Chicago has been on my travel list for a long time, but I never got around to going. It’s a city full of history, art, sports, and food — everything I could want in a vacation other than a few mountains, but I can overlook that last point. My American friend in Taiwan visiting home for the first time in three years provided the excuse I needed to finally visit the Windy City.
I was concerned about booking the trip — flights from Newark are usually reasonable, but hotels around the US have gotten exorbitantly expensive over the past several years. Last year, I planned a long weekend in Chicago only to find that the cheapest hotel downtown was just over $300 per night. Fortunately, I found many more hotels at reasonable prices this time around, but because I didn’t know what neighborhoods were good, I ended up spending a little more to stay in the Loop at Club Quarters on Whacker.
The hotel was pleasant — kind of no frills and small rooms, but comfortable and quiet. Most importantly, Club Quarters on Whacker is convenient. The hotel is near public transportation, museums, and the architecture cruise dock. Plus, it’s pretty easy to find when the city is unfamiliar. Walkability is a primary concern for someone uninterested in taking Uber, which I only considered taking once when I noticed a sign about service disruptions on the train to O’Hare Airport (I risked the train, and there was no service disruption).
Arriving in Chicago was a breeze. I had an early flight out of Newark, which meant I arrived mid-morning. As it was a short trip, I only had my backpack and made my way to the Blue Line train — it was a longer-than-expected walk across the airport, but it is a much less expensive option to get into the city.
The downside to getting a multiday pass at O’Hare Airport is that you can’t purchase the 7-day pass; the most you can get is 3 days (and I needed 4 days). A 3-day pass is $15, while 1-day is $5 and 7-day is $20. To put that into perspective, the train from the airport is $5, and each trip on the L is $2.50. It really wasn’t difficult to get my money’s worth out of the unlimited transportation passes. I’ll admit that the L isn’t always safe — I witnessed an unprovoked attack on my last day and noticed numerous vagrants on the trains at other times. That being said, it’s no worse than the NYC subway. My former coworker who moved to Chicago said that it’s safest to get on the first car with the conductor, particularly in the evening. On my last day, I even found a helpful station attendant who helped me get the one-day pass after my three-day pass expired on arrival (she checked and said I had about 20 minutes left on it).
Yes, Chicago, in many parts, is a gritty city. There’s a reason Christopher Nolan chose to film some of the Batman movies there. Even within the Loop, which is more touristy, the city doesn’t always appear pleasant, but I never felt unsafe (though that feeling is relative considering where I’ve lived and traveled).
Seeing the Sights of Chicago
I was more prepared than usual for this trip. I knew there was a lot to see and do around Chicago, so I had to prioritize and plan the itinerary. Museums to visit, architecture to see, breweries to try, and food to eat — it was a lot to pack into four days. Add all that to the Devils in town for a game against the Blackhawks and an opening-weekend game at Wrigley Field before my flight home, and you’ve got one busy trip in a major city.
The first day was reserved for museums, which were near the hotel. I got lucky at the Art Institute of Chicago — there was a protest outside, so I missed the sign that the Salvador Dalí exhibit was sold out for the day, and the ticket clerk felt bad and gave me a free ticket to the rest of the museum.
I knew I’d love the Art Institute, but I didn’t know just how much. I had actually forgotten the scene in Ferris Bueller’s Day Off at the museum (it was a cheesy ’80s montage with masterpieces in the background). There were so many wonderful works of impressionists to gawk at. There were also some interesting artworks that I knew nothing about, like Henry Fuseli’s depiction of John Milton dictating Paradise Lost to his daughter — Milton looks like he’s already dead rather than blind.
It’s a large art museum, and I wandered through for a lot longer than anticipated. There was so much to see that I almost missed the Chagall Windows — staff pointed me in the direction as I asked directions as I thought I was ready to leave.
Rather than head to the Field Museum, I walked through the park with a stop at Lake Michigan. I was still tired from the early morning flight and needed something a little more relaxing. I wanted to try the architecture cruise, but found that it wasn’t yet open for the season (had to wait a day). I was able to walk along the river and take in the sunny views of the city. The excursion left me close enough to the hotel for a quick nap and coffee before heading out for dinner, drinks, and exploring.
The next day, with my friend coming downtown, we were able to take the architecture river cruise — it was the first day of the new season for the cruise, which would’ve been good to know the previous day to avoid checking in to try to go when it wasn’t running, but I digress. We had enough time before the cruise for my first taste of real deep dish pizza, which I still say is not pizza (it is good though).
The cruise, which was well worth the time and money, was followed up with more architecture sightseeing at the Rookery, which can’t be viewed from the river. It’s an amazing work of art from the inside, but isn’t impressive outside.
After all the art and architecture downtown, I took a day in Oak Park for a view of the Frank Lloyd Wright houses. Unfortunately, early spring is not the best time to visit as the neighborhood tours are not running — there’s a guided tour of his house and studio, and they provide a neighborhood map of other houses Wright designed. I was also able to take a tour of the Ernest Hemingway birth house nearby. It’s definitely a neighborhood that requires a little more planning than I put into it, but it was well worth the journey.
There were also trips to breweries in the former factory/warehouse areas that are now upscale, hipster-like neighborhoods. Some of those breweries were good, while others were mediocre at best. The only thing I regret is stopping at a distillery and ordering a flight of Malört. I understand it’s a Chicago thing, but it’s not something I ever want to taste again.
Walking around those neighborhoods was fun — I had, unfortunately, wandered through them later in the day. It was not exactly warm in early spring as the sun set, so it limited my time outside. I’m sure a month after my visit it would be much more pleasant for walking.
The only disappointment with the city is that the Loop is almost a ghost town after work. They constructed some huge residential buildings, but there isn’t much for the residents to do in the area — there are a few nice restaurants and bars, but not much else. This is an issue with a lot of downtowns; they exist only for work.
There was plenty more to see in Chicago, but with only four days (two of which were short), it was impossible to see it all. But getting a taste (both literal and figurative), provides me with greater incentive to revisit and explore the Windy City.
Have you visited Chicago? What were some of your favorite places?
