Chicago's February can be brutal—wind that cuts through your bones, temperatures that laugh at your North Face—but this weekend delivers a lineup that'll have you gladly braving the elements. From Grammy-nominated comedy royalty to dubstep dinosaurs, street festivals with a soundtrack, and a national tour stop of a Tony-sweeping musical, there's no excuse to hibernate. Whether you're warming up with bass drops at The Salt Shed, catching a multi-night comedy run at the Chicago Theatre, or celebrating Lunar New Year in Uptown, the city's got something for every kind of cold-weather warrior.
Valentine's Day may be behind us, but the love for live music, great comedy, and world-class performances continues. This weekend brings Indonesian rap sensation Rich Brian, Mexican hip-hop heavyweights, multiple Bulls games at the United Center, and the return of Chicago's frostiest outdoor festival. The Joffrey Ballet pays tribute to legendary choreographers, while the Tony Award-winning The Outsiders continues its run at the Cadillac Palace.
Ready to earn those bragging rights? Browse the full rundown on AllEvents and lock in your weekend plans.
How this list works: We've handpicked the top events happening Friday, February 20 through Sunday, February 22. The lineup spans music, comedy, culture, sports, and performing arts—curated to give you a mix of headliners and hidden gems worth your time (and your CTA fare).
What it is: America's favorite observational comic brings his "Everything is Wonderful!" tour to the Chicago Theatre for a multi-night run. Gaffigan—known for his Hot Pockets bits and signature whispered asides—delivers clean comedy that somehow makes everyday minutiae absolutely hilarious. His self-deprecating humor about parenting, food, and laziness has made him a household name.
Why go: Gaffigan consistently sells out arenas, and there's a reason: his comedy transcends demographics. Whether you're a college student or bringing your parents, everyone leaves quoting his routines. The Chicago Theatre's ornate architecture adds extra magic to the experience, and multiple showtimes mean you can actually snag seats.
Who it's for: Comedy lovers of all ages, families, anyone who's ever had strong feelings about bacon
When: Friday, February 20 & Saturday, February 21, 2026 | 7:00 PM | Chicago Theatre
What it is: Six-time Grammy winner Brandi Carlile brings her emotionally charged folk-rock to Allstate Arena in Rosemont, with fellow Pacific Northwest favorites The Head and The Heart as direct support. Carlile's powerhouse vocals and raw storytelling have made her one of the most respected artists in modern Americana—expect songs from across her catalog including By the Way, I Forgive You and In These Silent Days.
Why go: This pairing is practically a dream double-header for anyone who loves heartfelt songwriting. Carlile's live performances are legendary—she brings an intensity and vulnerability that translates perfectly to arena settings. Add The Head and The Heart's anthemic indie-folk, and you've got a show that'll have the whole venue singing along.
Who it's for: Folk and Americana fans, Lilith Fair devotees, anyone who wants to feel something deeply
When: Friday, February 20, 2026 | 7:00 PM | Allstate Arena, Rosemont
What it is: Indonesian rapper Rich Brian—who broke the internet as a teenager with "Dat $tick" in 2016—brings his "Where Is My Head?" world tour to the Riviera Theatre. Now a seasoned artist signed to 88rising, Rich Brian delivers introspective hip-hop that showcases his growth from viral sensation to legitimate MC. The tour supports his genre-bending new project that blends storytelling with experimental production.
Why go: Rich Brian's journey from Indonesian kid making videos in his bedroom to global hip-hop star is one of the most unlikely success stories in recent music history. His live shows bring energy and authenticity, and the Riv's standing-room setup means you'll be close to the action. This is hip-hop with genuine emotional depth.
Who it's for: Hip-hop heads, 88rising fans, anyone who appreciates an underdog story
When: Friday, February 20, 2026 | 7:30 PM | Riviera Theatre
What it is: Heavyweight dubstep producer Wooli brings his "Synapse Tour" to The Salt Shed, armed with prehistoric soundscapes and earth-shaking bass that's made him a festival headliner. Known for blending melodic dubstep with ridiculously heavy drops, Wooli creates music that's both emotional and absolutely crushing. Expect brand new material alongside his biggest tracks.
