Big Star in Chicago is the One Off Hospitality taco room at Six Corners on Damen, with an outdoor patio, a frozen margarita machine and tacos al pastor.
OrderThree al pastor tacos, a frozen margarita, chips with the smoky tomato salsa.
TipThe patio queue is long in summer. The walk-up window pays out a perfectly good takeaway dinner in five minutes.
Chicago Food Planet runs the Bucktown and Wicker Park food tour with six tastings across the neighborhood. The route covers a slice of Chicago-style pizza, a tapas plate, a deep-dish slice and a cocktail finish.
TipTours run Friday through Sunday at 11:00 and 14:00. Vegetarian options on advance request.
Subterranean in Chicago has anchored Wicker Park's six-corners since 1994. Three floors host hip-hop showcases, indie nights and a Wednesday open mic.
TipDoors usually 20:00 with show at 21:00. The balcony has the clearest sight line over the floor; Wednesdays are free open mic on the main stage.
Empty Bottle on North Western has hosted indie, punk and experimental music in Ukrainian Village since 1992 and turned 33 in 2025, with free Monday night residencies that still anchor the calendar.
TipOpen daily 17:00-02:00, Saturday until 03:00. Monday's free residency is the easy walk-in entry to the scene. Pizza Friendly Pizza is next door.
The Hideout in Chicago is the Wabansia Avenue clapboard cottage in the Elston industrial corridor, hosting Americana, experimental and the Robbie Fulks Monday residency.
TipTuesday through Thursday close at midnight, Friday and Saturday at 01:00. The room holds about 100 and the bands play through the bar conversation.
The Up Room crowns the 13th floor of The Robey, Wicker Park's tallest building, with a wraparound terrace facing the Loop skyline and the six-corners street.
TipOpen daily from 17:00, weekends until 01:00. Sunset window books fast; weeknights walk in easy and the inside lounge stays open in winter.
The Violet Hour in Chicago hides behind a rotating mural on Damen Avenue. The James Beard winning pre-Prohibition room opened 2007 with curtained salons and a marble bar.
TipNo reservations, walk in. The line out front moves; once you are inside the rule is no cell phones and conversations stay below the music.
Dorian's in Chicago hides behind a small Wicker Park record shop. The listening booth doubles as the waiting room before the bar and stage open behind a back curtain.
TipWalk through the storefront record shop; the bar runs behind it. Live jazz most nights, Italian-made hi-fi sound system, no cover before 22:00.
Innertown Pub on West Thomas has poured cheap beer in Ukrainian Village since 1983 with free pool, darts, a Tom Waits jukebox and a back room of taxidermy and rummage art.
TipCash preferred, kitchen-free. Open to 02:00 weeknights, 03:00 Saturday. The crowd shows up after 22:00 and the booths fill last.
Guided tour · 3 hours
Taste the finest examples of Artisan, Neapolitan, Detroit Style, and Chicago deep-dish pizza on this professionally guided walking tour that takes you to highly-rated ...
Water activity · 2h 30m
An unforgettable celebration of holiday cheer and fine dining awaits on our Christmas Eve Dinner Cruise on Lake Michigan. Enjoy a 3-course plated dinner, an on board D...
2 hours
Make pasta night feel like a full Italian escape in this fun 4-course cooking class in Chicago. Learn to roll ravioli from scratch, prepare a vodka sauce and a veggie ...