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Join us September 10 – 13, 2026 in Chicago, Illinois for our 9th Annual Fall Retreat!

Escape the routine and embark on the ultimate dads’ getaway as we take our annual retreat to Chicago! This is always one of our favorite weekends of the year – a time to recharge, build new friendships and strengthen old ones, enjoy some amazing food and get some much needed time away!

Imagine a long weekend in Chicago where incredible food, iconic experiences, and brotherhood come together in one unforgettable retreat. By day, dive into Chicago’s legendary culinary scene with food tours through neighborhoods like Chinatown and Pilsen, taste world-class deep dish, and sip your way through local breweries and craft cocktail bars. Explore the city’s iconic sights—take an architectural river cruise, catch batting practice at Wrigley, or venture into unique experiences like axe throwing, comedy shows, or museum tours.

By night, the energy of Chicago comes alive. Share laughs over steak dinners and live blues, toast with your brothers at rooftop lounges overlooking the skyline, or have a cocktail one of the incredible local bars/lounges, like The Aviary or Three Dots and a Dash. And of course, there will be plenty of time to simply hang out.

We’ll be headquartered in the heart of River North, Chicago’s vibrant neighborhood known for its world-class dining, lively nightlife, and easy access to the city’s top attractions. From our hotel, you’ll be just steps away from steakhouses, rooftop lounges, art galleries, and the iconic Chicago Riverwalk.

On Friday night, your ticket includes an unforgettable evening at Avec, where Mediterranean-inspired dishes meet contemporary Chicago flair. Our group dinner will showcase chef-driven plates designed for sharing, paired with curated wines and cocktails, creating a warm, elevated dining experience in one of the city’s most acclaimed restaurants. Your retreat ticket also includes a special retreat gift, and all the behind-the-scenes insurance, planning, and logistics work to make this a fully curated experience – so you can just show up and enjoy.

For those who want to keep the night going on Friday, you can add on a 2-hour, open bar cocktail party after our Friday group dinner at the city’s famed tiki hideaway, Three Dots and a Dash—a true Chicago landmark and one of the top cocktail bars in the country.

Once you register, you’ll be invited into our private DMD Retreat Facebook group where you can start connecting with fellow attendees, coordinate activities, and make plans to maximize your Chicago weekend. We will provide a link with discounted rooms at our headquarter hotel as soon as it’s available.

Come hungry. Come ready for adventure. Most of all, come ready for fellowship. The DMD Chicago Retreat will leave you refreshed, inspired, and recharged for the year ahead.

We can’t wait to see you in Chicago!

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