Prompt Images

For a frequent flier with a proclivity towards self-medication, there is no more important work travel task than finding the perfect pre-flight watering hole.

My favorite airport bar in the country serves no food and is usually too crowded for comfort.

It is stashed away behind a food court in a corner of Chicago’s Midway Airport, a spot inconvenient enough to weed out any casual fan of spirits and conversation.

On one February evening a few years back, I believe it was a Thursday, I was flying home from the Windy City** after a long week of meetings. When I approached the gate, I learned that my flight would be delayed at least an hour, so I searched for a place to park myself. After none of the chain restaurants caught my eye, I finally stumbled upon Reilly’s Daughter, a small Irish pub, packed to the brim with weary yet friendly patrons.

(** Fun Fact: According to the wisest Chicagoans the city gets it’s nickname not from the weather but instead from long-winded politicians. I have no way to confirm this but thought you should know.)

I made my way up to the bar and managed to find the only open seat.

After wedging my carry-on behind the stool, I asked the bartender for a food menu. Brendan O’Brien replied the same way he must have replied 100 times that day to 100 people making their first visit to the pub, “No food here, just beer and liquor, and we may have some wine.”

I proceeded to order a Guinness, the option closest to food, and began to take in my surroundings. There were a couple small TVs that were hardly visible, a digital countdown clock to St. Patrick’s Day, and maybe a hundred Polaroid photos of an older Irish guy with various Chicago celebrities.

“Who is that with Ryne Sandberg?” I asked Brendan, and he proceeded to tell me the story of Reilly’s Daughter. He told me about how his dad, Boz O’Brien, opened a Southside saloon in 1976, eventually selling it to move the establishment to Midway in 2002. He took pride in the fact that there are few airport bars in the country that are privately owned, and even fewer that aren’t connected to a franchise.

As a guy who enjoys a drink or ten, I typically don’t discriminate where and how I am served, but there is something to be said for the experience.

To call the personal vibe and welcoming ambience of Reilly’s Daughter “romantic” might be going down a road I’m not comfortable exploring (the destination rhymes with “nonalcoholic”), but fuck it, there is a certain romance to drinking in an establishment such as this.

After my Guinness, I ordered another, and then a Budweiser, and then ran out to the food court to snag a pretzel in an attempt to soak up booze before my flight.

While in line at Auntie Anne’s, the voice in the sky delivered the bad news: The 7:05 Southwest Flight to Boston would be delayed until 8:30. Carbs in hand, I made my way back to the bar and was able to reclaim my seat. “You trying to get to Boston too?” the businessman next to me asked. “Yeah, looks like we’re stuck” I replied. “Well… there are worse places to be,” he smiled as he took another pull from his beer.

The couple two seats down from my new friend was also heading to Boston, on a layover from a ski trip in Colorado, as was the attractive woman to my right, a pharma rep who looked the part and was putting a hurting on a series of martinis.

For the next hour, we swapped stories, told some jokes, and met Boz who had just arrived to work the night shift alongside his son.

With 15 minutes before boarding the skiers bought a round of Jameson shots for the bar, a toast to new friends and great service. As we tossed the whiskey back we heard the voice again, this time from an intercom in the corner: “Attention passengers, flight 2870 to Boston’s Logan Airport will be delayed another two hours, estimated departure time now 10:40.”

The bar erupted in celebration… and we kept celebrating.

The flight eventually took off and we all made it home, groggily nodding to each other as we deplaned in Boston and went on our separate ways, but acknowledging a connection that can’t possibly be made at a chain restaurant.

Mike Stiriti

Mike Stiriti once dreamed of anchoring SportsCenter back when that was a thing. Now he just tries to be funny.

learn more
Share this story
About The Prompt
A sweet, sweet collective of writers, artists, podcasters, and other creatives. Sound like fun?
Learn more