Back in 2001 my good friend Juan and I, on a whim, decided to have 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, an adopted child and a battle with cancer for Juan 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. My friend Juan is an artist and I’m a writer and we were both very busy building our careers and saving for this trip was always a huge 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 four days and we somehow managed to do it. We must have put 30 miles on our shoes each of those four days. The hotel we stayed at was an old throwback from the 1920’s called The Cass Hotel before it was snapped up by a hotel chain a few years ago and renovated. The rooms at the Cass were reasonably priced and relatively clean but there was still a certain seediness about the place. 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 that have been created during these trips. Outrageous things that a person just couldn’t make up. 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 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. Every year we gained more confidence and felt comfortable venturing further and further out. We visited Ravinia to enjoy a concert on the lush green grass, Oak Park to experience Frank Lloyd Wright’s many architectural masterpieces. 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 year of our trip to the Windy City. These words had been uttered by us before 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 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.
This final year we stayed at the Millennium Knickerbocker Hotel and it was in the best location we ever had. 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, 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. Today, Rush Street 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 and only the ghosts of happy memories remained. We were just in Jilly’s last year listening to an amazing band and having the time of our lives. Rumor has it they’re putting up high end retail stores in their place.
Little by little, I suppose just like our youth, the old Chicago is slowly fading away. Chicago will always hold a special place in my heart but if growing older teaches you anything, it teaches you how short our time here really is. 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.