Enjoy Chicago like a local

I recently got back, feeling greaaaat, from the trip of a lifetime. I spent three amazing weeks in the East Coast, exploring four major cities of the USA. My trip started in New York, where my bestie from high school lives, moved on to Boston and Washington, DC, and ended in Chicago, where I camped at a hostel for five nights, and was lucky enough to catch up with some of my awesome family.

My first time in the West was much more educational and fun than I had anticipated. It was extremely pleasant, weather and otherwise. News from there is that a change is coming. Most of my preconceived notions came flying back to homeland. I observed, more than once, how our generation of Americans believes in marriage, more than one child, and healthy food. It is the perfect cross-culture experience I wish for everyone.

In my first post in this four-part series, I’ve made a list of must-dos in Chicago, if you’re visiting for less than a week. A city not to be underestimated, there is A LOT to do here. As a lover of the arts, culture, music and lying in the grass, here are my most cherished memories of the Windy City.

Eeeeeeee!

Walk the Magnificent Mile

It’s the safest way to start exploring the city. Michigan Avenue, popularly known as the Magnificent Mile, is a kilometre and a half of awesome. Famous for being home to every luxury brand you know, besides those you don’t, some very beautiful and important buildings can be spotted here.

Since my hostel was right in the middle of the Loop (Downtown Chicago), I did my fair share of walking up and down this street. Grant Park, which comprises The Art Institute of Chicago, with its resident green bronze ‘guard’ lions in the front, Buckingham Fountain, that refused to fit in a frame when I was too close, and Millennium Park, home to the glamorous Chicago bean, is lush green and, on most days, sparkled after a short spell of rain.

Beanie!

I’d then walk towards Oak Street Beach, at the end of the mile. Basking in the sun but on my guard against the rain, I’d stop at a bridge that runs parallel to the Renaissance-inspired white terra cotta-tiled Wrigley Building, the chewing gum giant’s headquarters, for a sigh-worthy view of the city. Opposite it is the Chicago Water Tower, originally built to pump the very green water out of Lake Michigan that flows below it, but now a tourist office.

One day, before I found a bench at the beach, I caught a quick shot of the John Hancock Center, once the tallest building in the world, in all its black metal glory—antennas and all. I should add, somewhere in between all of this, many of the shopping places, and Ghirardelli’s chocolate and ice cream store, were very welcome distractions.

Awesome in the name.

Visit the Fine Arts Building and the Art Institute

It was so cute to see how excited volunteers at my hostel were about the lift in the Fine Arts Building, a block from my lodging. Why? “Because it’s operated by a live human!” Small joys. Apart from riding in this historic building’s vintage elevator, walking its corridors and down the art and music school’s antique flight of stairs—appreciating the beautiful paintings that adorn the walls—is quite an experience. My favourite part was tip-tapping to the music that streamed out the closed doors on every floor. There’s nothing like visiting a music school during practice hours.

According to my Lonely Planet-wielding Swiss roommate, the Art Institute of Chicago, right opposite the Fine Arts Building, “should not take you more than two hours to cover”. I was there for a little less than five. I see myself as someone who believes in Santa Claus more than visiting a museum, but I’d kick myself if I hadn’t done this. For anyone who remotely appreciates colours on a canvas, and the history of art and culture, this place is a must-visit. For me, the modern and expressionist art wing was a total win. The Indian arts’ section and the one with various American Indian wears was a delight too.

Somewhere in the middle of the Fine Arts Building, and funky tribal wedding wear at the Arts Institute.

Stand on the ledge at Willis Tower’s Skydeck

Not recommended for the faint hearted, this was definitely the moment of my trip to this city. The observation deck on the 103^rd floor at Willis Tower, formerly known as Sears Tower, offers a breathtaking view of the city as well as four states—Wisconsin, Michigan, Illinois and Indiana—on a cloudless day. It is installed with four ledges that extend four feet outside the building, made of clear glass on three sides, which made me feel like I was suspended in mid-air!

From on top of the world!

Lie on the grass in Millennium Park

I spent half a beautiful summer’s evening doing this. The park is home to a massive theatre screen, so in between my short naps in the green, I caught bits of Amadeus and a light drizzle.

