Our Red Sox-Cubs 2022 Diary

The breakdown of our Wrigley Field adventure.


To start the month of June, the Boston Red Sox continued a series of road games in Chicago — playing the Cubs for only the third regular-season series between the two teams at Wrigley Field.

Starting next year, it looks like every team will be playing every team and interleague play is significantly less special — but this is still a big deal for now. Two of the most storied franchises in baseball history who never ever play each other, doing it in one of the most revered ballparks in the game.

We knew it was special, so The Girl Who Loved Nick Pivetta and I planned a trip to the Windy City for the holiday weekend. Red Sox at Wrigley, plus all of the other tourist stuff we could squeeze in.

Here’s a recap of our trip:

Thursday, June 30

After work ended on Thursday, we jumped on the Light Rail to BWI Airport. We got there with plenty of time to spare, so we did some airport exploring and decided on Mexican for dinner. No frozen margaritas, if you can believe it.

All was going smoothly until it was nearly time to board. I didn’t know that Southwest had open seating. In fact, I didn’t know Southwest was even considered a budget airline. I just chose them because their flights worked for our schedule and went direct to Chicago.

Needless to say, The Girl Who Loved Nick Pivetta was not happy when we discovered that being in Boarding Group C almost certainly meant sitting apart. A few puppy dog eyes later and I was at the gate asking about an upgrade.

“Yeah, you’ll definitely be sitting apart,” said the Southwest gate attendant, “We usually joke that Boarding Group C stands for ‘Center Seat.’”

“Sounds like it stands for ‘Credit Card at the Gate,’” I said only half-joking.

$60 bucks got us the honor of being the first two people on the plane. The flight went well, we landed in Chicago with no problems, Ubered to our Airbnb, and tucked in as it was already late and we had an early morning.

Friday, July 1

We woke up only a five-minute walk from the ballpark, but still wanted to get up early to explore. Wrigley’s 1:20p Friday games mean the gates open at 11:20a, which means breakfast and shopping starts around 9a.

We walked towards the park and found Do-Rite Donuts & Chicken across the street. I could get used to spicy chicken sandwiches for breakfast right before a weekday matinee game. Scarfed down a Boston Creme in honor of our team and then did some exploring around Wrigleyville.

When the gates opened, we headed inside for a little batting practice. I came two seats away from a Bogaerts BP ball but missed it. Otherwise, BP was quiet. We used the other hour we had to pick up some Chicago dogs which are…out of this world. I’ll get into my thoughts on deep dish later, but I’ll tell you right now that Chicago knows how to do wieners…

For the uninitiated, a Chicago dog consists of mustard, onions, relish, tomato wedges, pickle spears, and celery salt — all on a poppyseed bun. It’s basically all the things I like on dogs, so I got hooked. I probably ended up eating a dozen of them over the weekend.

Game 1 started with a bang. Jarren Duran hits a homer on the first pitch. Raffy misses a back-to-back homer by going five feet the wrong way of the foul pole.

But that was pretty much where the fun ended. We enjoyed taking in our first game at historic Wrigley Field, had a couple cold ones, sang ‘Take Me Out to the Ballgame’, but the game was rough. Hansel Robles blew another save and future Red Sox setup man David Robertson closed the door for the Cubbies.

Since we figured it would be the only loss of the weekend, we thought if there was a time to pretend to drown sorrows, it would be now. So we decided to bar hop around Wrigley.

We started at Lucky Strike Wrigleyville for some brews and bowls. The Girl Who Loved Nick Pivetta bowled her personal best in the first game, while I focused more on the brew aspect of the stop.

We then moved on to the least sports bar-y of them all, an organic brewery called Greenstar Brewing. Their on-tap sour was delicious, so I was really tempted when the bartender asked me if I wanted another, but we promised to only do one drink at each place because we wanted to hit a few joints. But she was kind enough to suggest some other places to hit, including another bar she works at.

We headed over to that place for some Old Style and ran into that same bartender, who I guess was getting off at one place and clocking in at another. Respect the hustle.

Stopped for some more Chicago dogs, because I couldn’t help myself.

Another bar for Old Style.

The Girl Who Loved Nick Pivetta can’t eat hot dogs, so we made a pit stop at Cane’s (which we call Raising Cane’s in this part of the country) for some chicken.

