Chicago is like returning to an old lover after many long nights away. A hint of familiarity tinged with nostalgia and the inescapable feeling that it will never be as magical as it was once.

I first saw her from the airplane window. Patches of green bleeding in between the precise highways, the outlines of baseball diamonds, pools and cemeteries all coming into view. The city lay before me – arms outspread to welcome me home.

Maybe now is the right time to admit that this is my first time in Chicago. The city’s shimmering depth and quiet appeal had fascinated me for years but I never had a reason to go, until I made one.

Trying to gauge the personality of a city is a tricky business. It’s as futile as trying to compare memories with a friend – each person leaves the conversation convinced that their recollections are right and no one is the wiser. Of course, my interpretation of a place is colored by my perspective, hopes and dreams; and today, Chicago was just what I needed.

I started with breakfast, as all good days do. After an uneventful ride on the CTA’s Blue Line, I found myself downtown. The city was just waking up – early commuters were just beginning their days and neon signs flickered to life.

I made my way to an independent café because I believe one of the best ways to gauge a city is to see where its people drink their coffee. Café hopping is as much an exercise in human anthropology as a practical necessity – staying awake after a red eye flight requires more than just adrenaline.

I always do a minimal amount of research to map out a few key spots but leave most of my itinerary up to chance.

After realizing that the Chicago Diner wouldn’t open for another four hours, I made my way to Goddess and The Baker near Millennium Park. This clean yet quirky café had a modern feel with local touches. The pastry case presents a ravishing array of sky high cinnamon rolls, layered cakes, a rainbow of macaroons and cookies shaped like cartoon animals. Their menus spans from selective coffees to liquid dessert with just a hint of espresso and also includes a selection of teas plus beer, wine and sake in a refrigerated case. I settled on S’mores Frapp, a dreamy combination of espresso, chocolate, marshmallow crème and graham crackers topped with whipped cream and served in a mason jar, it was sweet enough to down without a second thought but provided enough caffeine to shake off the remains of jetlag…