COUNTRY VS. TOWN: JACKIE FLAHERTY

JACKIE FLAHERTY grew up in Palos Park in a supportive, close-knit household where hard work was valued and dreams, big or small, were always encouraged. She attended Mother McAuley and truly loved the all-girls environment, which shaped her confidence early and taught lessons in how to be both outspoken and collaborative.

At the University of Illinois in Champaign, Jackie had the quintessential Big 10 college experience which gave her a surprising amount of real-world education in responsibility, time management, and reading people. She went on to earn my master’s in counseling, completing her practicum and internship at the University of Chicago’s career office.

“I loved working with students to help them prepare for interviews and navigate early career decisions. That experience led me into recruiting in trading and financial services, fast-paced and complex environments that required strong listening skills and an ability to match people with the right opportunities,” Jackie says.

Travel was always in the background. Jackie studied abroad in Florence, her first time in Europe. She recalls the experience as humbling, unforgettable, and transformative.

“I learned how to be resourceful and In her twenties, travel was often about quick escapes, not because she preferred it that way, but because it fit the busy season of life when PTO was limited and trips were often built around weddings, weekends with friends, and whatever life placed on the calendar. Jackie explains, “That constraint followed me into adulthood for a different reason. Even when you have the means, time is rarely unlimited. That’s at the heart of my travel planning business, The Weekend Discovery: designing extraordinary travel that fits beautifully

The skills Jackie picked up recruiting in trading and financial services required sharp listening, discernment, and creativity. She learned to understand what people truly needed, even when they weren’t sure how to articulate it.

Jackie explains, “That translates directly to travel advising. Matching a client with the right hotel or designing program. Helping people figure out what they want, even when they’re not sure, is still at the center of my work.”

Her life now looks nothing like those corporate years. She runs her business with a small but mighty team and finally has the flexibility to be present for school pickups and drop-offs; a luxury corporate life did not provide.

“Everything I do blends work and life in this intentional, rewarding way. When I travel, I’m always in research mode, noticing closet sizes, the energy of a lobby, and the way a property handles service, amenities, families, and details that matter. It’s all about placing clients exactly where they belong,” she says.

She relishes building genuine connections with hoteliers and partners around the world, calling it one of the most rewarding parts of the job.

“I care about every trip as if it were my own. While anyone can book online, what they can’t get is personalization. The birthday remembered, the allergy flagged, the bottle of Chablis instead of Champagne, and the right room type for a complicated family dynamic. Now I get to share that world with my two daughters. They love travel in the most joyful, imaginative way. They even play “hotel” at home. There is nothing funnier or sweeter than two tiny butlers running around the house announcing that our room is ready,” Jackie says.

What’s on your reading stack? Autobiographies. Right now, Be Ready When the Luck Happens by Ina Garten and The Third Gilmore Girl: A Memoir by Kelly Bishop. What organizations do you support? I’m drawn to people who are building something, especially women stepping into a second or third act of entrepreneurship. I believe in connecting people, sharing networks, and creating opportunities for others to succeed. This community supported me when I launched The Weekend Discovery, and I take every chance I can to pay that forward, whether it’s cheering on a new business, making an introduction, or quietly supporting someone pursuing a dream.

What’s your signature entertaining style? Comfortable, unfussy, and always welcoming. If the door is open, you are invited. I love the kind of gatherings where people relax right away, kids wander in and out, and the champagne is already flowing before anyone has even taken their coat off. I also love the nights when noticing. The goal is simple: good energy, good company, and the kind of gathering that keeps unfolding, one more glass, one more story, one more hour.

Favorite winter tradition or activity? In Hinsdale, winter is all about finding warmth. I am happiest when I can settle in near a great fireplace or escape somewhere cozy for a long dinner with friends. And when the cold really settles in, my favorite tradition is planning a warm-weather getaway to look forward to.

Go-to outfit? Jeans, a sweater, and flats of some kind. I walk too fast for heels. Is there anything you can’t leave the house without? My phone. I know, I wish it wasn’t the case, but here we are. A lip balm and a pack of UNO cards. UNO solves almost everything when you’re with kids.

Where do they know you by name? Hotel sales directors. We exchange countless emails to ensure everything is prepared for a client’s stay. Occasionally, someone will say, “Oh, I’ve heard of The Weekend Discovery,” and it absolutely makes my day. I’m an introverted extrovert, so those moments feel both surprising and incredibly meaningful.

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WHEN IN COUNTRY

A perfect day in the country is? A walk into town for coffee and quiche at Toni’s, plus a cookie or sweet treat for the girls. Browsing local shops and picking up something fun at Vintage Charm or My Sister Kate, then lunch at Fuller House. By late afternoon, we are usually back on our block, which honestly feels like childhood in the best way. Kids are everywhere, darting from yard to yard, ringing doorbells, inventing games on the fly. The older kids somehow end up in charge, the little ones try to keep up, and it is genuinely the best entertainment to just stand there and watch it all unfold. Neighbors gather out front, someone asks what everyone is making for dinner, and half the time we end up laughing because no one has a real plan yet. Then we head inside, turn on the fireplace, and end the night with a movie or a board game.

WHEN IN TOWN

A perfect day in town is? In Chicago, my perfect day depends on the season, but I will always support a staycation. In the winter, that looks like checking into The Peninsula, then heading to the Art Institute for a quiet morning wandering my favorite galleries before the crowds arrive. Lunch at The Gage, an afternoon of shopping and strolling Oak Street, and then cocktails and dinner at RL to wrap it all up.