Spiked milkshake and burger at 25 Degrees
440 N. State St. 312-464-1400
At the neighborhood’s only gay bar, expect the bartenders to call you “honey” and the entertainment to range from live cabaret to karaoke to DJs.
The Purple Pig
500 N. Michigan Ave. 312-464-1744
This small but mighty wine and swine bar is packed every night of the week with diners hungry for a taste of charcuterie, cheese and treats that do the name proud, from pork neck bone rillettes to pig’s tails braised in balsamic vinegar.
325 W. Huron St. 312-664-2727
This Pan-Latin restaurant is well-loved for its globe-trotting menu and innovative cocktails designed by mixologist Adam Seger. Latin dancing nights make for prime people-watching.
GT Fish & Oyster
531 N. Wells St. 312-929-3501
This nautical-chic seafood restaurant with chef Giuseppe Tentori (Boka) in the kitchen serves classics such as oyster platters, clam chowder and lobster rolls, along with contemporary plates such as hamachi crudo with strawberry and shiso.
59 W. Grand Ave. 312-645-9500
This always-bustling dining room serves up a massive menu of traditional Indian dishes, including specialty dishes baked in a tandoor oven.
339 N. Dearborn St. 312-755-9463
This wine bar/restaurant/store hybrid headed up by wine director Brian Duncan quite possibly the best place in the ’hood to further your grape know-how.
626 N. State St. 312-698-5000
This bustling Italian small-plates spot with excellent pizza is a perpetual pleaser of dates, parents and everyone in between.
41 E. Superior St. 312-266-0400
This sporty pub has learned a following for its hefty selection of wings (spice ratings range from traditional buffalo to XXX) along with a solid craft beer list.
155 W Kinzie St. 312-245-2000
Garage doors that open up onto the street and a mezzanine level that overlooks the main dining room make this lively cantina a popular pick for post-work sangria and Latin-inspired snacks.
Dragon Ranch Moonshine & BBQ
441 N. Clark St. 312-955-1900
All-American flavors mix with a hint of Far Eastern influence at this eatery, which serves dishes such as slow-smoked pulled pork rubbed with a blend of Asian spices alongside moonshine cocktails served in Mason jars.
401 N. Wabash Ave. 312-588-8030
This restaurant has the formal service, luxe look and decadent dishes you’d expect of its location on the 16th floor of the Trump International Hotel & Tower—with prices to match. The dining room features sweeping views of the Wrigley Building, Tribune Tower and the Chicago River, as does hotel lounge Rebar on the tower’s second floor.
15 E. Huron St. 312-587-1000
The Ikram cafe, located on the second level of the uber-ubscape women's boutique of the same name, serves a frequently changing menu of salads, sandwiches and other lunchy items, all inspired by what’s fresh at the farmers market.
Blue Frog Bar & Grill
676 N. La Salle Drive 312-943-8900
No-cover karaoke hosted is nearly every night of the week at this kitschy dive bar, which is cheekily decorated with holiday lights and classic board games and toys from the ’70s and ’80s.
5 W. Ontario St. 312-428-3548
Tasty toppings such as crispy bacon and snappy pickles belie the fast-food prices at this burger joint. This location serves chocolate-dipped ice cream cones in addition to milkshakes and malts (ask for the featured flavor).
736 N. Clark St. 312-943-9700
Spiked milkshakes and build-your-own burgers are the main attraction at this bar, which rocks a sultry parlor-like look with vintage-inspired wallpaper and chandeliers.
5 W. Hubbard St. 312-828-0007
Locals and tourists constantly fill this sports bar staple, known for its ample TVs, draft beers and saucy buffalo wings.
400 N. State St. 312-265-1240
This perpetually packed corner bar brings the party to your booth thanks to beer and liquor taps built right into the table; the same technology was first introduced at sibling bar Bull & Bear on the west side of River North.
Stout Barrel House & Galley
642 N. Clark St. 312-475-1390
It would be easy to mistake Stout for just another hangout working the “upscale tavern” model, but a late-night bar license and to-go sliders served until 3 a.m. set it apart from the pack.
412 N. State St. 312-644-5775
This reliable cash-only dive/packaged goods store is one of the only bars of its kind left in the neighborhood. While it’s usually crowded with regulars on weeknights, Friday nights bring a rush of nearby office workers grabbing a cheap beer before heading home.
111 W. Kinzie St. 312-880-1511
To find this so-called “speakeasy” inspired by supper clubs of times past, look for the unmarked, glossy black doors (and a valet stand) near the CVS. Inside, you’ll find a massive multi-room restaurant and bar serving indulgent small plates and craft cocktails.
52 W. Illinois St. 312-222-1888
Chicago’s own reality TV couple, Bill and Giuliana Rancic, teamed up with Lettuce Entertain You's Melman siblings (RJ, Jerrod and Molly Melman of Hub 51 and Paris Club) to open this glitzy restaurant and bar serving Italian dishes meant for sharing.