Anyone that has visited both Chicago and New York City for reasons other than business knows that the term “Second City” is a nickname that is very apropos. New York is undeniably one the the world’s urban marvels. But if you have been to Chicago, like REALLY been to Chicago, then you might often wonder why anyone would dare relegate this wonderful city to second place status. There are more restaurants, bars, museums, jazz clubs and top notch lodging establishments than you can shake Mrs.O’Leary’s cow at. This town has an energy that it and only it possesses!

The beauty of it for us is that we can check in at The W Chicago – Lakeshore, and while still in our travel jeans head downstairs and stop into Current, the hotel bar/restaurant. (No. This is not a paid endorsement. We just LOVED it! So we mentioned it!) We sip (One man’s sip is another man’s shot. Remember that at any bar in this city) on a couple of Old Fashioneds and then we step out of the door and instantly become immersed in that aforementioned “energy”.

Now “winging it” spontaneously is definitely an option in Chicago as there is just so much to do but we suggest that you have at least something close to an itinerary if you want to catch the finer things that The Windy City has to offer. A rigid itinerary will absolutely fall apart. This much is certain. We have been to Chicago only 1 or 2 HUNDRED times so trust us when we say that on your way to a certain place, you will find that you have stopped in at least one unscheduled bar or shop along the way. But there are definitely things that you do not want to miss so keep it loose but keep it tight. (If you were not confused by that reference then you are going to do jussssst fine here!) 

The first thing that you (and all humans) must do is eat. This is also a required first step if you are especially “thirsty” after dinner like we seem to always be when on a trip. You can hit the touristy spots that are famous like Navy Pier for a Chicago style sausage….IF you are 23 years old. (And if you are 23? We have likely missed our mark with this entire “upscale” venture of ours.) Instead, we suggest that you try a place like The Signature Room at the 95th that has tablecloths, great views of the downtown skyline as well as scrumptious seafood dishes. If you desire a more land-based experience with your feet closer to the ground and a meal that never once relied on gills to survive, then Gibson’s Steak House will certainly be worth the trip. Girl and the Goat probably has downtown Chicago’s most eclectic menu where award-winning chef Stephanie Izard serves up original small plates from a dramatic open kitchen.

*At this moment we will give you the chance to click over to your Kendrick Lamar station and we will wish you the best if you don’t like jazz because we are about to give you a heavy dose of it. We will wait….*

Yay! You are still here! That must mean that you are ready for the jazziest and classiest juke joints in town. Chicago is the home of jazz in the midwest. Legends like Jelly Roll Morton and Papa Joe Oliver brought the swinging style of improvisational “Dixieland” music from New Orleans in the early 1900’s and it quickly took off in the north and became the musical standard in Chicago. Remnants of this golden era are easily observed at The Green Mill where Al Capone and other gangsters used to hang out in the 1920s. These days, however, it’s all about the music. Owner Dave Jemilo, who returned the club to its original luster in the 1980’s, books jazz performers with a discriminating ear. Local favorites Frank Catalano and Patricia Barber both maintain residencies throughout the year and the music often goes as late as 2am (5am on Saturdays). Arrive early, grab a cocktail and settle in for a long evening.

If you thought there was only one establishment that was historically steeped in the jazz culture then…..Well…..You knew better and we appreciate your sense of humor. Andy’s Jazz Club is another downtown haunt where you will find anything from a sultry soloist accompanied by a grand piano to an eight-piece ensemble. Andy’s kind of cheats in this article because it crosses the line between a fine dining establishment and a swinging auditory house of delight.

As you well know, one of the most glorious aspects of the jazz music genre is that you can find a favorite performer that is local, never leaves your town and is always around to make you feel like snapping and applauding. The other side of this is that there are also world famous jazz musicians that have absolutely earned their fame and you relish the rare opportunity to hear them perform the favorite song from your Spotify playlist. Jazz Showcase will definitely fulfill your desire for the latter.  Jazz Showcase continues to bring in local, national, and international talent. Over the years, they have had such legends as Count Basie, Herbie Hancock, Art Blakey and Dizzy Gillespie. They even have their famous 4 pm Sunday Matinee that is geared towards families should you be traveling with your favorite munchkins and want to expose them to “real” music (Free admission for kids 12 and under).

There are many things to enjoy and explore in Chicago. Museums, festivals, a world class aquarium and historical tours that include everything from its intriguing bootlegging tradition starring one Alphonse Capone to how a very nice cow managed to burn down a whole perfectly good city. But we have chosen to only highlight “The Chi” which consists of the finest restaurants that are bereft of flip flops and the most delightful music reserved for the most discerning ears.

New York City is a thing unto itself and will certainly grace the pages of this website sometime in the very near future. While Chicago is certainly not a mystery to anyone it is quite the conundrum to us how anybody who has visited The Chi would ever conceive of calling it “Second” to anything.

If you disagree then we would please ask that you read this article for a “second” time and book your trip. If you even remotely follow any our suggestions and come back disappointed? It would be a first.