Why go: The Salt Shed's industrial-chic indoor space is perfect for electronic shows—the sound system hits different here. Wooli has been teasing new music specifically for this tour, meaning you might catch something nobody else has heard yet. If you like your bass music with actual melodies and dinosaur-themed visuals, this is your show.
Who it's for: EDM enthusiasts, bass music lovers, anyone who wants to feel frequencies in their chest
When: Friday, February 20, 2026 | 8:00 PM | The Salt Shed (Indoors)
What it is: The winner of four 2024 Tony Awards including Best Musical, The Outsiders is the hit stage adaptation of S.E. Hinton's classic coming-of-age novel about Greasers vs. Socs in 1960s Oklahoma. The national tour has landed at the Cadillac Palace Theatre through February 22, bringing its visceral choreography, rock-tinged score, and raw teenage emotion to Chicago audiences.
Why go: This isn't your high school's version of The Outsiders—it's a theatrical knockout that earned those Tony wins. The production captures the novel's heart while delivering genuinely thrilling staging. If you grew up loving the book (or the movie), this reimagining will hit you right in the nostalgia while showing you something completely fresh.
Who it's for: Musical theater fans, anyone who read the book in middle school, teens and their parents
When: Friday 7:30 PM, Saturday 2:00 PM & 8:00 PM, Sunday 2:00 PM | February 20–22, 2026 | Cadillac Palace Theatre
What it is: Uptown's Argyle Street transforms for the annual Lunar New Year Celebration welcoming the Year of the Snake. The free festival features traditional dragon and lion dances, live performances, cultural demonstrations, and food from the neighborhood's legendary Vietnamese and Chinese restaurants. The parade kicks off at 1:00 PM at Argyle and Sheridan.
Why go: Argyle is Chicago's authentic Asian culinary corridor, and this celebration lets you experience the neighborhood at its most vibrant. The parade brings color and energy to otherwise gray February streets, and you can warm up afterwards with pho or bánh mì from spots that locals have loved for decades. It's free, family-friendly, and quintessentially Chicago.
Who it's for: Families, foodies, anyone celebrating Lunar New Year, culture enthusiasts
When: Saturday, February 21, 2026 | 10:30 AM–4:00 PM (Parade at 1:00 PM) | Argyle Street, Uptown
What it is: Mexican hip-hop superstars Aleman and Gera MX bring their "Rich Mafia Tour" to the Aragon Ballroom. Both artists have shaped the Latin trap and hip-hop scene in Mexico, with Aleman's smooth flow and Gera MX's storytelling earning them massive followings on both sides of the border. Together, they're a powerhouse pairing for anyone who follows Spanish-language hip-hop.
Why go: The Aragon Ballroom's ornate interior and massive floor space make it ideal for this kind of high-energy hip-hop show. These two are among the biggest names in Mexican rap right now, and the Chi has a massive fanbase waiting for them. Tickets start at just $22, making this an incredible value for a show of this caliber.
Who it's for: Latin hip-hop fans, Spanish speakers, anyone who appreciates rap en español
When: Saturday, February 21, 2026 | 8:00 PM | Aragon Ballroom
What it is: Dubstep producer Ray Volpe brings his signature "Let's Go" energy to Radius, supported by heavy hitters Samplifire, Tynan, and EDDIE. Known for his melodic yet absolutely punishing bass music, Ray Volpe creates tracks that build emotional tension before absolutely obliterating the drop. His production style bridges the gap between feels and filth.
Why go: Radius is one of Chicago's premier electronic music venues, with a sound system designed specifically for bass-heavy shows. This lineup is stacked—Samplifire and Tynan alone could headline smaller shows—making it an exceptional value. If you're into dubstep that actually makes you feel something before destroying you, this is the ticket.
