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I admit: when I first set foot in Chicago over a decade ago, I was not impressed. Even when I moved there for college, I was pretty miserable in this Second City, wondering how I ended up going to school in a land where people walked slower, talked slower, and just plain didn’t seem as intense and cutthroat as New York, my then-favorite city.

Before long, though, I found myself falling head over heals in love with Chicago’s lakefront running path, the warmth of the people, the many cozy teahouses and coffeeshops to hang out and study in, the frequency of fun festivals downtown, the sheer beauty of the city’s architecture, the disparate personalities of each of Chicago’s many neighborhoods, the way the blue of the sky fades straight into the blue of Lake Michigan leaving no horizon line behind…Okay, pulling myself out of nostalgia and reminiscence-land…Suffice it to say that I never intended to leave after graduation and would still move back in a heartbeat.

I get a short reprieve this weekend as I head back for a friend’s wedding, and I can’t wait to soak in as much of the city as possible. While the following recommendations are perfect and centrally located for the first-time visiter, I will certainly be revisiting many of them in the two days or so that I’ll be back in Chicagoland.

Let’s begin our journey where Michigan Avenue meets the Chicago River, a location that divides the glitz and glam of the Magnificent Mile to the north and the arts and culture  to the south. Standing here, just look upwards and take in the majesty and beauty of the buildings around you. On the northwest corner, you will find the historic Wrigley Building, whose floodlights frame it in the night sky. The Tribune Tower sits across the street, its facade embedded with dozens of stones from historic places around the world. Looking up at the skyline, you also recognize 35 East Wacker (southwest of you), whose dome was featured in Batman Returns. Several architectural boat tours take off from here as well, including Wendella Boat Tours and one offered by the Chicago Architecture Foundation.

When you’re ready to move on, head north up Michigan Avenue, turn right just past the Tribune Tower, cut across what will look like a good place for office workers to take a lunch or cigarette break, around the traffic circle, and down those stairs you see on your left. I know, I know, not the most intuitive route, but arguably the easiest way to get from the “upper” level to the “lower” level of the city. (It’s linked above, but you can also click here to see a GoogleMap and directions for this route.)

Once you’ve navigated this path, you’ll find yourself at the famous Navy Pier. Okay, I admit this is a bit of a “tourist trap,” home to the the carnival-style attractions, a Fun House, and an IMAX theater, but it is also home to the Chicago Children’s Museum, Chicago Shakespeare Theater, and panoramic views of Lake Michigan. It’s one of those iconic places that, well, you can’t visit Chicago without seeing at least once.

As you leave, cut north across Jane Addams Memorial Park on your right, just outside the entrance of Navy Pier. On the other side, you’ll arrive at Ohio Street Beach. Now this certainly isn’t the best beach in the area (you’ll find a bit further north), and you certainly can’t compare this tiny little strip of sand to, say, Hawaii, but hey, who knew there’d even be any actual beaches in the midwest?! I would come here every once in a while when I just needed to “get away” from the city without actually leaving it. Both the beach and park are pleasant places to idle away a few hours; at the very least, they create a more scenic return to the Mag Mile. Just duck through the underpass when you’re ready to head back west (along Ohio St) to Michigan Ave.

While the “Magnificent Mile” technically began at the start of this itinerary, the southernmost blocks house mostly chain stores (including Starbucks and Walgreens) that you could find pretty much anywhere in America. The closer you get towards the Water Tower, the nicer the stores get and the heftier the price tags. Burberry, Cartier, Gucci, and the like can all be found within blocks thereof.

“Water Tower” actually refers to two different places: an eight-story shopping complex, and a historic landmark across the street that commemorates the Great Chicago Fire of 1871. Legend has it that the blaze that burned down nearly a third of the city began when Mrs. O’Leary’s cow kicked over a lantern in the barn. That tale has long since been disproved, but it continues to live on in local lore. And while the fire left tens of thousands of people homeless, it did kickstart the reconstruction process that made Michigan Avenue and downtown Chicago the glitzy tourist attraction it is today.

Finally, as you meander the streets of the Gold Coast just north and west of the Water Tower Place, you’ll encounter high end shops like MAC Cosmetics, Hermès, and Prada. Spiaggia, one of Obama’s favorite restaurants and holder of a Michelin star, is also in the neighborhood, as are other great restaurants like Gibson’s steakhouse and its sister Hugo’s Frog House and Fish Bar. (I was a bit disappointed by their signature frog legs — they really do taste like chicken — but love everything else I’ve tried there =))

Finish your day off — or just take a shopping break — relaxing at nearby Mariana Park, a cute, triangular little plaza surrounded by ritzy cafes and restaurants, or Washington Square Park, a peaceful public space a few blocks further west.

To be continued in Chicago for First Timers – Part 2

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