Sitting directly above The Bourgeois Pig Cafe on Fullerton, The Gatsby doesn't advertise itself and doesn't need to. Getting in involves solving a riddle that changes nightly and arriving with the correct password. The owner came up with this system themselves and, by most accounts, the whole ritual genuinely adds to the experience rather than feeling gimmicky.

The inside is layered. Candlelit rooms, antique portraits, velvet seating, and a soundtrack that shifts between jazz and big band. The decor was sourced from estate sales and vintage shops over time, which explains why the place feels assembled rather than designed. Multiple rooms mean you can tuck away from the rest of the bar if you find the right corner.

The Trinidad Sour is worth ordering. The bartenders are also known for making something off-menu if you describe your mood rather than naming a drink. One of the more consistently romantic spots in Lincoln Park, and not just because of the candles.