239 bars, restaurants, clubs, and venues open after 5. Hours, phone numbers, and vibes included.
Tucked into Evanston's Custer Street corridor, Oskar is an intimate whiskey bar with a curated brown-spirits menu and daily happy hour. Open until midnight on weekends, it's the kind of low-key hideaway that rewards those who know where to look.
Interactive music experience with four pianists rotating sets, audience requests, sing-alongs, and showmanship. 21+ (18-20 with parent). Open Wed-Sat 7pm-2am. Table reservations recommended for groups.
Neighborhood hideaway bar on the Lincoln Square/Ravenswood border. Classic homemade pub food, tavern wings, billiards. Relaxed, quiet, friendly, unhurried.
Neighborhood sports pub on the Ravenswood/Lincoln Square east border. Full late-night kitchen, thin-crust pizza, local drafts. Casual, lively, approachable.
# Pops for Champagne Since 1982, this River North institution has been the gold standard for bubbles in Chicago—stock up on over 100 sparkling wines at the bar upstairs, then head down to catch live jazz while sipping craft cocktails until midnight on weekends. It's where locals celebrate wins and tourists finally understand why we're obsessed with this place. Dress sharp and arrive early if you want a seat during the weekend jazz sets.
Neighborhood bar with pool tables, darts, pinball, and a solid beer selection. Unpretentious dive that stays open late. The kind of place where you end up staying way longer than planned.
Discover Privé at Provaré, one of Chicago's best hidden speakeasy cocktail lounges, nestled in the basement of Provaré in West Town. This sleek, low-profile 21+ venue delivers an intimate and sexy setting with curated cocktails and Provaré's house favorites — reservations are limited to just 4 guests via Tock. Love Jones Thursdays bring DJ Kid Clay spinning classic R&B remixes and the latest hits, with food service until 9:30 PM Thursdays and 11 PM on weekends. Open Thursday 7 PM–Midnight and Friday–Saturday 6 PM–Midnight, Privé is the perfect secret spot for a sophisticated night out.
Auburn Gresham's neighborhood pub keeps it real with live music, strong pours, and a vibe that welcomes regulars and newcomers alike. Pub 78 is the kind of South Side spot where local talent takes the stage and the crowd actually listens.
This sultry basement cocktail bar beneath Thalia Hall specializes in inventive punch bowls and craft cocktails in a retro-bohemian Pilsen setting. The subterranean vibe on 18th Street is moody, intimate, and built for a night that goes long.
Craft cocktails meet curated playlists in a gorgeously decorated space that feels like a vintage ocean liner. Queen Mary is where Division Street gets classy — expert bartenders, inventive drinks, and an aesthetic that makes every visit feel like an occasion. Date night approved.
Redhead Piano Bar is Chicago's most iconic piano bar in the heart of River North, delivering unforgettable nights with live music seven nights a week. Enjoy vibrant happy hours Sunday through Thursday from 7 to 9pm, and electrifying Ladies Night every Tuesday until 3:30am. Whether you're sipping cocktails or soaking in world-class cabaret and piano performances, Redhead is a must-visit destination for an elevated night out in Chicago.
Arcade sports bar in the heart of Andersonville with classic games, house-made comfort food, and rotating craft beer. Creative seasonal cocktails and late-night hours until 2am on weekends keep the neighborhood coming back.
# Replay Lakeview Boystown's best-kept secret is this free-play arcade bar where you're nursing a perfectly crafted cocktail while crushing it at vintage Pac-Man and pinball machines until 3 AM on Saturday nights. The themed drinks hit as hard as the nostalgia, and the welcoming LGBTQ+ crowd makes it feel like you're gaming with friends who actually get it. Skip the overcrowded dance clubs and post up here instead—it's arcade heaven without pretension.
# Revolution Brewing Taproom Head to Pilsen's Revolution Brewing Taproom if you want to taste Chicago's largest independent craft brewery straight from the source—their rotating taps showcase limited releases you won't find anywhere else. Grab a seat in the sprawling beer hall (open until 10 PM weekends) or book a 45-minute brewery tour to see exactly how they're pushing the boundaries of what local beer can be.
A dive bar known for its cheap drinks and no-frills atmosphere.
Unpretentious corner dive bar in Lincoln Square. Darts, craft beer, and a relaxed local crowd. Outside food delivery welcomed from surrounding pizzerias. Nostalgic, competitive, friendly.
Downtown Evanston tavern keeping the kitchen running late with craft cocktails, shareable plates, and a menu that goes beyond typical bar food. Open until midnight weekdays and 1 AM on weekends, Ridgeville is one of the north shore's best after-dark options.
Dog-friendly craft cocktail and beer bar in Rogers Park's Glenwood Ave arts district, open until 3am on Saturdays. The solid happy hour and laid-back neighborhood energy make it the far North Side's go-to after-dark spot.
# ROOF on theWit Perched 27 stories above downtown Chicago, this Loop rooftop commands views that'll make you forget you're in the Midwest—think cool, coastal energy with skyline drama. The craft cocktail program is legit, DJ sets keep the vibe electric, and they're slinging quality pizza and sushi while you're sipping. It's consistently ranked in the global top 3 for rooftop bars, and if you're looking to see the city from above without the tourist trap feel, this is the move.
Room 13 is a authentic speakeasy lounge in Lakeview.
Humboldt Park's essential natural wine and craft beer bar pairs a standout bottle list with seasonal small plates that are just as compelling. It's the neighborhood's best date-night anchor, tucked into a cozy room on California Avenue.
Sakura Karaoke Bar in Chinatown delivers authentic late-night karaoke with 80,000+ songs across Chinese, Japanese, Korean, and English in private rooms perfect for groups. Steps from the Red Line, it's where locals belt out hits until dawn in one of the city's most vibrant neighborhoods.
With a near-perfect 4.9 rating, this Humboldt Park sports bar delivers good vibes, quick service, and prices that won't break the bank. Sari's flies under the radar on the west end of Division Street, but the locals who know it swear by it. Unpretentious, welcoming, and exactly what a neighborhood bar should be.
Logan Square's definitive gin bar backs an inventive cocktail program with a lush backyard patio and a late-night menu that draws the neighborhood's creative crowd. The gin collection here is arguably the deepest in the city.