We then headed back to our Airbnb to shower and change before going back out for our final event of the day: The Neo-Futurist’s ‘Infinite Wrench’, an hour-long theatrical event where they attempt to perform 30 short plays in 60 minutes. We’ve seen the show in New York and have been wanting to see the Chicago version. Always a blast, we enjoyed our time and called it a night.

Saturday, July 2

Saturday had the rare night game at Wrigley, so this was only daylight we had to explore the city.

After sleeping in, we took an Uber down to the Chicago Bean, looked at it, and said, “Yep, there it is.”

Many Red Sox fans must have had the same idea, we saw a lot of Sox shirts and caps. I love deep-cut jerseys, and the Mike Carp jersey I spotted really threw me back.

We wanted to Citi Bike around the water, but the Citi Bike thing took my seven dollars.

After walking a few blocks down to a restaurant that ended up being closed, we walked past the theatre district’s marquees, and headed into the tourist trap Giordano’s for some deep dish.

What I didn’t know is that the pies take over an hour to cook, so we enjoyed our drinks at the bar knowing that our afternoon was quickly wrapping up if we wanted to make it back to Wrigley for gate time.

My verdict on deep dish: It’s good, but it isn’t pizza. NY Style all the way.

We headed back to Wrigley. Our goal on this day was autographs, and The Girl Who Loved Nick Pivetta got Matt Strahm to sign her ballcap. Nice guy. He was signing for any fans that wanted one all weekend.

After that, we grabbed our Oatly ice cream in the collectible helmet and found our seats near the press box. We were seated on the two sides of a giant pole — welcome to Wrigley Field. Our seats were in “pole position” according to the Cubs fans across the aisle. Cute.

This game was even worse. Josh Winckowski looked solid, but a couple of errors were the difference-maker. Future Red Sox setup man David Robertson closed the door for the Cubbies again and all of a sudden we had lost the series.

We went to bed early, too dejected to even eat our deep dish leftovers. It was too Chicago. So we got Taco Bell Cantina instead.

Sunday, July 3

I woke up the next morning to see that Winckowski had called Wrigley “stock standard” and I knew that today was going to be a good day. Guy’s been in the league for five minutes and he’s already shit-talking the mausoleum that is Wrigley Field. We can’t possibly lose today.

But first, more chicken and donuts.

We tried for more autographs. Strahm came over again (nice guy!), but we already had his auto, so we kept waiting. Chaim Bloom came over and added to Taylor’s cap (I asked him to take a couple Cubs guys with him and he laughed diplomatically), but that was it for signings. No batting practice that day so it was quiet.

This game was obviously the best of the three because the Sox won, 4–2 in extras. When the Sox had the lead after seven, the crowd thinned out quite a bit so we took it upon ourselves to upgrade our seats.

That’s when some Cubs fans showed their true colors. As the game went into extra innings, beer hadn’t been served in a few hours and people started to sober up. Turns out the “Friendly Confines” are a lot friendlier when people are drunk and the Cubs are winning.

Since the game ran long, we had to shower quickly to get ready for the final thing on our itinerary: a trip to Steppenwolf Theatre. The Girl Who Loved Nick Pivetta has been a fan of a few of their artists for a while now and the ensemble company is sorta the mecca of Chicago theatre. Although the main focus of the trip was baseball, we saw some excellent shows and Steppenwolf’s ‘Choir Boy’ was no different. It was a great way to wrap up our trip.

We Ubered home and packed it in right away because had an early flight.

Monday, July 4

The alarm goes off at 3:30a. At 4:00a, we’re in our scheduled Uber headed for the airport. We got Dunkin’ on the other side of security and waited for our flight. We’re in Boarding Group A this time, so no credit card at the gate.

After a few typical delays, we made it back to Baltimore.

But because we’re maniacs, the baseball wasn’t over yet. We added a thirty minute nap to our four hours of sleep and then headed back out to Camden Yards to see some Fourth of July baseball — Orioles vs. Rangers.

And the Orioles looked stronger than the Red Sox.

We left that game early. A little baseball-ed out, a lotta too hot, and no sleep made it an early night for us.

But a trip we will never forget.

Want to chat Red Sox? Check out Bleacher Brawls.

Want to chat baseball? Email me: theboywholovedjoekelly@gmail.com

Want to keep updated with the column? Find it on Instagram @theboywholovedjoekelly and Twitter @boywholovedmlb



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Patrick J. Regal

Patrick J. Regal

Educator. Artist. Founder and Editor of Feature Presentation. Instagram: patrickjregal