The Broken Shaker (Freehand Hotel, 19 E. Ohio St., River North, 312-940-3699) has that kind of worldly, mysterious vibe you like to see in a hotel bar in the middle of the tourist-iest neighborhood in the city—it's the kind of vibe that will actually pull Chicagoans into the River North scene with nary a protest. The bar itself is a sibling to a hugely popular spot in Miami, but this place has more of a Midwestern twist to it. The rooms are dark and intimate (albeit decorated a bit on the strange side—yellow lights, kitschy wallpaper) but the buzz is surprisingly lively thanks to a monster Jenga set and a mixed crowd. There's actually a hostel inside this hotel, and you'll see plenty of travelers bearing the tell-tale backpacks among the bar's patrons.
The drink menu prominently features both Chicago–inspired cocktails (such as Da Mickey Finn Bird with hibiscus grenadine and Averna amaro) and hits from the Miami outpost (think banana rum Manhattan), and the mixed crowd happily guzzles them down late into the evening.
Here's what else we saw when we stopped in.