An Ode to Chicago: I love San Francisco, but I’m in love with Chicago.

My brother George is getting married this weekend. After three months away, I am leaving San Francisco heading to back to Chicago for the first time since – the city that I love, the city that I had called home for over 20 years. I get an opportunity even Ferris Buehler would be jealous of.

People always ask me my thoughts about Chicago; and invariably how we compare to New York where I’ve been countless times. New York has an energy that cannot be matched anywhere else in the entire world. Chicago too has its feeling of bigness. It is truly a massive city, worthy of its status as one of the great cities of our country, if not the entire world. However, what always strikes me about Chicago is how friendly Chicagoans are and how accessible everything in the city is… I always proudly say, “Chicago is a small town but with a lot of people.” I also say, “Chicago is Gotham City and The Dark Knight watches over us all.” (I’ll never forget that feeling I felt when I walked back home from the IMAX at Navy Pier watching The Dark Knight for the seventh time at the theatres. I had the biggest smile as I thought to myself, “I live in Gotham City.”

My recommendations for things to do, in no particular order… All of this is stream of conscious as I sit aboard a bird bound for The Windy City, excitement building in my heart.

  • While Chicago is center to a great many sports teams, some arguably more successful than others and I believe most people would say it’s a Bears (and now the past few years, Blackhawks) town since they unify the city and football has been the de facto national pastime for years, a visit to the friendly confines of Wrigley Field is a must. This year, I was fortunate to hold season tickets, sitting along the third baseline in the upper deck with a perfect view of the play; and as long as I was there, we won. The most electric I’d ever seen the city was during the playoff run of 2003 when we were five outs from going to The World Series (a lump forms in my throat as I write this) – the Cubbies came thisclose to meeting the Yankees (who would break the Boston Red Sox faithfulls’ hearts – Aaron Boone is still a bad word in Beantown). Even the ’08 (was it that long ago? I cannot get google on the plane) season when they were the best team in baseball during the regular season, didn’t compare. The only other time where I felt the city was that jacked up were the two Blackhawks Stanley Cup title runs (the last one a couple months ago very special to me cos it bonded my two brothers and I, the only team we all agree upon rooting for together). There is no more an emotional moment before a game than Jim Cornelison singing our national anthem, literally a goose bumps full few minutes – every single time I’m at the game. Special acknowledgment should e given to the ’06 Bears NFC Championship, ’05 White Sox World Series title, and all the Bulls title runs during the Michael Jordan years.
  • Late afternoon or early evening, you have to have a drink on the terrace (16th floor) of Trump Tower. Enjoying a drink outside, you will be rewarded with the absolute most spectacular view of downtown Chicago. Equal parts romantic and breathtaking, to me it has replaced The Signature Room atop the John Hancock tower as the place to take in the city. If you have time for both, you will come out of the day and night significantly happier. (Also included in this bit should be the Sears Tower, for more breathtaking views this time from the tallest building in Chicago.)
  • Brunch is huge in Chicago. You’ll find families, couples, late night partygoers and the hungover all eating at their favourite spots. I love The Bongo Room on Milwaukee Ave in the eclectic Wicker Park neighborhood, as recent as 15 years ago (when I moved there), extremely dangerous (some – like me – would say “lively”) where its street corners a majority of prostitutes called home, easy availability of drugs, gangs, etc. Now, still with an abundance of character, it’s home to hipsters and many young families with strollers. After breakfast, walk around the area; if you’re up for day drinking, there are many bars that will satisfy your thirst.
  • Chicago is a great museum town. The Art Museum. Shedd Aquarium. The Museum of Natural Science & History. The Museum of Science and Industry (one of the only holdovers from The White City in 1892 when Chicago was at the center of the world hosting the World’s Fair where, among other things, Pabst won the blue ribbon for best beer and a sociopathic serial killer named H.H. Holmes brutally murdered scores of unsuspecting women moving to Chicago for a better life).
  • Chicago is famous for its architecture. Home to such famous architects Frank Lloyd Wright, Daniel Burnham, Charles Atwood, etc., I would highly recommend the architectural tour along the Chicago River. A great and relaxing way to take in the city.
