We heart this classy little Italian enoteca on the Hubbard Street strip — and not just because it's affordable. The atmosphere is cozy and the menu changes often (daily in some cases), so we're never bored. Grab some tasty bites like white bean crostini and crispy thin pizza on Black Wednesday and partake of unlimited drinks from 9 a.m. to midnight for $40. There will also be a live DJ from 9 p.m. to close.
Bar Umbriago, 6 West Hubbard Street (at State Street); 312-494-1200.
Heads up: This new speakeasy of sorts follows the no T-shirts, gym shoes, or sandals policy — so dress to impress. The evening starts with a complimentary whiskey tasting at 7 p.m., followed by a live performance by the Hot Rod Hucksters from 8 to 11 p.m. DJ Greg Corner will play up until the 1 a.m. closing time for those sporting their dancing shoes. That's an awfully long time to drink and not eat, so be sure to snag some of the small plates such as the pork belly confit, pan seared gulf shrimp, or caramel-bacon popcorn. After all, you've got a whole day ahead of you on Thursday.
Untitled, 111 West Kinzie Street (at Clark Street); 312-880-150
It's all about exclusivity at Trencherman. Head to the bar at this popular resto this Wednesday and you'll get to taste its very special barrel-aged Malört neat as part of a Malört flight. You can also sip this potent spirit in one of the specialty cocktails for the evening such as the Laughing Gas: Malört, house-made tonic, and CO2 — not that you'll need an elixir to get in a good mood. If you get there early enough, you can be one of 25 lucky patrons of the evening to taste the "off-the-menu" burger, which changes flavors on a regular basis.
Trencherman, 2039 West North Avenue (at Hoyne Ave); 773-661-1540.
Snag some half-priced tapas like mussels with white wine, crispy patatas bravas, and pork empanadas from 5 to 7 p.m., and wash it all down with $3 glasses (or $15 pitchers) of sangria. If you saunter in a bit later, a DJ will be spinning from 10 p.m. to 2 a.m. There will also be $3 shots of Jameson if it turns out to be that kind of night.
People Tapas Lounge, 1560 North Milwaukee Avenue (between Damen and North Avenue); 773-227-9339.
Tavern On Rush
The lively bar at Tavern always feels as though there's some sort of party going on, so the only difference on Wednesday will be that you can score a beautiful glass of vino for just $8 — a bargain compared to some of its higher priced vintages at this Gold Coast see-and-be-seen spot.
Tavern On Rush, 1031 North Rush Street (between Bellevue Place and Cedar Street); 312-664-9600.
Thanks to ongoing killer entertainment like Calvin Harris, this hot River North respite doesn't need an excuse like Black Wednesday to draw a crowd — you'd probably be going to check out DJ Rick Rude anyway. Be sure to reserve that table reso if you want to have the best seats in the house.
Studio Paris, 59 West Hubbard Street (between Clark and Dearborn Streets); 312-595-0800.
Attention ladies: Wear black to this soirée, and you'll get complimentary bubbly. We don't know about you, but that's half our wardrobe — easy, peasy. There will also be mini-spa services (hello, necessary polish change!), shopping, and drink specials. Sounds like a recipe for a great girls night out.
The Joynt, 650 North Dearborn Street (at Erie Street); 312-573-2233.