My desire to visit the much-acclaimed Chicago was an itch I had been dying to scratch for quite some time.  Several years ago, I forged a friendship with a number of colleagues while working for a client in Long Island.  Several days a week, we would have team dinners and play tennis; we even managed to score Knicks tickets at some point.  I look back fondly on that project.  It was a good project which yielded equally good company.  But I digress…  Many of my colleagues there were actually based out of our Chicago office and would travel in from the windy city each week.  Aside from the nightmarish winter stories they told, all of them seemed to adore the city and openly gushed about how great it was just about any chance they had.  As the project came to a close, I was extended warm and open invitations from a bunch of them to visit anytime.  Check that…Anytime but winter. 

As we all went our separate ways, one colleague in particular named Manish, whom I had become especially close with would reach out to me every 3 – 6 months to see when I was planning to visit.  Each time I would offer up a deep sigh wrapped in a polite decline.  I even had a few tentative travel dates set up, but it just seemed life kept getting in the way.  Was this trip ever going to happen? 

Several months ago I was staffed on a new project which would take me to Detroit.  Not exactly the exotic location one hopes for when you’re on a travel assignment.  Don’t get me wrong, Detroit has its own unique charm, but it’s not exactly the rust belt gem it was in its heyday.  The one bright spot…It’s only a stone’s throw away from Chicago.  Here was my chance!  No more excuses.

Ring, ring, ring. 

Manish:  Hello? 

Me:  I’m on a project in Detroit.  Can I come visit you one weekend in Chicago? 

Manish:  Absolutely.  It would be great to have you.

Me:  Cool.  I’ll book a flight tomorrow. 

That is just the kind of guy Manish is.  It had been well over two years since I had seen him, and it’s not like we talk everyday.  And here I was calling him out of the blue to impose myself, and there was no hint of hesitation to welcome me into his home.  My plan was falling into place … or so I thought.

Three weeks later my project was abruptly put on hold due to the client’s financial constraints, and I was forced to cancel all of my flight plans immediately, including my trip to Chicago!  Wow…Are you kidding me?  You just can’t make this stuff up.  The following week I was consumed with new business development activities to find my next gig.  There was no telling where my next project would land me, but I was still determined to visit Manish on the originally planned weekend.  So I rebooked my flight for an early departure on Friday, July 24th with a late return flight on Sunday, July 26th.  A few days after booking, I landed a new project in Manhattan which I would be starting the same week as my trip.  I got approval for the day off, which worked out, but I was a little concerned about how late I’d be getting home Sunday night.  It would be the night before my first full week of work at a new client!  Oh well, it didn’t matter at this point as the wheels were in motion.  The journey had to happen and if it meant a little exhaustion on a Monday morning, then so be it.  Chicago, here I come …

Friday  
After a slight delay out of my very ironic connecting flight in Detroit, I landed in O’Hare International around 10:30am.  I then took the extremely convenient CTA blue line train into the heart of the city.  I got to Manish’s place around noon, where I was greeted by a hearty handshake and warm embrace.  I instantly felt at home.  The location was sublime, and the building honestly felt like a high-end hotel.  Really, I’m not spewing hyperbole here.  There was an ultra impressive concierge service, gym (with a built in basketball court), library (extensive book collection), movie room (with traditional pop-corn cart that serves up goodies every evening), pool, spa, etc.  I’ve actually stayed in more than a few prestigious hotels over the years that would offer only a fraction of the amenities Manish’s bachelor pad touted.  Not too shabby, buddy!

I would be going solo for most of the day as Manish had flown in from Los Angeles that morning and would be working remotely most of the day.  So we grabbed a bite to eat at Chipotle for lunch, caught up on life stuff and discussed the plans for the weekend.  We had our game plan set, so off I went to do some sight-seeing while he got back to work.  

I’ve always felt the best way to explore a new place is to walk everywhere to soak up the atmosphere.  Avoid public transportation whenever possible.  The weather was flawless, so I made my way down the Magnificent Mile.  I was immediately drawn in by the imposing style of architecture that the city had to offer.  What I found to be most impressive was the skillful balance of open space and dramatic skyline.  Every building just seemed to meld into its surroundings as if it had always been there.  I must say, it was pretty inspiring. 

I spent most of the day in Millennium Park taking in the great energy.  The iconic Cloud Gate was pretty neat.  Kids are drawn to that thing like you wouldn’t believe.  From there, I moved to the Great Lawn to observe the awesome Jay Pritzker Pavilion.  Talk about stunning!  It was a gorgeous blend of modern art and cutting-edge technology.  I was informed by a native that the acoustics were incredible.  I then meandered over to the Crown Fountain.  It was fun just to see what a blast the hundred or kids were having there.  Huge faces spitting out large volumes of water is the main drawn there.  Initially, I thought the faces were extremely cool, but after a while it just became kind of creepy.  But what I enjoyed most about Millennium Park was probably the least publicized area — the secluded Lurie Garden.  It was just a serene experience being able to kick off your flip flops, soak your feet in the cool stream and just relax. 

Favorite Millennium Park Hotspots:  Jay Pritzker Pavilion and the Great Lawn, Cloud Gate (AKA – The Bean), Crown Fountain and Lurie Garden. 

