She worked as a waitress and as a cook in several fine-dining restaurants in Chicago, including at Trio, Schwa, and Alinea under Grant Achatz and Michael Carlson. In 2008, Regan began selling microgreens and vegetables at farmer's markets, soon expanding her offerings to include Pierogi. In 2010, she started a weekly supper club hosting 10-12 diners in her Chicago apartment. Through the supper club, Regan met several investors interested in supporting her opening her own restaurant. Regan named her restaurant Elizabeth for her deceased sister, opening in Chicago's Lincoln Square in 2012. Elizabeth features home-grown and foraged ingredients, originally served multi-course prix fixe menus at three 8-seat communal tables in the style of Regan's supper club. She later condensed the menu and removed the communal tables. The restaurant was immediately well-received, earning a Michelin star in its second year. Regan opened a second restaurant in 2017, Kitsune, with Japanese influences. It closed in 2019. She and her wife, Anna, opened The Milkweed Inn, in Nahma Township in Michigan's Upper Peninsula, in 2019. The Milkweed Inn hosts 10 guests each weekend April through October at $750 to $1000 per person for a "new gatherer" culinary experience. Accommodations include three rooms inside the inn, a platform tent and a small Airstream trailer. Regan plans to close Elizabeth once the inn is successful enough. A 2019 weekend "starts with pierogi and smoked lake trout on Friday and peaks on Saturday with a 15-course dinner that might include wild blueberries in juiced wood sorrel, young milkweed pods fried until the insides turn as silky as cheese, and moose tartare." She published a memoir in 2019, entitled Burn the Place. The New York Times called it "perhaps the definitive Midwest drunken-lesbian food memoir." In it she describes incidents "before she got sober 10 years ago, ran away from the police in handcuffs, had sex in bar bathrooms and used her car key to administer bumps of cocaine."
Recognition
In 2008 Chicago Magazine named her pierogi the best in the city. In 2016, Regan was named one of Food & Wine magazine's best new chefs. She was also named to the Crain's Chicago Business 40 Under 40. David Chang called her one of the best chefs he has ever known. As of January 2020 her restaurant Elizabeth had won a Michelin start six years in a row. Smithsonian named Burn the Place to their list of 2019's ten best books about food. It was one of ten contenders for the National Book Award for nonfiction, the first time a food book had been listed since a 1980 win for Julia Child.
Personal life
Regan is married to Anna Hamlin. They met while Hamlin was working with a wine distributor and managing the Elizabeth account.