Who it's for: Dubstep fans, bass music warriors, anyone who wants to go out Saturday night and go hard
When: Saturday, February 21, 2026 | 10:00 PM | Radius (18+)
What it is: Swedish lo-fi house maestro DJ Seinfeld (Armand Jakobsson) brings his nostalgic, VHS-tinged house music to Smartbar. One of the key figures in the lo-fi house movement, DJ Seinfeld creates warm, emotive tracks that feel like rediscovered gems from the '90s—perfect for dancing until the early morning hours.
Why go: Smartbar is a Chicago institution for underground electronic music, and DJ Seinfeld fits the vibe perfectly. His sound is hypnotic and danceable without being overly aggressive—ideal for getting lost in the music until 4 AM. Supporting sets from Madeline and Dean Raymond round out a proper house music evening.
Who it's for: House music heads, late-night dancers, anyone who appreciates music with texture and warmth
When: Friday, February 20, 2026 | 10:00 PM–4:00 AM | Smartbar (21+)
What it is: The Joffrey Ballet presents "American Icons," a program celebrating four trailblazing choreographers of the 20th century: company co-founders Robert Joffrey and Gerald Arpino alongside other legendary artists. The program showcases dynamic works that defined American ballet, performed at the stunning Lyric Opera House.
Why go: This is world-class ballet in one of America's most beautiful opera houses. The Joffrey's technical precision and artistic vision make every performance an event, and this program specifically honors the choreographers who shaped modern American dance. Multiple showtimes across the weekend mean you can find a performance that fits your schedule.
Who it's for: Dance enthusiasts, classical arts lovers, date-night seekers, anyone who appreciates athletic artistry
When: Friday 7:30 PM, Saturday 2:00 PM & 7:30 PM, Sunday 2:00 PM | February 20–22, 2026 | Lyric Opera House
What it is: The Bulls host two home games at the United Center this weekend—Saturday night against the Detroit Pistons and Sunday evening against the New York Knicks. Whether you're watching Coby White run the point or catching whatever rising talent Detroit's developing, it's live NBA action in one of basketball's most storied buildings.
Why go: United Center games deliver that distinct Chicago sports atmosphere—passionate fans, solid food options, and the chance to see professional basketball up close. The Knicks game especially tends to draw traveling fans, creating a great energy in the building. Gates open 90 minutes before tip-off if you want to watch warmups.
Who it's for: Basketball fans, families, anyone who wants a quintessential Chicago sports experience
When: Saturday, February 21 vs. Pistons at 7:00 PM | Sunday, February 22 vs. Knicks at 7:00 PM | United Center
What it is: Chicago's delightfully unhinged outdoor winter festival returns for its annual freeze-fest outside the Empty Bottle on Cortez Street. This free block party runs from 1 PM until dark, featuring live performances from Los Thuthanaka, Lip Critic, Good Flying Birds, Snuffed, and Body Shop. There's also a preshow Friday and aftershow Saturday night inside the venue.
Why go: Music Frozen Dancing embraces everything absurd about Chicago winters—yes, you'll be cold, but you'll be cold with hundreds of other music lovers while watching great bands. The Empty Bottle's DIY ethos runs through the whole event, and it's completely free. Hot drinks help. Layers are mandatory. Regret is optional.
Who it's for: Indie music fans, the cold-resistant, anyone who thinks outdoor festivals shouldn't end in October
When: Saturday, February 21, 2026 | 1:00 PM until dark | Outside Empty Bottle (1035 N Western Ave)
What it is: Grammy-nominated acid jazz pioneers Liquid Soul bring their Chicago-born sound to Garcia's for a night of jazz, funk, soul, and hip-hop fusion. This collective has been pushing genre boundaries since 1996, blending live instrumentation with DJ scratching and spoken word to create something uniquely their own.
Why go: Liquid Soul is a Chicago institution, and Garcia's intimate setting lets you experience their genre-defying sound up close. This is jazz for people who also love hip-hop, funk for people who appreciate improvisation—a melting pot of Black American musical traditions that never feels pretentious. DJ Jesse De La Peña joins for an extra layer of groove.
