Humor Travel Life
For someone who loves to travel, it’s especially thrilling to share that your latest trip resulted in getting engaged. And that’s just what happened during my trip to Midwest for the holidays.
After spending last Christmas in LA, Tyler and I planned to visit our respective homes for the holidays. I’m from Grand Rapids, and he’s from Chicago - two cities that are roughly a 3-hour drive from each other. This meant that visiting our families in one trip is a pretty easy endeavor.
Our Christmas vacation didn’t exactly start as planned though. A family emergency forced me to travel more than a week earlier than I was supposed to. Despite a scary close call, everything turned out okay. Though I was in and out of the hospital, I was still able to show Tyler around town. I took him to the Grand Rapids Public Museum, ice skating, downtown, and had him meet some family and friends.
After Christmas, it was time to head to Chicago to see Tyler’s family. He showed me where he grew up, went to school, used to work, and more. He even took me to see the Home Alone house! Fun fact: the Home Alone house is in Winnetka, just outside Chicago.
Though we spent the majority of the week in the suburbs, we had planned to spend New Year’s Eve in the city. Tyler booked a reservation at the Drake Hotel. This hotel is a famous hotel in Chicago and is absolutely gorgeous inside. The name ‘Drake’ is also a Seinfeld reference, and since Tyler and I are both fans of the show, it was a perfect fit for our big NYE in the city.
We arrived in the city in the late morning, first heading to the Christkindlmarket at Wrigleyville Stadium. While the main market location at Daley Plaza had already closed for the season, the Wrigleyville one was still open. It was smaller than we thought it would be but still cute to see. They had ice skating, a massive Christmas tree, and vendors selling food, over-priced hot drinks, and winter accessories. We chatted with Tyler’s friend Johnny for a bit and then left the market to go check in at the Drake.
Being in Chicago around the holidays - and especially staying at a hotel like the Drake - felt like my own version of Home Alone 2 when Kevin stays at the Plaza Hotel. The Drake was busy too, as the hotel was hosting a fancy New Year’s Eve party later that night.
After check-in, we both got ready for dinner and then headed out. We wanted to go somewhere that felt special to Chicago and was close to our hotel. We decided on Harry Caray’s 7th Inning Stretch, a cool sports bar and restaurant in the Water Tower Plaza. We had made a 5:45 reservation, but we were both really hungry so we decided to see if we could get seated earlier. It was a good thing we did because we had no idea the restaurant was closing at 6! We still had enough time for a nice dinner though. Tyler ordered a veggie burger, I ordered a chicken Caesar salad, and we both got a beer.
During dinner, though, Tyler began tearing up a bit. My natural instinct was that something was wrong and he was worried about other things going on at the time. I would shortly learn, though, that the sentimental tone was for an entirely different reason.
Once we finished our meals, we went to the nearby Hancock Building to see if we could look at some high-top views of the city. I had previously gone into the Hancock on St. Patrick’s Day in 2019 to catch the views during the day. Fun fact: the women’s restroom at the Hancock has the best views of the city and lakeshore. Unfortunately for us, the Hancock decided to close all their windows so you couldn't look out. Not sure why they did this on NYE of all nights, but nevertheless, it was a bit of a bummer.
We continued to walk along the Chicago streets near our hotel, taking in all the beautiful Christmas lights on display. Seriously, Chicago may be very cold this time of year, but it’s absolutely stunning with the Christmas lights. I would absolutely recommend seeing Chicago during the holiday season in a heartbeat.
At one point, Tyler suggested crossing the street to where the historic Chicago Water Tower was located. I remember seeing this before when I visited in 2019 and thought it was very beautiful. It’s a water tower that looks more like a historic church or small castle.
I walked up to the Water Tower with Tyler, noticing all the Christmas lights surrounding it and complementing how romantic it looked. As we walked alongside the tower, Tyler began telling me its history and then spoke about our relationship and that he wanted more. It was then that he got down on one knee and said “Jill Marie Zwarensteyn, will you marry me?”. I just remember being in a state of happiness and shock as my hands were over my mouth. I was smiling, crying, and I kept trying to get out a ‘yes’ - though I know for sure I was able to manage a head nod. It’s funny how these moments almost feel like a dream.
The proposal was incredible though! And the Christmas lights all around made it perfectly romantic. For any fellas who want to pop the question, I'd say the Water Tower at Christmas is one of the best places to propose in Chicago.
Tyler then got up and placed the ring on my finger. Shortly after, a cop came over and said to us “I saw the whole thing. I hope you said yes. Would you like me to take a picture?”. We were very grateful since we didn’t have anything else with us at the time to take photos.
The first people we called were our parents. My mom said she had a gut feeling she knew what my good news was. Moms always have a way of knowing that stuff.
After getting off the phone with our parents, a couple of girls came over and asked us if we wanted them to take a video of us reenacting the engagement. Now, here me out: I’m all for couples recording their engagement, but the idea of us reenacting it for video content made Tyler and I squirm. We politely declined, and eventually started making our way back to the hotel.
I'd describe the newly-engaged feeling as similar to booking a fabulous acting job. Dancing around, jumping, smiling, telling random people the good news - yeah, it’s a lot like that.
Needless to say, I was that girl - crossing Chicago intersections holding up my hand shouting “I’m engaged” in front of people who I’m sure could care less.
Do you ever hear about those couples who get engaged and get free champagne or something? Yeah, we didn’t get that. Once we got to our hotel room we officially put the word out to more of our family and friends, eventually watching the ball drop on CNN as we rang in 2022.
Need to say it was my most memorable trip to Chicago ever.
About the author
Jill Zwarensteyn is a writer and comedian who has been featured on Amazon, truTV, The New York Times, Matador Network, BUST Magazine, Sleep Advisor, Tiplr, ARTRPRNR Magazine, YourTango, Thought Catalog, GoMad Nomad, Mashable, The Daily Mail UK, the Cannes Film Festival, LaughFest, Women's Lifestyle Magazine, and the Funny Women Festival LA. For more info visit: http://www.jillzwarensteyn.weebly.com