May 14 & 15 2012, Chicago

A flight of just two hours got us here from New Orleans yesterday around 2.30pm and we checked into the Drake Hotel, at the north end of Michigan Avenue overlooking Lake Shore Drive. We have a room overlooking the beach on Lake Michigan, just north of the hotel...

The view from our window in the Drake Hotel.

After settling in, we went for a walk down to the Chicago River and back, with a coffee stop at the John Hancock Centre and then relaxed in our room for a couple of hours before being really lazy and going down to the hotel bar (which is apparently unchanged since it opened immediately after the repeal of prohibition) for a drink and a light supper.

Today, Tuesday, we began by buying tickets for the city bus tour, but soon realised that the tour is operated on both double decker buses and smaller vehicles that they call trolley cars. The first of these to turn up at our bus stop was a trolley car, so we boarded, only to find that the wretched thing was terribly uncomfortable (there was nowhere near enough leg room for me) and the driver was a useless tour guide. Despite the fact that driving while operating a mobile phone is illegal here, he drove this thing around with one hand on the steering wheel and the other holding a conventional microphone into which he gave intermittent bursts of uninformative drivel along the lines of, "Ok guys, this area on the left here is a place where you can find lots of restaurants, so if you're looking for somewhere to eat and you come to this area on the left here, you'll find lots of restaurants. So that's the restaurant area here on the left, and in this restaurant area here on the left you'll find what many people think is the best restaurant in Chicago, right over here on the left." (Pointing to a hot dog joint!).

Jenny and I therefore got off at the first stop and checked with the tour rep manning the kerbside booth to make sure there was a double decker bus coming soon. He made a call on his walkie-talkie and assured us that there would be a double decker coming along in about 20 minutes. While we were waiting, a single decker black vintage coach pulled up, emblazoned with the logo "Chicago Gangster Tours". Before we left England I had tried on a couple of occasions to search the net for exactly this sort of thing, thinking that in a city which is so famous for gangster activity in the 1920s and 1930s there was sure to be a gangster tour, but I couldn't find any. We seized the opportunity (our city bus tickets will still be good for tomorrow) and jumped aboard to spend an entertaining 90 minutes or so. The driver ("Shoulders") and his sidekick ("Three Knives"), both dressed gangster style, took us around to see the sites associated with the gangster era, although sadly, many of the locations have changed beyond recognition. Here are a couple of interesting examples, though...

This is the Biograph Theatre, exactly as it was, where John Dillinger was lured by his girlfriend, Anna Sage, in 1934 following a deal she did with the Feds to give him up in exchange for the $20,000 reward and a promise that she would not be deported (she was Romanian). As they left the theatre, he saw the agents and tried to run, but was gunned down and killed in an alleyway a few yards away.

This is the site of the garage where the St Valentine's Day massacre took place in 1929. The pathway to the right of the picture marks the line of the north wall of the garage, against which seven gangsters were lined up by rival gang members dressed as police officers and machine-gunned to death. The assassins were working for Al Capone, with instructions to do anything to kill Bugs Moran, and they mistakenly believed that Moran was one of the seven, but his chauffeur had been late picking him up that day and so he survived.

Following the gangster tour, we had one of our coffee stops and then went to the river to catch a 90-minute cruise, guided by a lady who talked about the architecture of Chicago. It was a most interesting trip, although temperatures were in the low 80s by this time and Jen disappeared to the air-conditioned lower deck about half-way through. I, on the other hand, have a very nice sun-hat which doesn't make me look too much like Benny Hill, and so I stuck it out!

The L crossing the Chicago River.

This huge Art Deco edifice, known as Merchandise Mart, cost $80 million dollars to build in the 1920s, but was not a commercial success and was bought later by Joe Kennedy (JFK's father) for only $13 million. The Kennedy family sold the building in the late 1990s for somewhere north of $500 million!

On the way back to the hotel we called in at the John Hancock Centre (sorry - Center) to take in the views from the observation deck on the 94th (I think) floor.

Part of the Chicago skyline, with Lake Michigan beyond, looking south from the observation deck of the John Hancock Building.

Not yet sure what we're doing for supper tonight, so will report back tomorrow.

Jen's bit: The hat does make him look like Benny Hill. Jx