A Weekend in Chicago, Day 1

New Year’s Eve is always a fun time of celebrating with friends. However, this year, Drew and I decided to take a different approach. It had been months since our last excursion, meaning that we were far overdo for another trip. Not only that, but we still had several non-rev passes left to use before 2016 came to an end. Why let these discount passes go to waste?

Therefore, instead of rejoicing with our usual comrades within the familiar confines of Pittsburgh, we challenged ourselves to experience a new city.

Choosing which location could play home to our adventure was limited. Originally, we had dreamed of the warm tropics: limpid waves, tranquil sand, limitless sun. But fate (and American Airlines) did not deem this a viable choice. After that, the path became clearer. We could choose between Boston, Philadelphia, Charlotte, or Chicago.

While the other three cities were large enough that we could most likely find ways to entertain ourselves, Chicago was the home of Drew’s cousin. He would allow us to stay at his apartment, meaning that we wouldn’t have to waste money on other accommodations.

The choice before us was clear; a weekend in Chicago would be our destination of choice.

flight to chicago

The flight was an uneventful journey, direct and non-stop out of the Pittsburgh airport. We arrived in Chicago around noon on Saturday, December 31. This would be the perfect amount of time to spend some time exploring the city before the excitement of New Year’s Eve began.

Drew’s cousin’s apartment was located just a few blocks from United Center in Chicago’s Near West Side neighborhood. After settling in, we decided to peruse the surrounding neighborhoods and see just how many festivities we could get in while we waited for darkness to fall.

Our first stop was a bar called Kaiser Tiger. Renowned for its quirky atmosphere and wide selection of beers, Kaiser Tiger also had a hidden gem up its sleeve: curling. They had converted their outdoor beer garden into three small curling lanes, allowing patrons to practice their accuracy by hurling rocks into the bulls-eye target.beer at kaiser tiger

After nursing our first beers, we decided to look into the curling business to see if we could take part. Luckily, curling was free on New Year’s Eve. Finishing off our second beers as well as a delicious order of fries and garlic aioli sauce, we headed outside to see if we could jump onto a lane.

garlic aoili fries at kaiser tiger chicago

Unfortunately, we had completely missed the part about needing to sign up for a time. After talking with the hostess, we came to learn that the next available time was 3 PM. That was nearly 45 minutes away – what ever could we do until then?! Sadly, we were forced to get another drink while we waited.

Finally, our turn to play came around, and we headed into the wintry air. The game wasn’t quite like real curling – there were no brooms, and the court was half size at a minimum. However, the concept was the same, which meant we had to utilize strategies like blocking open lanes and then spinning the rock to get past these blocks.

Curling Lanes at Kaiser Tiger Chicago

In the end, we were two worthy competitors. It was a close matchup that ended in a 3-3 draw.

With no one being a loser, it was time to move on from Kaiser Tiger and continue heading down Randolph Street to our next establishment of choice – City Winery. This stop only lasted about a minute, as we quickly came to realize that we could not appreciate wine priced at $10 a glass. So on we went again, this time to Haymarket Pub and Brewery.

drinking beer at haymarket pub and brewing in chicago

After indulging in one of their specialty beers, we headed across the street to another pub which specialized in brews by 3 Floyds, Lone Wolf.

lone wolf 3 floyds brewing chicago

By this time, it is needless to mention our need for sustenance. We had successfully bar hopped the afternoon away and it was past time for dinner. We decided to stop at a well-known pizza establishment, Lou Malnati’s, in order to try the deep dish the city is famous for. It certainly didn’t disappoint, especially because we were seated in a VIP table next to a roaring fireplace.

lou malnati's deep dish pizza chicago

Eating and drinking to the points of excess has its limits, and we were feeling them. Though it was still quite early by New Year’s Eve standards, we knew that there would be no way we could make it to midnight unless we had a nap. Therefore, we returned to the apartment and laid down for just a few minutes…


We had alarms set throughout the evening to awaken us, but we angrily turned them off and crawled back under the covers. It turns out that going to bed at 8 PM after an afternoon of day drinking and expecting to wake feeling refreshed just a few hours later is not such a good plan.

happy new year in chicago

Eventually, we mustered ourselves out of bed around 11:30 PM. Our original plan had been to head into the city itself and join one of the numerous street festivities that was occurring, but there was simply no way this was happening now. Instead, we took to the streets of Near West Side and simply strolled around, looking for fireworks in the distance. As midnight struck, we were alone on a street corner, standing under the night sky. Cheers erupted from upper level apartments around us, but it felt as though we were distinctly separated from these groups. It was only us, together, on a foreign street in a new place, with nothing to hold us back.

Kristy Snyder

I'm a creative and quirky woman just looking to make her mark on the world. Writer, thinker, crafter, doer. Loves playing ice hockey and curling up with a good book. Traveling is a foremost passion and the road is always calling. Above all, I try to be an enjoyer of life.

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