  • Speaking of the Chicago River, everyone needs to watch the river turn green and visit Chicago during St Patricks Day weekend, our answer to New Orleans Mardi Gras. Portending the beginning of Spring, Chicagoans defiantly say goodbye to Winter, drinking all day and all night in T-shirts and jeans. Drinking here is serious business and should not be taken lightly. Amateurs are not welcome.
  • The holiday season in Chicago is magnificent. The night air is crisp (for some cold). The days hopefully filled with snow. And the stores up and down Michigan Avenue are teeming with holiday shoppers. It’s a scene of an old 1940s black & white movie. If Marshall Fields was still around and if you happen to visit during the holiday season, having a look inside their large windows will reflect back the kid in you. Afterwards, take a walk around the theatre district and catch a show. Have dinner at Petterino’s, where their stuffed pepper is ah-maze-zing.
  • Chicago neighborhoods are plentiful, all with a character and cadence its own. You should spend time in each, giving it at least a morning, afternoon and/or evening. I recommend the West Loop (where I currently own my condo and have some of the best restaurants in the city – The Girl & The Goat, Nellcotte, RM Champagne Salon, Maude’s Liquor, etc.), Old Town (home to The Old Town Art Fair), Wicker Park (my favourite part of town) & Bucktown, the Gold Coast, Lincoln Park, Lakeview, Wrigleyville, etc. all for different reasons.
  • When discussing neighborhoods, the city comes alive during the summertime, as the population of people outside seems to double (if not more). Every weekend, a neighborhood will host an outdoor festival. Streets are blocked off. Bands play. Restaurants have booths with their finest available to eat. And beer flows aplenty. The entire city joins in the fun, from those just born to those enjoying their golden years. There are cities where its people enjoy the outdoors but no city embraces an outdoor event like Chicago. Some of my favourites include The Old Town Art Fair, Old St Pat’s Block Party, Sheffield Garden Walk, Wicker Park Fest, Taste of Randolph, Division Fest, Lincoln Square Wine Stroll, Taste of Lincoln, etc.
  • Along Lake MichiganChicago is known for its restaurants. Whether you prefer fine dining or just a hole in the wall, this city has it all. Chicago steakhouses are unparalleled. Even the “chains” are better here than anywhere else. My favourite is Mastro’s (where if you go, order the seafood tower, the bone-in ribeye fillet, and the butter cake for dessert) – you will not be disappointed and you will come back.
  • The music scene in Chicago is unparalleled, no matter what kind of music you like (as long as you like live kind). While we have smaller venues like The Elbo Room, Subterranean, Schubas, the Double Door (where the Rolling Stones once kicked off their North American tour in a surprise visit), Martyrs and so many more, we are famous for our events at Wrigley Field (including Pearl Jam, Roger Waters, The Police, Jimmy Buffet, etc.) and the three-day mega-event Lollapalooza (large acts like Radiohead, Wilco, Rage Against the Machine, NIN, Foo Fighters, Eminem, etc. and smaller ones like MGMT, Passion Pit, Girltalk, etc.) Of course, what we are famous for is the blues. Kingston Mines. Legends. I remember like it was yesterday though it was 15 years ago, Pistol Pete scorching his guitars at B.L.U.E.S. on Halsted, giving us renditions of Jimi Hendrix, Muddy Waters, BB King, etc. All that being said, I could have written this section with two words: Buddy Guy.
  • The Chicago bar scene is great. It’s better than great. I will leave it at that. Saturday drinking during college football season will always have a special place in my heart. And rallying to keep the festivities going thru the night is the stuff champions are made of.
  • More than anything, it’s the people of Chicago that leave an indelible mark upon you. With both a healthy mix of transients visiting and those that grew up here, I’ve met my best friends (outside high school) in Chicago. And now some of them have left, traveling far and wide – including me. But many of them remain. And, whether in or out of Chicago, they all still remain just as big a part of my heart, if not moreso, as the days I first met each and every one of them.

So there you have it. Surely I’ve omitted quite a bit? What would you do if you had a couple days in Chicago?

I love San Francisco and the Bay Area, but I’m in love with Chicago.

As a friend of mine once so astutely put it “Cecil: you’re in love with Chicago, but you’re having an affair with San Francisco…”

PostScript: I eventually fell in love with San Francisco too, but Chicago captured my heart first, and it will hold it last. Recently, after four years in the Bay, living in beautiful Sausalito, I moved back to Chicago, ready and living my next series of adventures.

The View from The Trump Tower, 16th Floor






4 thoughts on “An Ode to Chicago: I love San Francisco, but I’m in love with Chicago.

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