Our first stop has us hanging out in the lobby of the Lawrence House, a 1920s hotel turned apartment complex. This isn’t your ordinary apartment building, however. Occupying a small space in that lobby is Larry’s. The owners of Heritage Bicycles opened this gem in February of 2017, and patrons have been grabbing a craft cocktail or cold one and making themselves comfortable in the Lawrence House lobby ever since.
The lobby itself is a large, open common space for use by residents of the apartment building and bar patrons alike. Leather sectionals, armchairs, and oversized tables with study lamps make the room a perfect place to sip a cocktail and get some work done, or simply indulge in conversation under a beautiful stained-glass dome ceiling.
For a more intimate setting, snag a seat at inside Larry’s— which is cozy, rustic, and bathed in red light for a moody vibe.
As far as drinks go, we went with the namesake cocktail. The Larry is a single-barrel Elijah Craig salted coffee old fashioned, and it did not disappoint. Based on that drink and a perusal of the menu, Larry’s has a penchant for brown liquors.
That said, the cocktail list doesn’t discriminate; you’ll find drinks that feature everything from bourbon and rye to gin, mezcal, brandy, and more. Our round two choice was the Illegal Smile. Mezcal forward, the fresh lime lingers in a good way, and it reminded us a bit of a mezcal margarita.
Right down the street is the main event of the night. We’re finishing things off at the famed Green Mill Cocktail Lounge for live jazz and dancing. 
This storied club has seen more than its fair share of jazz legends, swing dancers, mobsters, and slam poets throughout the years. Originally named Pop Morse’s Roadhouse in 1907, it was renamed Green Mill Gardens in 1910. During prohibition, a member of Capone’s outfit became a co-owner of the joint and bootlegged out of the club.
Capone himself would frequent the Green Mill, and you can still see his booth when you visit—it’s the only one with clear views of both entrances. After prohibition, the club became more dignified, showcasing famous jazz musicians and singers, like Al Jolson and Billie Holiday.
The Green Mill is also home to the longest-running poetry slam in the country, The Uptown Poetry Slam. But tonight, we’re not here for poetry. Tonight, we’re here to dance to the big band jams of yester-year, courtesy of the Alan Gresik Swing Shift Orchestra.
Gresik and his band have been house favorites at The Green Mill since 1998, playing vintage-style big band of the 1930s and ‘40s from 9pm to 1am every Thursday night. Part of their show is styling it as a live vintage radio show, complete with the hosts/singers reading scripts to silly vintage-style radio commercials. And when the music is playing, the dance floor will be packed.
But don’t be intimidated by the folks who clearly know how to lindy-hop to the hits around here—everyone is always very welcoming to swing pros and rookies alike. If you’re lucky, someone who knows the steps will ask if you’d like to dance and can teach you the basics. Otherwise, just get out there and have fun.
If dancing isn’t your thing, wave down a server or make your way to the bar and order yourself a drink. There is no cocktail menu. And there’s certainly no pretention. Everything is cash only and priced to sell, but always well done. Your best bet is to keep it simple—stick with classics. The bartenders are notoriously terse and always busy, but they’re well-versed in their craft. PSA: don’t even think about asking to see the prohibition tunnels behind the bar (the answer is always a hard no).
Things you should know before you go: The Green Mill is CASH ONLY–and there is an $8 cover for Thursday nights. Also, Alan and his band are quite popular, so if you’re looking to snag a seat—whether a booth or bar stool—it’s worth arriving by 8pm.
If you don’t mind standing, wander in whenever it suits you… the band plays until 1am. If you arrive late, you’re lucky, and your party is small enough, the staff may squeeze you into a booth or table with some strangers/new friends. Either way, standing, sitting, drinking, dancing: if you’re at the Green Mill, it’ll be a good time.