Movie time in the grass.

Take a bus to Hyde Park

My hostel’s notice board was full of recommendations by locals on things to do. Early one morning, I ambled to the board and randomly picked this one, a 20-minute bus ride to the south of the city. The bus dropped me at one of the numerous lush green parks in the middle of the area, from where I walked to the University of Chicago—past rows of little brown-bricked houses with neatly trimmed lawns.

Though it predominantly houses students and facility, Hyde Park is a fairly diverse neighbourhood. I walked past several churches, quaint bookstores, Frank Lloyd Wright’s landmark architectural project—The Robbie House—and Obama’s home. I spent most of my afternoon exploring the Oriental Institute and the Smart Museum of Art in this area, which are a hotchpotch of art and culture, and have free entry. 

Go thrift shopping at The Brown Elephant and see the Wrigley Field

The Brown Elephant, a thrift store by the Howard Brown Health Center (Midwest's largest LGBT health org), is a retail store with a cause. Proceeds from it go towards services for more than 50% patients at the Center who are under or uninsured. A short subway ride north of The Loop, I got to the store an hour before it closed. It’s basically a really large warehouse; where I not only sifted through racks of clothes, bags and shoes but also was tempted to buy crockery, jewellery and furniture! I ended up picking up a few books and comics minutes before the attendants were ready to go home.  

On my way back, hordes of baseball fans, sporting White Sox jerseys and caps, streamed out of the metro station. My curiosity got the better of me, and I mapped my way to the ginormous Wrigley Field, where this major league club was playing. The field has netted doors, manned by three people at the time, which allowed me a sneak peek inside—the baseballers looked right out of the movies. Their ardent fans’ zealous and loud encouragements followed me all the way back to the station.

Eat

Chicago’s famous deep dish pizza cannot be missed! I sampled this heaven-on-a-plate at Lou Malnati’s Pizzeria and was absolutely bowled over. The tug of war between the cheese on my plate and that in my mouth was the best fight I’ve witnessed.

I always wanted to chow down a true American-omelette breakfast. Yolk, at the southern tip of Michigan Avenue, made my wish come true. I did not want their five-egg omelette, stuffed with possibly every delicious thing in the world, to end. It’s even more of a delight with their thick strawberry and orange juice.

As luck would have it, I was right in time for the world’s biggest and Chicago’s 33-year-old food fest, Taste of Chicago. A stone’s throw away from my hostel, I bought strips of coupons at the venue, and was off to sample as much as I could from the 30-40 odd stalls, put up by the best of the best restaurants of Chicago at Grant Park.

Was that afternoon a daze; from what my taste buds remember, the Bobak Sausage Co's Polish sausage with grilled onions and mustard, chicken pot stickers (dumplings) at Star of Siam, and Original Rainbow Cone’s multi-coloured ice cream are what my dreams are made of.

Food trail—epic burger and shake at Epic Burger, Yolk’s classic five-egg omelette, and Ghirardelli’s ice cream. Y-u-m.

Visit Green Mill for a live jazz performance

My hostel organised an evening out, on my last night in the city, to one of Chicago’s most cherished and famous jazz lounges, Green Mill. It was the best farewell I could have asked for.

I read about this iconic place while planning my trip, but honestly, I was a little scandalised. It is famous for once being owned by the notorious gangster, Al Capone, where he loved to unwind with live jazz performances. Our group of five along with Chuck, the guide, entered this shady-looking Chicago hotspot at 8pm, sharp, for seats right in front of the band. Chuck pointed out a semi-circular table, with its backrest to the stage, as Capone’s corner. He explained how the mafia lord would enjoy his music and watch the door to make sure he doesn’t leave with a bullet to his head.

What a yay!

We grooved to the captivating music of Matt Ulery’s Loom, as the epic club filled up. Though it felt like a local train before we called it a night, Chuck insisted it’s much crazier during the winters! Later, we walked a block to see the birthplace of Hollywood, the Essanay Theatre, where Charlie Chaplin made most of his silent movies. 

For best results, visit this neurotic-weather city in summer.