Chicago Baby! – My Crazy Travels

I’m Back! It’s a bittersweet feeling back after being away for so long. I love the adventure and novelty of being overseas , yet I’m always attached to the things I hold dear. At the end of the day, I still care about Singapore dearly.

From Mid- December to End December,  I visited the United States for various reasons – mainly to visit Northwestern University and have a good post-ORD holiday. It’s also very likely the last family holiday my family has in a while because my brother is starting his A Levels next year and I’ll be matriculating in September.

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One of the  biggest things I was looking forward to was finally seeing snow  – I was going in the winter and the weather forecasts were promising chilly winds in Chicago. I don’t know what was wrong with me but I was actually excited for this. Worst Thing to Look Forward to but more about that later.

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When snow first started dropping, my heart jumped out. We were going to be spending Christmas in New York later and I was really looking forward to a White Christmas (it didn’t play out …) . Snow is  cool, because it’s so delicate and just flutters around. It’s not like rain which just punches through your skin, snow is actually beautiful. You can also observe really interesting designs on snowflakes. But with great wonder comes its fair share of difficulties. 40% of our luggage to the US was actually Winter Clothes. My family adopted the philosophy that since we have never been to a winter climate as a family before we better overprepare rather than underprepare. Ya, we had like 10 luggages guys.

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That’s me rocking the winter gear. Nothing much there.2013-12-16 20.39.27

One reason why I was really looking forward to coming to Chicago is the fact that this was a monumental city. Famous people did amazing things here – and the first skyscraper was built in Chicago as well. I’m an architecture fanboy when it comes to beautiful buildings. I find it delightful how people craft things out of thin air – and I imagine the tireless effort it took to construct such things. Chicago is also where a lot of famous actors like David Schwimmer made their break.When I was in Italian Village, a really good authentic Italian restaurant, I saw them showing off all  the famous people that had come there, including James Gandolfini, Rahm Emmanuel and Jerry Seinfeld. Wow right?

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The cityscape was just breath-taking to wake up  to each morning. It was almost like you’re an ant, crawling amongst giant buildings.

Ok now onto the important stuff : Food. Everyone  has asked me what’s the must-eats in Chicago. First thing first : The Chicago Dog. Now American hot-dogs are nothing crazy by themselves – it’s like our version of the curry puff, a cheap accessible snack.  What’s really good about the Chicago dog is the variety of flavours on it : there’s a dill pickle, a tomato, relish, mustard, ketchup and my favourite : a pepper. It’s easy to find it in any public location .  I didn’t really enjoy it too much – it was an interesting concoction but beyond that I missed a good regular hotdog with good relish.

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Of course, when you think of America, you think of burgers as well. I didn’t try many burgers while in the US (which I regret , but there was really too much to try) but I did try the burgers from Five Guys which is a chain here. They really grill their burgers well and the meat is fresh. Oh man, I loved this burger. Been craving a good burger since.

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What’s Chicago without the deep-dish pizza eh?  The pizza is basically a pie where the bottom is a huge layer of dough and cheese. I personally liked the BBQ Chicken Pizza , but my family said the Meatball was better. I’m weird. We ate ours at Giordano’s which is apparently the best pies, but there are reputably better ones with better crusts / flavours. I’ll be studying here for the next four years so I’ll give my review then 😛

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Now when I hit Chicago, there was one place I wanted to go the most. Harry Caray’s Steakhouse. It’s reputably the best steakhouse in town.  I had a 12oz Dry Aged Steak – which was pure heaven. The steakhouse is a real chill place with all sorts of memorabilia. There’s also Morton’s in the US for those who want to try those , but I was insistent on the local favourite.

We visited the Sears towers (now the Willis Towers) to check  out the view . I wasn’t disappointed. The Willis Towers was the tallest building in the World for some time, especially since it was intentional to show the prowess of Chicago after the great Chicago fire which wiped off the whole downtown of the city. Now if that’s not a comeback story to inspire you,  I don’t know what is. Hearing the determination of the people behind the tower, I felt compelled to dig in deep when I felt exhausted by my own worries. There’s big things waiting.

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Of course, I took a trip to the main reason behind the whole trip. We went uptown to Evanston where the winds are colder and the houses are beautiful to visit Northwestern University. I could say a lot about my college – but I’ll only say this. I can’t wait to go in. REALLY!

There are plenty of cool things to visit in Chicago itself . I loved the Bean which is the ultimate selfie prop. It’s a huge reflective art-piece where you can see yourself and everything around you. I like how you feel like you’re staring into an abyss at certain angles. A friend of mine challenged me to try taking a picture without anyone else inside  – that’s pretty hard. You guys should try it yourselves.

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The Field Museum is a must visit. I actually enjoyed this museum – it was grand, and had artifacts that were actually interesting. SUE is the star of the show though – most of the bones in the skeleton are from actual excavation. It’s very grand and reminds you that you’re very small.

My dad got super excited to visit Moody Bible Institute as well – started by DL Moody , one of the biggest Christian Educators in the world who has inspired so many people to take up the cross and grow deep in the word. Inspiring people make big differences in turning points of our lives.

The Art Institute of Chicago was swanky as well – it was HUGE, I gave up after 20%. But the artifacts and paintings that I did see – oh wow. Below is one of the exhibits in the room of miniatures where the artist organised the construction of finely detailed miniatures. My trip to the US surprisingly grew my appreciation of the finer things like art, theatre and music.

The Navy Pier is a to-go in the summer. Unfortunately in the Winter, it was closed and looked pretty dreary. Damnit.

In addition to shopping, eating and visiting the sights – Chicago is simply a beautiful place to visit. The Winter is killer but truly a sight. I met Laura in NY and she showed me some of the same pictures I took but in Summer and it’s a whole nother set of sights on its own. I”m looking forward to coming here soon – will be posting my travelogues on NY and Vietnam soon!

Till then,



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