Who it's for: Jazz-funk enthusiasts, adventurous music listeners, anyone who wants something genuinely different
When: Saturday, February 21, 2026 | 8:00 PM | Garcia's Chicago
What it is: Mexican grupera superstar Alicia Villarreal—"La Güera"—brings her "Donde Todo Comenzó 2.0" tour to the Rosemont Theatre. As the former lead singer of Grupo Límite and a hugely successful solo artist, Villarreal has been a dominant force in regional Mexican music for three decades. Expect the cumbia, norteño, and grupera hits that made her a legend.
Why go: Villarreal is royalty in regional Mexican music, with a career spanning from the '90s grupera boom to the present day. Her live shows are celebrations—emotional, energetic, and packed with singalong moments. If you grew up on her music or want to experience Mexican pop culture at its finest, this is it.
Who it's for: Regional Mexican music fans, Latinx families, anyone who knows every word to "Te Quedó Grande la Yegua"
When: Friday, February 20, 2026 | 8:00 PM | Rosemont Theatre
What it is: Canadian piano virtuoso Marc-André Hamelin performs a Sunday afternoon recital at Symphony Center, featuring works by Ives, Scriabin, and Schumann. Hamelin is celebrated for his astonishing technique and profound musicality—able to tackle some of the most demanding works in the repertoire while making them feel effortless.
Why go: Hamelin is one of the greatest living pianists, period. His programming is always thoughtful, and hearing him tackle Ives' visionary Concord Sonata alongside Romantic works creates a fascinating musical journey. Orchestra Hall's acoustics are impeccable, and a 3 PM start time means you can make dinner plans afterward.
Who it's for: Classical music lovers, piano enthusiasts, anyone seeking a sophisticated Sunday afternoon
When: Sunday, February 22, 2026 | 3:00 PM | Symphony Center (Orchestra Hall)
Sixteen Candles 22nd Anniversary at House of Blues (Saturday): Chicago's beloved '80s cover band celebrates 22 years of keeping the decade alive. If you want to dance to Duran Duran and Cyndi Lauper covers, this is your party.
Short Shakespeare! Hamlet at Chicago Shakespeare Theater (All weekend): The Bard's tragedy distilled to 75 minutes—all the betrayal and drama, none of the bathroom breaks. Perfect for Shakespeare newcomers or anyone short on time.
Chicago Margarita Crawl (Saturday): It's National Margarita Day weekend, and River North is ready. Multiple bars, tequila specials, and questionable decisions await starting at 4 PM.
DePaul vs. Providence Basketball (Saturday): Catch Big East basketball at Wintrust Arena when the Blue Demons host the Friars at 7 PM. Tickets are typically reasonable for college hoops in a solid venue.
How cold will it be this weekend in Chicago? It's late February—expect highs in the low 30s if you're lucky, with possible wind chill making it feel colder. Layer up, especially for outdoor events like Music Frozen Dancing or the Lunar New Year celebration.
What's the best way to get to United Center? The Blue Line stops at the nearby Illinois Medical District station, about a 15-minute walk. CTA buses also service the area. If driving, parking at the United Center costs $35-40—consider lots on Madison Street for cheaper options.
Are there good dinner options near the Chicago Theatre? The Loop has endless options. Try Italian Village (classic Chicago), Revival Food Hall (fast-casual variety), or Petterino's (pre-theater crowd favorite). Book ahead for post-show if you're seeing Jim Gaffigan.
What if I can't get tickets to The Outsiders this weekend? The show runs through February 22, so this weekend is your last chance in Chicago. Check AllEvents for any last-minute availability or consider the Sunday matinee which sometimes has better availability.
Is the Argyle Lunar New Year festival family-friendly? Absolutely. It's a free, outdoor, all-ages celebration perfect for families. The parade features traditional lion dances that kids love, and there are plenty of food options nearby for all tastes.
How late do the Smartbar and Radius shows go? Smartbar typically runs until 4 AM, while Radius shows usually wrap up around 2-3 AM. Plan your transportation accordingly—Lyft and Uber surge late night.
Chicago's got plenty of reasons to bundle up and brave the cold this weekend. Find more events and plan your outings on AllEvents.
Stay gold, Chicago. 🌬️
