens every year in Chicago, which was expected to have over 400,000 people attending. We arrived in Chicago on a Friday night too, and the festival was from Thursday to Sunday, so we were right in the thick of a hectic weekend!

The one place we apparently could park and didn't have to pay a meter was at Lincoln Park (another place named after President Abraham Lincoln), which is the largest public park in Chicago and is the second most-visited city park in the country, after New York's Central Park. It has a nature boardwalk, a free zoo, and lots of greenery to go jogging, walking or running in, adjacent to Lake Michigan.

Our parking spot while in Chicago in Lincoln Park
Our parking spot while in Chicago in Lincoln Park

When we arrived the park was packed, as the weather was gorgeous and the curbs were lined with cars parked alongside them. Would it be possible that our big RV would find a spot?! But then...to our amazement, we found the ONE spot left that was perfect for us to fit in! And we could park for as long as we liked, because there were no signs saying anything to the contrary. Yay!!

Sunset walk in Lincoln Park
Sunset walk in Lincoln Park
Chicago skyline at night
Chicago skyline at night

In the evening, we walked around the nature boardwalk, which was wonderful except for the couple of rats that we saw darting ahead of us in the dusk. The first one scared Lisette enough, but after the second one, Lisette yelped, "Nope!" and reversed back the way we came from. We also stumbled upon a free movie screening of the classic movie, "The Princess Bride," which people were enjoying sitting out in the park, on blankets or camping chairs. Such a wonderful evening!

Princess Bride in the park
Princess Bride in the park

We were content to head back to our RV that evening, putting up our shades to block the park light. Of course, that didn't block the noise (lots of cars in particular zooming past throughout the night, with one blasting music where all we could hear was the "thud thud" of the bass at about 2am). It also didn't block out the smell, as someone was smoking what seemed like a lot of weed near us! Hopefully that helped us get a better night's sleep in some way!

Route Map

Near Pontiac to Chicago

Leave a Reply to Day 205-7: Atlanta, Georgia - Glassies on the Road Cancel reply

Your email address will not be published. Required fields are marked *

One comment on “Day 167: Route 66 and Chicago, Illinois”

Read the next journal entry
Don't stop now, here's another thrilling story from our adventures.