I travel back in time a bit, to a different year, and just to warm things up, a different season. And just as well, cause Chicago is a perfectly avoidable city during the winter months! In summer, however, it’s a very different story.

Having already attended the ‘Indian’ version of Utsav’s wedding early in ’07, it was only befitting that I attended the ‘American’ one. Besides, Chicago had long been on my list and this was the perfect opportunity.

A cheap air fare ($139 return all incl) meant a very early start for me as my flight was out of Islip Macarthur Airport in Long Island – essentially the boondocks! That also meant that I would miss out on the much storied Chicago O’Hare! Instead, I had to make do with Chicago Midway and to this day I am unable to discern why it is named so.

On arrival, I was all psyched about using the public transit system there – one of the few cities in the US (outside of NYC) that can genuinely claim to have one. Chicago Transit Authority’s (CTA) Orange Line didn’t disappoint. Within minutes, I was in downtown Chicago and a short while later, looking out of Bhavjit’s cousins condo – where we would be bunking for the weekend.

A spacious downtown condo in a fully serviced building with all those sports facilities – all at a fraction of the cost of NYC. I had already begun liking the city!

The wedding was some distance away from Chicago and after a full day’s worth of merriment, we got back pretty late in the evening. Bhavjit still had some pep left over and decided to go out with his cousin. Being on the other side of 30, I was pretty knackered by then so decided to turn in instead! Meanwhile, the bright city lights beckoned for a shot out the window and I, of course, obliged!

In the morning, while the boys snored away to glory, I got myself a head start. Having only a day to explore the city, there was no time to waste. A brisk walk east, a little over a mile down Illinois St and I was at the Navy Pier – one of the city’s biggest landmarks. So much for making an early start – the place was already teeming with tourists!

Located on Lake Michigan and aptly termed Chicago’s ‘lakefront playground’, the Pier is touted as the Midwest’s most popular tourist attraction and true to its reputation, has it all – shopping, dining, entertainment, rides (which include A McDonald’s sponsored Ferris Wheel!), boat tours and cruises and even a Budweiser sponsored Beer Garden (Yuck!). It’s the kind of place where locals would rather not hang out. The kind of place that is avoided by most but for a first time tourist (like myself), blasphemous, if missed! A Times Square if you will. And so I went along with the flow…

But to be fair to the place, it’s not half as bad as I’ve made it out to be – crowded and touristy, yes, but spanking clean and well maintained to and with an area covering almost 50 acres, there is no shortage of things to amuse one with. And if you brave the crowds and walk the mile long Pier to its very end, the views of Lake Michigan are truly rewarding.

I had always heard tales about how massive the lake is but you really have to see it and experience it for yourself to appreciate its size. With ocean like proportions, it is this large water body that gives the city a lot of its character.

As you’ve guessed by now, Chicago is very much an outdoor city in the summers. People turn out in large numbers -some on yachts, others on cycles, some on roller blades and others simply on foot. A lot of them exercise nuts, some just soaking in the sun. Despite these large numbers, the city, miraculously, seems to provide for everyone. Chicago abounds in parks and trails and more than anything, a beautifully developed lakefront which caters to many but where everyone manages to find their own spot.

If the lake is a beehive of activity, the river isn’t far behind. It is amazing to see how beautifully the river blends into the very heart of downtown Chicago and to me that is one of the most charming facets of the city.

The river is most notable for the 19th century civil engineering works which reversed its flow – away from Lake Michigan. This was done for sanitary reasons and up unto that point, locals referred to it as ‘the Stinking River’. The river is also well known for the local custom of dyeing it green on St.Patrick’s Day.

Today, the Chicago River is spanned by 38 movable bridges, some of them dating back to the early 19th century. The waterways are busy with recreational traffic which ranges from luxury yachts to sail boats to kayaks to water scooters and of course the many Tour Boats and Charters that ply there. Cafes, bars and a promenade line the riverfront in most parts and a viable way of getting from one point to another is the Chicago Water Taxi which makes scheduled stops at many of these.

The Lake and the River had already impressed me enough and now, as I headed south along Lake Shore Drive, it was the city’s famed architecture that caught my attention. Chicago boasts a skyline, second only to the Big Apple and elegantly balances the old with the new. Much like the twins were in NYC, Chicago’s Sears Towers are a city icon and can easily be identified from miles away – towering over the skyline. My bias has always been towards older structures though but it is difficult to ignore the newer ones in Chicago – each standing out for its own strong sense of design.

And what sets them apart from those in NYC is, quite simply, there upkeep! I don’t know if NYCs buildings have simply aged or are just the victims of old tenancy laws, but when it comes to making a good building look great, Chicago seems to have got it right!

A 2 mile walk along the lake and I finally reached Buckingham Fountains – highly recommended by a friend. The fountains are humongous – easily the largest I’ve seen in a while. With the Lake on one side and the skyline on the other, the setting is truly wonderful and the long trek there seemed worthwhile!

I had walked close to 5 miles by then and in all my enthusiasm, skipped breakfast! The heat and humidity was telling on me and I urgently needed a pit stop. I stumbled across a really nice sandwich place on Wabash Ave aptly called ‘Potbelly Sandwich Works‘ which I was told later is a small chain. Highly recommended! And they do take their business very seriously!

Last but not the least, it was Chicago’s Transit System (or El as its better known) that easily stole my affections! Chicago is the only other city in the US, outside of New York, that can boast of a 24 hr transit system (even though limited to a few lines). And just like the city’s buildings, streets and sidewalks, the CTA’s trains and stations are impeccably clean and well maintained. With 60% of its 100 mile plus route mileage elevated (hence the nick name El), the transit system is possibly the cheapest and best way to see the city. And for a rail fan like myself, a seat up front, is a HUGE plus!

I’m still to check off San Francisco, Seattle, Miami and New Orleans from my list. If and when I do, the order could quite easily change. But this short visit was convincing enough to make Chicago narrowly pip Boston to second place! No marks for guessing the Numero Uno 😉