Bars, restaurants, clubs, and venues open after 5. Hours, phone numbers, and vibes included.
Billy Sunday is a vintage amaro cocktail bar in Logan Square, serving Chicago's north side.
Tucked into Lincoln Square with a beautiful garden patio and classic Provencal dishes, Bistro Campagne is one of the best date-night restaurants on the North Side. The wine list is deep, the atmosphere is charming, and the French cooking is the real deal.
An acclaimed professional theater company dedicated to producing plays, musicals, and performances celebrating African American culture and history. Founded by Jackie Taylor, it presents world-class productions featuring blues, jazz, and theatrical performances on Chicago\x27s North Side.
Blazed Bakery Chicago is a cannabis-infused cafe in Logan Square, serving Chicago's north side.
Boka's Lincoln Park location serves as the gold standard for Chicago date nights, with Chef Lee Wolen's seasonal American tasting menus delivered in an intimate, garden-enclosed dining room that feels like a secret. This Michelin-starred kitchen doesn't play it safe—expect precise technique and unexpected flavor combinations that justify the price tag and the reservation battle.
Behind a hidden grass door on Division Street in Wicker Park lies Bordel, a Parisian-inspired speakeasy lit entirely by candlelight. Nightly jazz, burlesque, and live entertainment share the room with savory small plates — it's moody, romantic, and very hard to leave.
This energetic spot on Clark Street doubles as a lively neighborhood community lounge serving classic Cameroonian and Central African street food staples, including seasoned grilled brochettes and roasted fish. Open late into the night with weekend music mixes, soccer match watch parties, and smooth lounge vibes — a fantastic social hotspot to share a drink and enjoy deep, savory finger foods into the early morning.
Andersonville newest gem for arts and culture. The Bramble Arts Loft occupies the second floor of the historic Capital Garage building on Clark Street, featuring The Beatrice (101-seat thrust theater), The Berry (900+ sq ft black box), and The Cabaret, a cozy intimate performance space. Home to Bramble Theatre Company, a 501(c)(3) nonprofit — 100% of venue profits support equitable arts access across Chicago.
A destination for lively drinks and convivial dining on the third floor of the legendary Waldorf Astoria Chicago. Brass Tack serves French-American cuisine with a modern twist — shareable plates, craft cocktails, and an expertly curated wine list — in a laid-back yet upscale Gold Coast setting. With a renowned bar area, private dining options, and stunning Gold Coast views, it is the quintessential Chicago date night spot.
A top mid-size Broadway venue in the heart of the Magnificent Mile, housed in the northeast corner of Water Tower Place. Originally built in the 1970s as The Drury Lane Theatre, the Broadway Playhouse at Water Tower Place is part of the Broadway In Chicago family and hosts touring productions in an intimate 590-seat setting — just steps from Michigan Avenue.
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.
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.
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.
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.
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.
Upscale, sophisticated lounge with a bustling late-night downtown bar scene. Baby back ribs, prime rib eye, Texas brisket, and bourbon cocktails.
Casa Tequila Chicago is a tex-mex steakhouse in Wicker Park, serving Chicago's north side.
Synonymous with summertime in Chicago, Castaways Beach Club is the iconic boathouse on North Avenue Beach with the best skyline views in the city. This reimagined summer destination blends classic lakefront charm with modern design — serving elevated food, craft cocktails, and hosting rooftop house music sets and high-energy summer parties on the North Deck from May through September.
Tucked away in Chicago's Gold Coast, this preserved 1904 mansion offers a rare glimpse into early 20th-century design through curated architecture lectures and exclusive behind-the-scenes tours. Its quiet, upscale atmosphere makes it a favorite for culture-focused visitors seeking a refined, low-key experience.
Straight-up Sichuan cooking that doesn't pull punches -- the mapo tofu and mouth-numbing boiled fish are why people trek across Chicago for this place. Multiple locations across the city, each holding the line on bold, regional Chengdu flavors.
Chicagos top architecture education and cultural institution, located along the Chicago River in the Loop. The Chicago Architecture Center features rotating exhibitions, boat tours, walking tours, and programming celebrating the city world-famous built environment. A top destination for curious adults and design enthusiasts, with stunning river views and the nations largest model of downtown Chicago.
Comedy Bar Chicago (Chicago Comedy Lounge) brings the acclaimed Comedy Bar brand to the Lincoln Park neighborhood. Featuring nightly stand-up, improv, and sketch comedy shows in a full bar setting, it is a top for comedy fans on the North Side. Intimate theater seating ensures every angle is a great view.
A stunning Beaux-Arts landmark in the Loop and one of Chicagos most beloved free cultural venues. The Chicago Cultural Center hosts world-class art exhibitions, live music, film screenings, lectures, and public programs year-round. Its intricate Tiffany glass dome and Preston Bradley Hall are among the most spectacular interior spaces in the city.
Riverfront steakhouse with jaw-dropping Chicago River views, an in-house dry-aging program, and bone-in filets that justify every dollar. Chicago Cut is where you take someone when the view and the steak both need to be unforgettable.