Back in 2001 my friend Juan and I, on a whim, decided to treat ourselves to a guys weekend in Chicago. We had so much fun the first trip turned into one more and then another and, after the third year it became a ritual. Throughout the years many things in our individual lives changed, jobs, a divorce then a new marriage a few years later for me. For Juan, an adopted child, congestive heart failure, and a battle with cancer but the Chicago trip was the one constant throughout all of this change.

The Chicago trip was the reward that we allowed ourselves for a year of incredibly hard work. Juan is an artist and I'm a writer and we were both busy building our careers and saving for this trip was always a significant sacrifice. Fast forward a decade and we've stayed true to our commitment to this pilgrimage for the last twelve summers.

At first we had a very limited budget and ate far more Subway sandwiches than a person should. Our first year we each had a budget of $160 in spending money for three days and we somehow managed to do it. We must have put twenty miles on our shoes each of those three days.

For the first six years we stayed at was an ancient Hotel that was literally a throwback from the 1920's called The Cass Hotel. We often referred to it as The Ragitty @ss. The rooms at the Cass were reasonably priced and relatively clean but there was still a certain seediness about the place. Around 2010 it was snapped up by a international hotel chain, renovated, and the personality was polished right out of it.

A few years later we began staying at the Seneca Hotel and until it eventually suffered the same fate as the Cass. Our first few years we were all about the nightlife and there was plenty of it to be had. We have so many unbelievable stories, so many experiences during these trips, outrageous things that a person just couldn't make up. I know now that these memories are worth ten times whatever was spent on the trips. One day I promise I'll write a book about it.

The mid-nineties brought about a ten year revival of Jazz and big band music and it was popular with the younger crowd. I remember Jilly's on Rush Street, hopping the redline train to the Lawrence station, dressed in my finest suit to listen to big band at the Green Mill. The Alan Gresik Swing Shift Orchestra packed the place. There was so much class, so much energy there, it was incredibly fun.

As the years progressed so did our interests. Each year the Chicago trip became a little more about food, music and culture than about partying. After spending so much time in the city we learned to navigate like a local and since the advent of the smartphone we would easy pack three times as much out of the trip.

We got to know the soul of the city. Every year we felt more comfortable venturing further and further out. We visited Ravinia to enjoy a concert on the cool green grass, Oak Park to experience Frank Lloyd Wright's many architectural masterpieces. We caught a cab to Bucktown for a decedent vegetarian feast at the Green Zebra restaurant.

This year we came to the conclusion that this would be will be the final trip to the Windy City. These words had been uttered by us before in prior years but I don't think we meant it quite yet. Although this was our most enjoyable Chicago trip ever we both decided that we had seen the city inside out, backwards and forwards, and definitely for better and for worse. We were a little melancholy but we knew that this was it and we said our goodbyes to this wonderful city in style.

One of the many highlights this year was Rick Bayless' restaurant Xoco. I ordered the vegetable coldas, it was a stew of veggies, wild mushrooms and potato/masa dumplings. Juan had the spare rib and red chili coldas. As good as the food was, we both agreed the best part of the meal by far was the hot cocoa. The staff at Xoco roast and grind the single-sourced cocoa beans right there at the restaurant and words cannot describe how delicious or different this is from any hot cocoa you have ever tasted. Believe me, it is mind-blowing...a melted truffle in a cup.

Another highlight was seeing Sara Marie Young at Andy's Jazz Showcase. Look her up, she will one day soon be a household name.

We stayed at the Millennium Knickerbocker Hotel and it was in the best location ever. Most everything was close by, the rooms were modern and clean and the concierge gave great suggestions. The Knickerbocker even has a little bar downstairs in the lobby with a jazz trio playing most nights. It was nice to relax down there either before or after the night on the town.

The people of Chicago are, hands down, just some of the best souls I've met anywhere. They are friendly, diverse, open-minded and just plain cool. Back in 2002, which I think was our second year, an employee of a shoe store on Michigan Avenue clued us into the nightlife on Rush Street. Back then, it was lined with jazz clubs and nightspots that were open until 4:30 in the morning. The Rush Street of today is just a shadow of its former self.

This year we were shocked to learn that two of our regular spots left standing, Jilly's and the Hunt Club were demolished. These clubs were reduced to vacant lots, gaping holes in the cityscape where only the ghosts of happy memories remained. We were just in Jilly's last summer listening to an amazing band and having the time of our lives. Rumor has it they're putting up high end retail chain stores in their place.

Little by little, I suppose just like our youth, the old Chicago is fading away and in its place has settled a little bit of wisdom. Chicago will always hold a special place in my heart but if growing older teaches a person anything, it teaches you how brief our time on this Earth really is. Life is too short to continually go back to the same familiar places. The Chicago of old will live forever in our smiles and laughs as we revisit our memories.

For our next trip, we'll choose a new destination. Will it be Montreal or possibly Vancouver? We're not sure but there's one thing that's certain, there's nothing more valuable than making new memories.