Day 2 – 3: Illinois, Chicago

Our first stop in Illinois, Chicago, is the beginning of Route 66. We get to spend a full day here before finally hitting the Mother Road…

DAY 2 PLAN:
ACTIVITY: Optional hike of Brandywine Falls or Ice Cave (Ledges Trail); or take the scenic railroad trip; or visit the beaver marsh
DEPART: Cuyahoga Valley National Park by noon
DRIVE: Cuyahoga Valley, OH to IN to Chicago, IL (estimated 350 miles / 6 hours straight driving), change timezone at IL state line
ARRIVE: Chicago, IL and check-in at the Travelodge Downtown Hotel (for 2 nights)

DAY 3 PLAN:
ACTIVITY: The Chicago Gangster Tour
ACTIVITY: Dinner and a Show at Tommy Gun’s Garage

RESOURCES: DAY 2 PLANNING PAGE | DAY 3 PLANNING PAGE | CHICAGO WEATHER

NOTES FROM THE ROAD: CHICAGO, A FIRST TASTE… (arriving in Chicago)

Not sure when we officially crossed into the “mid west,” but it was flat land and big sky, with easy open roads. We had exchanged woodland scenery for farms, and with the speed limit at 70mph, we made it to the outskirts of Chicago in good time. Approaching the city, the cluster of buildings that form Chicago’s skyline seemed to rise in a dramatic push up from the surrounding flat lands. Traffic thickened and we had to pay attention to the road signs again. … [ read more ]

NOTES FROM THE ROAD: CHICAGO EXPLORATIONS… (walking around Chicago)

Exploring the city, cameras in hand, we just enjoyed the urban feel. Though part of the mid-west, Chicago is an old industrial city similar in visual style to NYC. In fact, the skyscrapers we think of as so typically “New York,” were actually pioneered in Chicago. The Great Chicago Fire of 1871 had destroyed most of the city, so the skyline was re-defined from scratch in the 1880s, just as the “Chicago School” began designing buildings with steel-frame construction that used large areas of plate glass … [ read more ]

NOTES FROM THE ROAD: CHICAGO, HAVING FUN WITH HISTORY (1920s Gangster attractions)

With only one day to visit Chicago, it would be impossible to really discover much or even get a “feel” for the character of the city. We decided not to try. We would explore a theme instead. Considering a multitude of choices, we settled on being a bit playful and searched out the city’s roaring 20s gangster-era lore.Now, like every town, Chicago works hard to promote the positive — the beautiful, the artistic, the intellectual and cultural things their amazing city has to offer — so there is no official “Gangland Museum” or anything of the sort … [ read more ]

AMERICA THE BEAUTIFUL: PORTFOLIO: ON THE ROAD TO CHICAGO (images from the drive)

It took two days to reach Chicago. This part of the drive was mostly on the interstate, but as we approached the city, the skyline seemed to rise up out of the flatlands of the mid-west, beckoning us to a comforting urban environment that we would find somehow familiar. This portfolio contains a selection of imagery from the approach to Chicago. … [ read more ]

AMERICA THE BEAUTIFUL: PORTFOLIO: CHICAGO — THE CITY (images of the city)

Chicago is an eastern city at heart. Built upwards, instead of out, with skyscrapers defining its skyline, it reminds us a lot of New York. We are comfortable in this gritty urban landscape, where lines are predominantly vertical, and light and shadow play off architectural cues creating a photographic paradise. This portfolio contains a selection of imagery from the Chicago cityscape. … [ read more ]

AMERICA THE BEAUTIFUL: PORTFOLIO: CHICAGO GANGSTER FUN (images from 1920s gangster themed attractions)

Some quirky fun on the 1920s gangster theme in Chicago. Spent a day with the gang from The Untouchable Gangster Tour, followed by an evening at Tommy Gun’s Garage. Great fun was had by all. This portfolio contains a selection of imagery from the gangster prohibition-era themed attractions … [ read more ]

PRACTICAL MATTERS: PLANNING ONE DAY IN A CITY (tips on planning)

One of the biggest challenges we faced on our trip was the lack of time to really “take in” any one place. Of course, we knew that would be the case when we decided to do such an intense road trip, but we still wanted to make the most of our stopovers. Cities were especially difficult. What was the point in visiting a city for just one day — what could we possibly discover in such a short time? … [ read more ]

REFLECTIONS & OTHER THINGS: TOMMY GUN’S GARAGE(dinner and show review)

Tommy Gun’s Garage is a “Roaring 20’s”-themed dinner theatre venue that recreates the “speakeasy” atmosphere centered around a musical-comedy review. It’s a brilliantly simple concept: the whole place is the “stage” and everyone is part of the show. From the moment you arrive outside, the experience begins as “Gloves,” the “gangster” at the door, demands the password … [ read more ]

REFLECTIONS & OTHER THINGS: THE UNTOUCHABLES GANGSTER TOUR(tour review)

The Untouchable’s “Gangster Tour of Chicago” is a quirky 2-hour “live action” tour offering visitors an amusing take on the city’s Prohibition-era history and the gangsters that animated it. With costumed tour-guide-actors and a bit of cheesy comedy, the experience can be enjoyable — and you may even learn a thing or two… [ read more ]

REFLECTIONS & OTHER THINGS: FRAGMENTS FROM THE ROAD TO CHICAGO (thoughts on the trip thus far)

Two days on the road so far, and we’ve already crossed several states — from NY to Chicago. Pennsylvania seemed endless yesterday. Luckily we were well rewarded in the evening. Our campsite was very beautiful, on the banks of the Cuyahoga River, not far from a cascading waterfall. Freshly cut, like a crop circle, into the tall grass that almost served as “walls,” the site was perfect, and we got the tent up in no time. Then the familiar pleasure of the fire… [ read more ]

ILLINOIS THINGS WE LIKE:
The Untouchables Gangster Tour, a fun bus tour of Chicago’s gangland past…
Tommy Gun’s Garage, dinner and a roaring 20s spectacle in a “speakeasy”….
Millennium Park, for the Cloud Gate sculpture of course …