71 bars, restaurants, clubs, and venues open after 5. Hours, phone numbers, and vibes included.
Upscale Italian by Lettuce Entertain You. House-made pastas, prime steaks, and an extensive Italian wine list in a sleek River North setting.
# Saltwater Coastal Grill Nestled inside Parkway Bank Park, this upscale seafood spot delivers legit East Coast oysters and pristine sushi alongside wood-fired entrées that actually justify the price tag. The polished dining room makes it the move for a serious date night without the stuffiness—you're getting quality Mediterranean-fusion cooking in a ballpark setting that somehow works. Hit it before or after catching a Raptors game if you're already in the neighborhood.
Schwa is a michelin-starred avant-garde in Wicker Park, serving Chicago's north side.
SeatGeek Stadium in Chicago is a premier multi-purpose venue renowned for hosting electrifying concerts, major sports events, and high-profile gatherings under its state-of-the-art, climate-controlled dome. Its upscale ambiance, cutting-edge technology, and prime location make it a must-visit destination for discerning nightlife enthusiasts seeking unforgettable experiences.
Chicago's iconic upscale seafood destination since 1984. Raw bar, king crab legs, oysters, and jazz in the Oyster Bar. The main dining room is white-tablecloth; the bar side is lively and fun. Late night oyster happy hour.
# Sifr Sifr's open-fire cooking and rooftop perch make it the rare spot where serious Middle Eastern cuisine meets proper Chicago nightlife vibes. The bold, shareable mezze lineup hits different when you're trading bites with a crew under the city lights, and their Michelin Bib Gourmand nod proves this isn't just Instagram bait. It's where you go when you want to eat exceptionally well and actually stay out.
Sofitel's Gold Coast location hosts an upscale afternoon apero that elevates the concept of after-work drinks to something genuinely French and refined. The lobby bar's sleek design and curated cocktail menu make it a Magnificent Mile standout for those who prefer sophistication over volume.
4.7 stars, 133 reviews. $100+. Friendly staff and great music selection. Upscale bottle service nightclub.
Michelin-starred chef Jenner Tomaska's luxurious third-floor steakhouse blends Midwestern prime beef with 1920s French Nouvelle elegance. The Alston operates with a private members club sensibility that makes every dinner feel like an invitation-only affair.
Upscale dining in a stunning, meticulously restored 1905 firehouse on Michigan Avenue. The Chicago Firehouse Restaurant serves classic American fare with style in one of the South Loop's most architecturally impressive spaces. The original fire poles are still there -- the lobster bisque is legendary.
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 vibrant ambiance and elite crowd make it a must-visit destination for those seeking the pinnacle of Chicago’s comedy scene.
Upscale American tavern in the Loops historic landmark building. Seasonal cocktails, raw bar, and elevated comfort food. Popular for pre-theater dining.
The Gage is a Michelin Guide Recommended gastropub on Michigan Avenue, housed in historically landmarked buildings from the 1800s in Chicago's Loop. Savor refined, rustic fare and award-winning cocktails in a space celebrated with OpenTable's Top 100 Restaurants in America and a Wine Spectator Award of Excellence. With happy hour Monday through Thursday from 2 to 5pm and kitchen hours extending to midnight on weekends, The Gage is a perfect destination for after-work drinks, date nights, and pre-theater dining.
Coastal-inspired dining at Old Orchard. Rosé all day, fresh seafood, and a flower wall for Instagram. Upscale, social, lively.
The Signature Room, located on the 23rd floor of the Trump International Hotel in Chicago, offers panoramic views of the city skyline and the Chicago River, creating an iconic backdrop for upscale dining. Its sophisticated ambiance, paired with a curated menu and a lively bar scene, makes it a premier destination for both fine dining and vibrant nightlife in the Loop.
First and only upscale dine-in restaurant in North Lawndale. Elegant atmosphere for date nights. Founded by Chicago native Chef Quentin Love. Closed Mon-Tue.
River North's Three Cities Social Club is a stylish venue hosting professional networking events, summits, and upscale social gatherings. The crowd skews ambitious and well-dressed — bring business cards.
Tzuco is a michelin french-mexican fusion in River North, serving Chicago's downtown side.
Tinley Park's modern bar-and-grill concept pairs an upscale-casual menu with craft cocktails and a polished sports-bar atmosphere. Union Bar & Grill keeps late hours Thursday through Saturday for the after-work and weekend crowd in the south suburbs.
Chic rooftop lounge atop The Robey Hotel with panoramic views of the Bucktown/Wicker Park skyline. Upscale small plates, artisanal cocktails, and weekend DJ sets. Sophisticated, scenic, trendy.
Upscale Southern cuisine in Hyde Park. James Beard-recognized. Perfect for date night with elevated cocktails and refined comfort food.
Rooftop lounge in the South Loop with panoramic city views. Hosts Afrobeats day parties, bottle service, and upscale events. Trendy, elite, sophisticated.
Wintrust Arena in Chicago is a sleek, state-of-the-art venue renowned for hosting world-class concerts, sports events, and exclusive galas, offering an immersive experience with cutting-edge technology and premium amenities. Its upscale atmosphere, combined with impeccable service and diverse entertainment options, makes it a top destination for discerning nightlife seekers in the city.