My Chicago: Billy Lawless

The owner of Henri, The Gage and The Dawson spills his Chicago secrets.


They say the Irish love a good story, and boy, does Billy Lawless have one. A business opportunity that went south in Dubai led the Galway, Ireland, native to—of all places—Chicago, where he became the successful owner of two bars: the Irish Oak and The Grafton. Years later, he set his sights higher on the epicenter of the Windy City: The Mag Mile. With three restaurants in his stable, the larger-than-life expat is easy to spot by his Disney hero stature, immaculate suits and classic Celtic charm. He reflects on why Chicago loves the Irish, and why he never looks back.

Billy Lawless
Billy Lawless (Anthony Tahlier Photgraphy)

How many years have you been in Chicago?
Moved here nearly 16 years ago

How and why did you make it your home?
Well I ended up here by default, was meant to move to the Middle East to open a restaurant venture in Dubai. At the same time my father was moving here to open an Irish pub in Wrigleyville, (mid-life crisis I think) but he decided to move here anyway. My deal fell through and I did not want to stay in Ireland so need up immigrating here and opened up the Irish Oak.  My mom is still in shock over her move here! But the folks are still together!

Why is St. Patrick’s Day such a huge deal in Chicago?
The fact that Chicago is enamored by St Patrick’s Day stems back to the early arrival of Irish immigrants here in the 1800s. Life was incredibly harsh and unwelcoming here for the Irish back then. Consequently they strove to assimilate by immersing themselves in the civic and political fabric of Chicago.  As a result still evident today, Irish Americans are still very prominent in all aspects of Chicago life—politics, police, fire department, etc.  The great Irish communities of Beverly and so forth and consequently their traditions took hold. The plumbers union still upholds and drives the annual St Patrick’s Day parade. Plus people love to think they can drink more than the Irish!

What are some of the wackier, but PG-stories, that you can share about working during St. Patrick’s Day?
Well one woman once got incredibly irate with me because she was convinced I was not Irish and only faking an accent. Her reasoning: “Your teeth are too white to be Irish.” Nothing like a good old stereo type for St Paddy’s Day. Obviously she was slightly impaired.

You’re a fixture in the local Irish community. What is it about Chicago that keeps expats here?
Chicago is a very vibrant City with varied and vast cultural identities and endeavors that make it a very livable place.   

What food do you miss from home, and what dish/restaurant reminds you of it?
I don’t miss any food from Ireland.  But if you want a great Guinness and fish and chips you are very welcome at The Gage.

How would you describe your (semi) new venture Dawson? What makes it different from The Gage?
The Dawson is a fun bar restaurant with great cocktails, craft beer and food. We are definitely very American focused compared to the Gage which is more of an European gastropub. Once the weather cooperates, we will be opening the Dawson beer garden which will be a great respite from the daily humdrum of life.  

What restaurants, attractions and events do you like to hit on your days off?
My day would never be complete without starting with a cortado at La Colombe, a touch of hot yoga preferably with my wife if our schedules permit and once in while I love to hit the Russian Bath house on Division for a super hot steam and a lashing of eucalyptus branches. Restaurant wise—I love a late-night dinner at Avec and a closing cocktail at Barrel House Flats again when possible. It’s always more fun with my wife!

My Perfect Day

Start with a sweat
Hot yoga with David York

Fuel and caffeinate
Cortado and sticky bun at La Colombe

The good life 
Lunch at Henri: glass of bubbles and a dollop of caviar

Culture walkabout

A stroll through the Modern Wing of the Art Institute  

Hipsters and hamburgers
Evening snack at Au Cheval

Fresh catches
Oysters and dinner at the bar at Shaw’s Crab House

11 pm 
Never a drag
The Baton Club for cabaret