Bars, restaurants, clubs, and venues open after 5. Hours, phone numbers, and vibes included.
60+ craft beers on tap in Orland Park with gourmet sliders, tacos, and giant pretzels. Kitchen stays open till midnight on weekends — a serious beer bar in the south burbs.
Seeking a spot where Pilsen’s laid-back energy meets impeccable craft beer? The Bungalow delivers a relaxed vibe and a stellar selection, perfect for unwinding with locals who know the neighborhood inside out. No pretense, just great pours and easy conversation.
Humboldt Park’s original speakeasy, The California Clipper has been pouring vintage cocktails and hosting live jazz since ’37—its mahogany booths and 3am Saturday curfew make it a time capsule for locals who know where to look. Seasonal drinks and a tavern soul that’s survived decades of Chicago nights keep the crowd loyal.
Bar in Naperville at 634 East Ogden Avenue.
The Charleston’s weathered charm and ornate tin ceiling make it a Bucktown staple, where craft beers flow late into the night. Open until 2am weeknights and 3am Saturdays, it’s a no-frills hangout for locals who know the west side’s best-kept secrets.
Combines magic shows with a bar experience in a vintage setting.
A classic dive bar known for its laid-back vibe and cheap drinks.
Chicago's oldest LGBTQ+ bar catering to women, The Closet has been a Lakeview staple for over 50 years. A neighborhood dive with a loyal sapphic following — karaoke nights, video bowling, darts, and a no-frills vibe that keeps people coming back. Open until 4am nightly, it's a beloved late-night anchor of Boystown.
The Comedy Bar in Chicago is an iconic venue renowned for its electrifying stand-up comedy nights, featuring both established and emerging talent in an intimate, upscale setting. Its lively ambiance and elite crowd make it a worth visiting destination for those seeking the pinnacle of Chicago’s comedy scene.
Features a rooftop bar with stunning views of the city skyline.
Dive deep into Hyde Park's most unpretentious watering hole, where University of Chicago students and grizzled regulars stake claims on worn bar stools and nursing cheap whiskeys that actually taste good. Pool games, zero pretense, and the kind of neighborhood authenticity that money can't buy—just don't expect craft cocktails or Instagram moments here.
Slip through the Green Door Tavern's hidden bookshelf in River North and you'll find yourself in a legit Prohibition-era speakeasy where the bartenders pull your daily cocktail menu based on a tarot reading. The velvet booths, dim lighting, and carefully crafted cocktails keep the vibe intimate and theatrical until 2 AM—this is the kind of spot where locals go to actually disappear.
A gastropub with a cozy atmosphere and a focus on seasonal ingredients.
Bronzeville's most eccentric spot has been mixing craft cocktails with cosmetics since 1999—grab a drink at the bar, browse vintage beauty products, and catch live performances in the same room. The Miami-inspired aesthetic and elevated tacos make this a rare breed of venue that actually delivers on its quirky premise. It's the kind of place where you'll see someone buying lipstick between sets, and that's exactly why locals keep coming back.
Legendary indie rock dive bar in Ukrainian Village, known for its raw, authentic live music crowd. One of Chicago's most respected independent music venues for over two decades.
Black-owned cocktail lounge south of the city specializing in handcrafted cocktails, rare bourbons, and curated wines in a sleek, intimate setting. The Exclusive Pour is built for date nights with a sophisticated after-five energy that sets the standard.
High-octane, vehicle-themed bar with a packed outdoor roof deck blasted with sunlight and heavy music. Pulled pork sliders, smoked wings, craft beer taps, and signature bourbons.
Secret bar above the Bourgeois Pig coffee shop. Password required. Prohibition-era metal door leads to fancy cocktails and a transformed neighborhood speakeasy.
Stylish cocktail bar on the Lincoln Square-Ravenswood border pouring craft cocktails with a relaxed neighborhood feel. Happy hour starts at 3pm on weekends, and the bar stays open until 3am on Saturdays for the night owls.
Wrigleyville sports bar steps from Wrigley Field, known for themed events, creative drink specials, and a crowd that brings the energy whether or not there's a game. The Graystone is a pre-game ritual and a post-game destination in its own right.
A historic tavern with a cozy atmosphere and classic cocktails.
Swinging, high-energy 1940s-style jazz lounge with legendary late-night jam sessions, heavy drink pours, and rich Chicago history. Once a Prohibition-era speakeasy frequented by Al Capone.
Pilsen's go-to post-concert spot sits right across from Thalia Hall with affordable craft cocktails and a chill vibe that keeps the night going until 3am on Saturdays. It's the perfect second stop after a show on 18th Street.