Bars, restaurants, clubs, and venues open after 5. Hours, phone numbers, and vibes included.
Theater in Wrigleyville at 1910 West Irving Park Road.
High-energy, sleek South Loop destination popular with Black professionals. Features a heavy Sunday evening DJ rotation spinning 90s hip-hop, timeless R&B, and neo-soul alongside upscale cocktails and wings.
A beloved Logan Square live music bar and arts venue since 2010, The Burlington is one of Chicago most respected independent stages. Hosting local and touring acts nightly across rock, indie, folk, and experimental genres, the bar has earned a reputation as the heartbeat of Chicago neighborhood music scene.
Music venue in South Loop at 1559 S Lakeshore drive.
Iconic lakefront park in Hyde Park with stunning Chicago skyline views. Known for cookouts, community gatherings, and sunset watching. The limestone ledge is a South Side landmark.
Comedy club in Old Town at 1447 North Wells Street.
This upscale Lincoln Park steakhouse serves a legendary carnivorous tasting menu featuring an exclusive steak flight. Beyond the famous steak flights, diners indulge in perfectly seared prime cuts, decadent sides, and craft cocktails. The ambiance is moody, contemporary, and romantically cozy — an excellent choice for date night or a business dinner.
Legendary Irish tavern and Gold Coast institution on Division Street since 1961. The quirky, eccentric decor changes with the seasons, the drinks are strong, and the crowd is a mix of regulars and first-timers who all end up having the same great time.
Bar in Wrigleyville at 3707 North Halsted Street.
An iconic Chicago concert hall with a storied history dating back to 1926. The Byline Bank Aragon Ballroom in Uptown seats up to 5,000 for major national touring acts, and its Spanish Baroque interior — ornate archways, painted murals, and a distinctive cloud-effect ceiling — makes every show a visual experience. Located one block from the Lawrence L stop.
A neighborhood sports bar and grill on Halsted Street in West Pullman, serving the far South Side community with drinks, food, and game watching.
Nightclub in West Loop at 200 North Green Street.
James Beard winner Stephanie Izard's rooftop retreat atop the Hoxton Hotel in Fulton Market serves bold Peruvian-inspired plates with skyline views that don't quit. Cabra is the kind of place where the ceviche, the cocktails, and the sunset all compete for your attention.
The Loop's Cadillac Palace Theatre hosts major Broadway touring productions in a stunningly restored Vaudeville-era setting. The gilded interior is as much a show as whatever's on stage — this is how theater was meant to be experienced.
Logan Square daytime cafe, nighttime bar, and celebrated music venue since 2010. Voted Chicago Best Non-Traditional Music Venue by the Chicago Reader. Serving craft cocktails, local coffee, and a night snack menu, Cafe Mustache hosts live music and karaoke nightly — Fridays at 10pm, Saturdays and Sundays at 8pm. A true neighborhood institution with an anything-goes creative spirit.
South Side Cajun seafood boil with crab legs, crawfish, and shrimp. Choose your spice level and sauce. Casual counter service, big portions, cold beer available.
Iconic smoked fish shack on the far South East Side. Cash only, standing room only. James Beard Award winner. A Chicago original since 1948.
Gritty, deep-neighborhood late-night dive bar filled with old school jukebox lines and cheap, heavy pours. Street-style Steak Tacos, Tamales, Chicharrones, Draft Beer Cervezas.
Canal Street Eatery in the West Loop offers unlimited pizza, pasta, and salad for those who believe more is more. A solid group-dinner option near the Fulton Market corridor when everyone's hungry and nobody wants to overthink it.
Northwest Side regulars know Cannabist near Jefferson Park Blue Line as the former Columbia Care, now serving both medical and rec crowds in Portage Park’s leafy stretch. Rebranded but still rooted in the neighborhood’s cannabis scene, it’s a quiet hub where locals grab products without the tourist crowds.
Virtue Hospitality's Hyde Park gem serves seriously crafted agave cocktails and small-bite botanas in a space that actually feels like a proper escape—not some Instagram fever dream. Skip the Loop lounges and grab a date-night cocktail here where the bartenders know their mezcal from their tequila. The tropical drinks hit different when you're tucked into this corner of the South Side.
Deeply authentic, brick-walled Mexican steakhouse centered around open-fire grilling and social dining. Charbroiled Arrachera Skirt Steak, Grilled Onions, Fresh Guacamole, Charro Beans.
Lively Mexican restaurant and taco bar in Bridgeport known for Taco Tuesday specials ($2.50 select tacos), $7 margaritas, and $5 shots. A festive neighborhood spot for casual Mexican food and cocktails.