30 bars, restaurants, clubs, and venues open after 5. Hours, phone numbers, and vibes included.
Andy's Jazz Club in River North, Chicago, offers an intimate, speakeasy-style setting where live jazz performances mingle with a menu of Southern and Creole-inspired cuisine. A must-visit for music lovers, it blends vintage charm with modern flair, making it a standout destination for Chicago's vibrant nightlife scene.
Upscale cocktail lounge tucked inside the Waldorf Astoria on Walton Street. Bernard's channels old-money sophistication with plush seating, expert bartenders, and a clubby atmosphere that makes you feel like you should be wearing a blazer. Late-night weekends bring a livelier energy without losing the polish.
River North's Blue Chicago has been laying down authentic Chicago Blues since 1985 with high-energy performances every single night. The room runs warm and loud — this is the real thing, not a tourist trap.
Vintage speakeasy in the South Loop that pairs Prohibition-era cocktails with karaoke nights, creating the rare combination of craft drinks and unhinged fun. Brando's nails the speakeasy aesthetic without taking itself too seriously.
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.
Pre-Prohibition cocktail lounge inside The Drake Hotel that has been serving classic drinks since 1933. Coq d'Or is old-school Chicago at its finest -- dark wood, leather booths, and bartenders who know their craft. One of the few bars in the city that genuinely feels unchanged by time.
Craft beer hub and gastropub in the South Loop with an impressive rotating tap list that showcases local and regional breweries. First Draft is the neighborhood's go-to for beer geeks and casual drinkers alike, with solid food to match.
High-energy Gold Coast lounge with live DJs and bottle service on Division Street. The kind of place that draws a well-dressed crowd ready to go late into the night with a proper sound system and VIP sections that deliver.
Modern neighborhood cafe and bar in the South Loop with creative cocktails that punch above their weight. Half Sour bridges the gap between daytime coffee spot and evening cocktail destination, with a relaxed vibe that makes it an easy go-to any day of the week.
River North's year-round rooftop keeps the party going with heated igloos in winter and expansive open-air space in summer. IO Godfrey's craft cocktails and skyline views make it a go-to for after-work drinks and weekend celebrations alike.
Parked right on the Chicago Riverwalk in the Loop, Island Party Hut serves up bottomless mimosa brunches and tropical energy in the heart of downtown. When the weather cooperates, there's no better spot to day-drink on the river.
Chicago's second-oldest continuously operating tavern, holding it down in the South Loop since 1890. Kasey's is the neighborhood bar that survived Prohibition, two World Wars, and every trend. Come for the great beer selection and stay for the no-nonsense atmosphere.
LondonHouse's tri-level rooftop overlooking the Chicago River and Michigan Avenue is one of the city's most photographed cocktail spots. The views from this Magnificent Mile perch are legitimately iconic, and the drinks rise to the occasion.
Mother Hubbard's Sports Pub has been a River North institution since 1993, packed with 45+ TVs and 28 satellite feeds so you can catch any game from any seat in the house. Famous for their legendary Pterodactyl Wings and voted a top restaurant by Restaurant Guru four years running, this is the spot for serious sports fans and late-night revelers alike. Open as late as 5am on Saturdays with pool tables and private party space, Mother Hubbard's delivers an unbeatable game-day atmosphere in the heart of downtown Chicago.
Offshore holds the record as the world's largest rooftop deck, sitting atop Navy Pier with panoramic views of Lake Michigan and the skyline. On a clear night, there's no better perch in the city for a drink.
# 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.
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.
# 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.
Streeter's Tavern bills itself as 'The Greatest Bar Below Earth' — an underground tavern tucked beneath the streets of Streeterville that delivers a one-of-a-kind late-night atmosphere. Every Thursday night features a live DJ from 8 PM to 2 AM, with daily specials running Sunday through Thursday and happy hour Monday through Friday from 5 PM to 7 PM. Part of a well-known family of Chicago bars that includes Lodge Tavern, Redhead Piano Bar, and Original Mother's, Streeter's combines neighborhood charm with downtown energy. Private party bookings are available for groups looking to take over this unique underground space.
Test Venue in Chicago’s Loop is a sleek, intimate bar renowned for its curated cocktail program and immersive, speakeasy-style ambiance. Its exclusive access to rare spirits and bespoke mixology experiences make it a must-visit for discerning nightlife enthusiasts.
Hidden below the Hampton Social in River North, you enter through a secret door and black curtain into a 1960s British-inspired lounge dripping with gold accents, brick walls, and velvet couches. The stage hosts everything from country to soul — it's swanky, loud, and impossible to find unless you know.
Features a rooftop bar with stunning views of the city skyline.
# The Drifter 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 historic tavern with a cozy atmosphere and classic cocktails.