After my five-plus-hour jaunt, I decided to head back to home-base.  Manish was still immersed in his work, so I took a much needed power nap.  Shortly afterwards, I was awoken by a text message from my old friend Christine (my other Chicago friend), who wanted to get together for drinks.  Sounds good to me, and I knew Manish was game.  So after a quick workout at the gym, we made our way to her place at the John Hancock Tower.

We had to kill a little time, so we grabbed some snacks from a little Tai food stand to hold us over until Christine arrived.  She was as lovely as I remembered her and had a vibrant glow about her that only a 14 week pregnancy could afford.  How about some non-alcoholic drinks at the Signature Lounge? Christine suggested.  Let’s do it! Manish and I replied.  So off we went to the main elevator bank to begin our journey to the 96th floor.  What a great time.  The environment was very chill and, surprisingly, not crowded at all.  I highly recommend everyone catch a glimpse of the breathtaking Chicago skyline at night.  Perfect call, Christine!  Drinks and banter ensued, which made for a great evening all around. 

Saturday
I slept in until around 9:30 then hit the gym to start my day off right.  Afterwards, I suggested the Silver Palm Restaurant for brunch.  Travel show host, Anthony Bourdain, had recently declared one of their signature dishes called The Three Little Pigs as the “Greatest Sandwich in America”.  Oh man, did it look good!  I was hungry.  It didn’t take much to convince Manish, so off we went.  My voracious hunger was only trumped by my overwhelming excitement to consume this so-called “Greatest Sandwich in America”.  But sadly, the excitement was only short-lived.  My poor project management skills overlooked the painful fact that the restaurant would not open until 6pm.  D’oh!  I was crushed.  But I was still hungry so I would have to put my gluttonous adventure on hold and quickly find a new location for sustenance.  Manish took the lead this time by taking me to a swanky Irish pub called D4.  Sounds oxymoronic right?  It’s the best way I could describe it.  I mean, have you ever had a Black Mimosa before?  I have.  It’s a drink made up of Guinness and white wine served up in a fancy glass.  A true Irishmen would find this concoction an ungodly desecration of their national beverage.  Blasphemy, I tell you!  The meal was great, the conversation enjoyable as usual.  Now that my blood sugar level was returned to normal, I was ready to do some sight-seeing.

We walked over to the famous Navy Pier to be greeted by a carnival-like atmosphere.  A gentle breeze off Lake Michigan coupled with some brilliant sunshine made for nearly perfect weather.  I made a beeline to the architectural boat tours, as I had heard the 1 hr excursion was really worth the investment.  It really was, only reaffirming my initial thoughts on the city’s artistic flow.  We then grabbed a seat at the end of the pier to enjoy some refreshing marguerites and observe the menagerie of boats flow by.  Good times.  Manish’s close friend, Sonal, was in the area, so he and his lovely wife stopped by and chatted for a while.  Awesome people!  We would actually be meeting up with them for dinner later that evening, so we cut our conversation short to explore the adjacent man-made beaches.  Runners, bikers and swimmers lined the boardwalk.  It was just a cool place, the kind of place I could see myself spending a day just hanging out if I were a local. 

Later on that night, we met up with a group of Manish’s friends for dinner at Vong’s Thai Kitchen.  Our group was comprised of Sonal and his wife Surbhi, Jamila and her friend Milena.  What a great crew!  And the food was fantastic!  After dinner, we all decided to go out for some drinks. 

Manish suggested the low-key Rockit Bar, which everyone seemed fine with.  Our drinking plans were almost derailed after Sonal’s wife had forgotten her ID.  We were initially denied entry but after a private word with the bouncer, he offered up a solution:  “I accept a $20 no ID fee for entry”.  Unethical?  Absolutely.  Worth it?  It sure was.  Sonal surreptitiously slipped our new friend a twenty and on we went to enjoy our libations.  We showed up at the perfect time to land some prime real estate; a corner booth just beside a large window.  Score!  80s rock n’ roll music, drinks and laughs capped off a great evening. 

Sunday
Rise and shine!  We dragged ass out of bed around 7:00 am, picked up Christine around 7:45, and on the tennis courts by 8.  The pace of our session was pretty moderate.  However, the direct sun light quickly sucked the life out of me.  We volleyed for about an hour, which instantly brought back memories of just how bad I was and still currently am at tennis.  True to form, Christine thumped both of our asses pretty easily.  Just the same, it was a lot of fun.   

We also had Cricket on the docket, scheduled to take place immediately after tennis.  Unfortunately, the opportunity went bust when most of Manish’s crew couldn’t make it.  Oh well, next time.  I really want a shot at swinging that odd-looking bat.  Christine and I walked back together while chit-chatting every step of the way.  It was really nice.  I’m very happy we were able to reconnect after all these years. 

Back at the bat cave, I decided to pack up my things in preparation for my flight back home.  But before my departure, I had one more thing I had to do.  I had to try some famous Chicago-style stuffed pizza from Giordano’s.  Manish and I patiently waited about 40 minutes to get in around lunchtime.  It was well worth the wait.  The stuffed pizza was incredibly filling, but oh so tasty!

I can now officially say that I love Chicago!  In fact, I much prefer it to New York City.  I really mean that.  And of course, none of this would be possible without the generosity and friendship of my boy Manish.  He’s just a classy guy with a great heart.  Until the next time my friend…Next stop, India??? 

Below is a slideshow of all the photos taken that weekend: