Hey there, time traveller!
This article was published 12/8/2017 (829 days ago), so information in it may no longer be current.
It was not the first time I visited Chicago, but on this trip, only three weeks ago, it would be the first occasion in which my visit was not about business, but rather to just experience the city from a tourist perspective.
For the better part of four days I, with the small group I travelled with, was determined to capture as much of the essence of this third-largest city in the United States as possible.
While we took in all nature of events and activities, in the end I was surprised at just how much of a historical tour we had created out of our pub stops, restaurant choices, and places we paused to spend time at.
Most major cities offer bus tours that provide an excellent outline of the regions and sites that are most interesting. In this instance, because of the canal system around which so much of Chicago’s growth was built, we took the boat option, known as the Architecture River Cruise, on board the Chicago’s First Lady vessel (cruisechicago.com).
The moderators on this boat are all volunteers from the Chicago Architecture Foundation. They do an exceptional job of bringing the history of Chicago to life, highlighting how each era came with an entirely different design component that defined, not just the times, but the nature of the people who lived and worked there.
From the Montgomery Ward’s warehouse, home of the first mail-order catalogue building in North America — now a Groupon headquarters — to Donald Trump’s more recent homage to himself on North Wabash Avenue, this tour really provided a history of the structural foundations, mirroring the growth of this great city.
If you like a few ribs with your history, you may want to follow us to the Twin Anchors BBQ restaurant in the Old Town section of Chicago. While the building was erected in 1881, it was 1932 when it became the home of the Twin Anchors, becoming one of the early speakeasy taverns, as they were known then, during the years of prohibition in the United States (twinanchorsribs.com).
Its quality food later made it a must go place for local residents and celebrities. In the 1950s, it became one of Frank Sinatra’s favourite haunts, and from the photos and letters posted on the walls, it is still a place you can meet international celebrities. It was one of the locations featured on Boardwalk Empire’s Speakeasy Tour documentary.
This would also be the beginning of our History on Tap tour (historyontap.com) we took with Liz Garibay, who markets herself as a beer and tavern historian. "Alcohol is a lubricant for history," she would say. So naturally we had to sample a brew at each of the historic bars she stopped at during our tour, including Marge’s Still, "the oldest continuing running tavern in Chicago"(margeschicago.com).
But the tour was about more than pints of brew and good food. Garibay also enlightened us on some of the history relating to the Great Chicago Fire of 1871, which destroyed more than a third of the city, and left over 100,000 people homeless.
She showed us some of the almost cardboard box size homes that were provided to the victims afterward, just so they would have some place to live as the rebuilding of Chicago began.
After a relaxing breakfast at the downtown AC Marriott Hotel where we were staying, we were close enough to walk to one of the stops for the Big Bus Tour, which circles around the major downtown attractions (bigbustours.com/en/chicago/chicago-bus-tours).
Once you purchase your day ticket, you can hop on and off the bus to spend extra time at those attractions that interest you most. There is a tour guide on board these double-decker vehicles to provide interesting highlights of the city as you pass them by.
Chicago was once the organized crime city of the United States, where civic officials were often accused of taking bribes. As our guide informed us, considering the last three governors of the state went to jail for illegal activities while in office, perhaps not all that much has changed.
Continuing what was becoming a history tour of Chicago, we got off the Big Bus near the location of the oldest Italian Restaurant in Chicago. The Italian Village opened in 1927, and has been run by the same family over three generations since.
Like Twin Anchors’, the walls are adorned with photos of celebrities who made it their dining choice over the past 90 years. Set off to the side, near the back of the restaurant, is a private area that was for the exclusive use of Al Capone and his associates during his criminal empire’s reign over Chicago.
It is conceivable that in its day, patrons of the 1921 built Chicago Theatre, only a few short blocks away, dined first at the Italian Village. The Theatre has been brought back to its original look and is still an active entertainment venue worth seeing.
The role of writers and authors in recording, and making history, cannot be overestimated. The National American Writer’s Museum has preserved the legacy of these historians for today’s, and future generations (americanwritersmuseum.org).
The museum highlights writers from all genres — from Mark Twain to Bob Dylan, and from biographical novels to children’s books.
One of the entertaining interactive options is trying, and watching others, in the often frustrating and futile attempt to create sentences on an old-fashioned typewriter. Many of the younger, computer-savvy visitors had never seen such a unit before.
Specializing in serving organic vegetables, fruits and herbs grown in its own 3,000-square-foot rooftop garden, we closed the day with another great meal at Homestead on the Roof on Chicago Avenue. (homesteadontheroof.com)
It is only the end of day two, and I already feel like I need a holiday from the holiday. But there was much more to come.
Chicago truly is an amazing culinary city. So we start the second half of our stay with brunch at the highly recommended Bar Pastoral (pastoralartisan.com/barpastoral).
Most of the brunch plates are large, but by the rave ratings on review websites, we knew we must order the Gruyère Scones.
Hungry hands reach for them time and again, until they are all gone. Fully satiated, our next adventure was a welcome one — and something I would never take the time to experience on a business trip.
At Monroe Harbor, we board a six-person charter to view Chicago’s skyline and the Lake Michigan shores for a couple of hours of absolutely relaxing sailing.
On the 36-foot Catalina sailboat Bernard, captained by Mike Blanchard, we learn about how the lakeshore was used so effectively for the Chicago World’s Fair of 1893, and saw how it has become a magical place of relaxation and activity for residents and tourists alike today (www.comesailing.us/).
After disembarking the Bernard, my heart began to thump a little faster in anticipation of our next activity. I have never ridden on a Segway, and was not sure I wanted to join the rest of the group on this part of the journey. But courage prevailed, and I am glad it did.
The company, Absolutely Chicago Segway Tours, goes to extremes to make sure its guests are trained and ready to ride safely (http://chicagosegways.com).
First, they showed us an excellent training video. They also have their own training facility of sorts in a tunnel near the lakeshore touring area. The guide helps each person get used to operating the Segway, and helps with the initial underground practise sessions before letting us go practise on our own to gain confidence, while still in the tunnel.
By the time we started the tour, I found this mode of travel enjoyable and exciting. It was extremely informative as well, since our guide stopped frequently to make sure we were doing well, as he educated us on some of the highlights of the city before us.
While monstrous skyscrapers may appear to be the signature feature for downtown Chicago, the city should also be recognized for its exceptional parks and play areas, most of which are punctuated with dramatic versions of public art.
After our Segway experience, we strolled over to nearby Millennium Park — one of the most recently opened public areas — where there are loads of dramatic art installations, as well as activity options for people of all ages.
Of these, one of the most visited and photographed for its uniqueness, is officially labelled Cloud Gate. But it is more commonly referred to as "the bean", because of its legume-like shape. At 10-by-20-by-13 metres, it is a massive and imposing reflective steel structure, which attracts most who visit the park to have a photo taken of themselves in some manner under, or against, its mirror effect.
On our last day, our group split up, with each going more or less separate ways to shop, or take in some of the other attractions that interested them the most.
At about $135, the Chicago City Pass allows entry into a number of the city’s major attractions, at significant savings over individual entry prices (citypass.com/chicago).
Some took in the Shedd Aquarium, others went to the Museum of Science and Industry, and others to the Art Institute of Chicago, just three of the options with the pass.
We closed out our stay with dinner at The Safehouse, a unique spy-themed restaurant and bar, where guests are interrogated for a password before they are allowed entry.
Once inside, there is a potpourri of real spy information and mission impossible games for guests to participate in (www.safehousechicago.com).
While we really enjoyed the creativity of this restaurant, with "Chicago’s Best Burgers" being a part of its tagline, it is a culinary option clearly targeted to family visitors.
Its Camp X Poutine, a specialty they say "comes straight from the Canadian spy training center", is a serving of French fries, loaded with white cheddar cheese curds, Portobello mushroom gravy, and topped with a fried egg. We shared an order and could not finish the heap of calorie-laden dish.
Four days seemed to go by very quickly. I feel like we still missed so many of this amazing city"s attractions. While this was very much a trip through Chicago’s past, I look forward to returning to see more in the future.
Read Ron’s blog at thattravelguy.ca Listen to Ron’s latest podcasts via his website, or on demand on iTunes.
Ron is a dedicated traveller, having explored 65 countries around the world as well as all but one province in Canada (Newfoundland).