Our Whirlwind Trip to the Windy City


Alternative title to this post: How to Spend 1 ½ days in Chicago

I suppose I should begin with our main reason for going to the Windy City in September 2017: Hamilton. Yes, my friends, the best future husband ever gifted me with the golden ticket last Christmas. While I found it hard to wait nearly a year for the show, it must’ve been much harder on Keith who had to endure me constantly counting down or saying, “I don’t care about (insert whatever we were discussing here). I only care about making it to Hamilton, after which, I can die happy”. Keep in mind, we’re getting married in 2018.

A lot of my focus had been on the musical and rightly so but we were also going to one of the more popular destinations in North America. As amazing as Hamilton was (my review will be up in a separate post), I was blown away by Chicago. Pun very much intended.


Accommodation

I must give a shout-out to our amazing hosts, my uncle, Eric, his wife, Noel, and their effervescent daughter, Sophia. I highly recommend having relatives in Chicago, it makes travelling there so much more convenient and fun. We stayed over at their lovely home on North Lake Shore Drive, just a 10 minute walk to Wrigley and a 10 minute bus ride from Magnificent Mile. It was such a nice neighbourhood, we had a hard time leaving it to explore the rest of the city, or just in general, when it was time to go home.

For those of you who do not have relatives in Chicago, check out Airbnb. The hotel prices for the dates we were there were way too expensive.

​Getting Around

Now Torontonians or Chicagoans might gripe about their respective public transit systems, but let me tell you, after having had to endure the horrific traffic and abysmal state of public transportation in Manila, Philippines, twice this year, you guys have no idea how good you’ve got it. Sure there are delays, but the mere fact that you can get to your destination via bus or subway in less than an hour is a blessing, trust me.

We flew in to Midway Airport from Billy Bishop using Porter Airlines. As soon as we landed, we took full advantage of Chicago’s “L” trains and buses by purchasing a day pass using the machines at Midland station. With that, you can go pretty much anywhere you need to. I loved when the trains passed next to the buildings downtown. I’ve never seen anything like it.


Attractions

Since we were only in Chicago for such a short time, we had to maximize our sightseeing. After clearing customs, we took the Orange line straight to the Loop so we can go on an Architecture Boat Tour of the city. I highly recommend Chicago’s First Lady because it’s the only cruise partnered with the Chicago Architecture Foundation. Our docent was so funny and knowledgeable, it was the perfect introduction to this beautiful city and its rich history. I’ve heard great things about the other cruises as well, but we really loved the tour that focuses on the architecture, the why, where and how things were built. We also were able to walk the Riverfront, which I would advice people to do either before or after your tour.

We did the Magnificent Mile a couple of times by bus since the route going to my uncle’s took us through there. It’s worth seeing and you’d really enjoy it if you loved to shop, but we were saving all our money for Hamilton swag.

The second day, we woke up and walked to Wrigley Field. Despite being a Cardinals fan, even Keith had to agree how awesome it was that the park is very much just part of the neighbourhood. Plus the Starbucks across it had to be the coolest one we’ve ever been to.


The afternoon was devoted to Millenium Park and the Art Institute. We definitely did not have time to explore the park enough but I think we covered all the major works in the museum. Highlights include Seurat’s A Sunday Afternoon on the Island of the Grande Jatte, Chagall’s American Windows, and the Chicago Stock Exchange Trading Room. Do not miss the Thorne Miniature Rooms.


Then it was time for the main event: Hamilton at the Privatebank Theatre. Well worth the trip!

Obviously there are a lot more sights to see but those are what I would recommend for a short trip.

Food Recommendations

The best restaurant in Chicago was definitely my uncle’s kitchen. Him and his wife made us amazing food during our stay. But again, if you don’t have relatives that can serve you delicious free food, then here are some places you can try: For deep dish pizza, we had Lou Malnati’s which my aunt says locals prefer. Although our friend, Julissa, who is a local says she likes Giordano’s. Julissa also took us to Latinicity, an awesome food hall serving everything from $2 tacos on Tuesday to Peruvian Lomo Saltado. Worth a visit. If you’re ever near Wrigley, there’s a Mexican restaurant that we ate at after seeing Hamilton with incredible tacos al pastor, El Burrito Mexicano.


Souvenirs

Three words: Chicago Mix Popcorn


Final Thoughts

We loved our time in Chicago so much, even though it was barely two days, that we started looking at properties there. It was very much the US counterpart to Toronto in my opinion. I had never thought about moving to the States until Chicago. I can’t wait to visit again!

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One response to “Our Whirlwind Trip to the Windy City

  1. Pingback: The Best Christmas Gift I’ve Ever Received | Fashion, Food & the Fortress of Solitude

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