JONATHON: “Do you want to Uber there?”
ME: “…let’s take bikes.”
Chicago has a system of bike rentals spread throughout the city, much like Vélib in Paris or Citi-bike in New York. $10 for the entire day when used in 30 minute increments.
Five minutes later we were tearing down Michigan Avenue on hideous light blue beach cruisers with giant ads for Blue Cross / Blue Shield on the back wheel. Sunday morning, much like LA, is probably the best day to bike ride through the city because of less cars and a more relaxed energy to the city.
Nothing special to report from Doughnut Vault. It tasted like every other doughnut I’ve ever had.
But that didn’t matter because I was about to cross something off my sports bucket list – the Wrigley rooftops.
For those that don’t follow baseball, what makes Wrigley Field special is the atmosphere of the game. Right behind the stadium on Sheffield and Waveland Avenue are apartment buildings that have become businesses with kitchens, full bars, and bleachers on the rooftops. The last time I was in Chicago I sat near third base. This time I wanted the rooftops.
We rode our bikes three miles up Clark Ave in to Wrigleyville. I’ve never ridden a bike to a baseball game before, but now it’s my favorite way to get to a game. The ride became even better when I realized I had a bicycle bell near my left thumb that I continued to ring like a six-year-old while passing all of the fans at the bars.
At one of the stop lights, I pulled up next to a car with Cubs fans in the front and Phillies fans in the back.
ME: “I don’t want to alarm you, but there are Phillies fans in your back seat.”
HIM: [laughs] “Yeah, I know, they kidnapped me.
For someone that's not from Chicago, it feels like the Cubs are to White Sox, what the Lakers are to the Clippers. If you like the least popular team in town, you're just being a contrarian hipster donkey. So hashtag go Cubs.
A few blocks of bicycling later and there it was -- storied Wrigley Field. Here in this North Side neighborhood, the stadium stands tall yet unimposing, giving it the nickname, “the friendly confines.” With all of the people, the bars, the vendors, the hot dogs, and the singing around Wrigley – dare I say it’s even better than Fenway Park in Boston? It is. And Cubs fans aren't as abrasive as Red Sox fans.
We bought some Cubs swag at many of the independent shops on Addison St. and then walked over to our apartment building – Ivy League Rooftops. After several short sets of stairs, we had arrived. I walked over to the bar.
ME: We're here! Aren't you excited?!
HER: [laughs] We are here and it's beautiful day!
Darcy was a brunette with a red bandana and a compass tattoo on her right bicep. She was able to toe the line of tough and beautiful that every man there responded to. We talked briefly about our road trip and she became our go-to bartender for the rest of the game.
The Wrigley Rooftops are, simply put, the greatest summer BBQ ever. With the neighboring buildings literally within arms distance of each other, you can talk to other people, pass food to them, or even listen to the live jazz that was on the rooftop to our left.
We spent most of the game listening to said jazz, chatting with Darcy, or talking to two sixty-year-old Phillies fans visiting from Delaware for their first Wrigley rooftop game.
Unfortunately the Cubs got slaughtered 11-5, so we didn’t get to sing the terrible but catchy song they play whenever the Cubs raise the white “W” flag after a win. Because of that, I'll make it "Today's Song" so you can hear it below (and preferably sing it with 41,000 of your closest friends).
If you’re a fan of baseball, or fun in general, the Wrigley Rooftops are a must.
I met Margaret at a hostel in Paris in 2011. She was cute and English-speaking, and I overheard her asking the front desk about a show at the Palais Garnier. A few hours later we were wearing our backpacker's finest clothing and watching the symphony together. Over the years we've kept in touch via Facebook and since I'm in Chicago, we decided to meet at the fabled comedy club, Second City. She chose the show "#DATEME, an experiment with OK Cupid" because she's read my dating articles and she said, "I knew you'd like it." She brought along her friend, a tall, vegetarian, luddite, badass, named Caitlyn, and together we made the super attractive people you see in the photo above.
After the show, we went to a rooftop bar in Old Town and chatted about travel and Chicago dating scene. Jonathon privately made the astute observation about Margaret that she “engages people with her eyes, which is a good quality for a leader.” He’s right.
An Uber later we were back at our hotel, and I could already feel the end of my road trip coming near – tomorrow would be my last full day in Chicago.