This weekend in Chicago, IL

At O’Hare International Airport, the annual plane pull rallies teams and supporters to benefit Special Olympics Illinois. Groups of twenty work together to move a 95,000-pound aircraft twelve feet in the fastest time, creating a spirited showcase of strength, teamwork, and community. The day features the full-size plane pull competition, food trucks and concessions, a live DJ with entertainment, activities for kids, and raffles with giveaways. Teams can register or join an existing lineup, fundraising is encouraged, and spectators are welcome to cheer on the action. This family-friendly gathering supports a meaningful cause and offers a unique experience for all ages.

Celebrating its 11th year, this family friendly trail run showcases the Bloomingdale Trail while supporting the mission of Friends of the Bloomingdale Trail. Participants can take on a timed 5K along the elevated path with city views, and young runners can sprint in quarter mile and half mile dashes. Packet pickup, check in, and the start and finish are based at McCormick YMCA near the trail’s western end. On event day, expect a kids activity station, live music, snacks and beverages, sponsor activations, and a post race gathering with awards and refreshments. Event details are subject to change.

Enjoy an uplifting yoga session surrounded by the serenity of the Judy Istock Butterfly Haven. The class is designed to leave participants feeling energized and balanced, with inspiration to carry their practice beyond the mat and into everyday life. Please bring your own mat. Participants must be 18 or older. Advance online registration is required and drop-ins are not accepted. Museum admission is included with the ticket.

The 10th stop of the Players Grass Series brings an Oktoberfest-themed volleyball tournament to Chicago. Divisions include men’s 3’s at AA, A, BB, and B, women’s 3’s at AA, A, BB, and B, coed 4’s at BB, B, and Rec with no more than two men on the court at a time, and a new 4’s Rec division open to any gender lineup. Registration features pool play that sends top teams to the playoffs, friendly tournament staff, and pool matches consisting of two sets to 21 points. Prizes range from Players Champs apparel to entries for future tournaments, and the highest men’s and women’s 3’s divisions offer cash payouts. Captains are required to list every player on the online roster, and all participants must complete an electronic waiver before playing. Coed divisions follow a maximum of 50 percent men on the court, while men’s and women’s divisions are single gender as listed. Teams may register under a captain who manages the roster and team fee, with a Team Payer option to assign individual shares for teammates to pay online. The event also highlights a welcoming community vibe with opportunities to make lasting connections.

This free Hispanic heritage genealogy program welcomes both first-time explorers and experienced researchers. It begins with a keynote presentation from professional genealogist Moises Garza, sharing practical steps to start or deepen family history work. After the talk, light refreshments will be available and there will be time to connect with other participants. The program continues with small-group breakout sessions led by experienced family history specialists who offer personal guidance to help attendees make meaningful progress on their own genealogy. Registration links will be shared soon.

The 61st Street Farmers Market moves outdoors with more than 30 vendors featuring fresh produce, baked goods, prepared foods, and locally made products. Weekly activities include a chef demonstration, Market School, Sprout Station, and Blackstone Bicycle Works’ Open Shop. SNAP is accepted and matched through Link Match for fruits and vegetables; look for the red tent in the middle of the market to use SNAP benefits.

Celebrate the launch of two neighborhood markets as the new Midway Retail Market debuts alongside the Garfield Ridge Farmers Market. Visitors can browse offerings from local small businesses, enjoy fresh baked treats with coffee, and shop farmers market staples along with handmade, one of a kind finds. The atmosphere is welcoming and community centered. The season starts with a select group of vendors and will grow over time, giving shoppers a chance to support these sellers from the very beginning. Every purchase helps fuel local dreams.

Explore the Art Institute of Chicago through the lens of Ferris Bueller’s Day Off on a 90-minute guided walking tour. Spanning three floors, it spotlights 16 artworks and connects them to the film’s characters while examining how the camera frames these pieces on screen. Attendees can expect to leave with an appreciation for the art and its cinematic ties. Admission to the Art Institute is not included.

Bright Star Circus presents a circus themed variety show created for families and fans of live entertainment of all ages. Each performance features a rotating roster of premier talent, so every show brings something new. The stage comes alive with magicians performing mind bending feats, musicians setting the rhythm, comedians and clowns delivering big laughs, and dancers alongside other variety artists who keep the energy high. It is a colorful celebration of imagination, filled with surprises, laughter, and theatrical joy.

¡Gritos! de Independencia 2026 brings live music together with complimentary food available at restaurants across Belmont Cragin. Tickets are free and can be reserved through the provided link.

Indie Park Fest returns for its fifth year, creating a relaxed day-in-the-park atmosphere while spotlighting inventive local acts from across Chicago. Performers span the musical spectrum, offering an eclectic mix for listeners of all kinds. The vibe is casual and picnic friendly, and the focus stays on supporting homegrown talent throughout the day. The festival is self-produced and sustained by community support, with a recommended $20 donation that goes directly to the artists and helps keep the event thriving. Expect vendors, activities for kids, and plenty of live music. Lunar Ticks, an improvisational and alternative rock band rooted in the Irving Park neighborhood, collaborate with the Independence Park Advisory Council and the Chicago Park District to present this community-centered celebration.

Raise a glass for a good cause at a spirited pub crawl that supports the cats of Harmony House. Expect beachy vibes and margaritas as you help provide shelter and care for Chicago’s homeless cats and kittens. The celebration begins at Harmony House for Cats with a courtyard pre-party where participants can pick up a swag bag, an event T-shirt, and fun flair, along with treats and refreshments. From there, the route heads to four hip Avondale spots, with planned stops at Wolfhound, DMen, Beer Temple, and Frank & Mary’s Tavern. Along the way, enjoy complimentary drink specials, free snacks, games, raffles, prizes, and a few surprises, plus time afterward to visit with the cats. Tickets cost $55 and are on sale, with T-shirt sizes guaranteed only for purchases made by the stated deadline. Participants must be 21 or older and should bring a valid ID. Sponsorship inquiries can be sent to events@hhforcats.org.

Experience an onstage conversation with Emily St. John Mandel, the bestselling novelist behind Station Eleven. Presented by Chicago Humanities in collaboration with Thalia Hall, this program takes place at Thalia Hall.

At Gallagher Way in Wrigleyville, WingOut Chicago brings together top wing restaurants for a weekend of tasting, music, and friendly competition. Guests can try a wide range of flavors, including classic buffalo, sweet and spicy, wood smoked, jerk, and honey chili, with many more to explore. Live soul, R&B, and reggae performances set the soundtrack, adult beverages are available, and a fan vote helps decide Chicago’s top wings alongside judging by local celebrities.

Discover museum highlights during a 45-minute tour conducted in American Sign Language, designed for members of the Deaf community. The experience explores the intersection of history, science, and community that shapes the Field Museum. Meet at the Monumental Poles in Stanley Field Hall to begin. No RSVP is required.

Riverside Hop Stop returns as a collaboration between Riverside Foods and the Olmsted Society of Riverside, offering a commemorative tasting glass and the chance to sample more than twenty beverages from local breweries, cideries, and cocktail makers, including Riverside’s Quincy Street Distillery. Enjoy Greek food vendors, family-friendly entertainment from Pocket Circus, and live music from Riverside DJ Mattio in the arboretum Village of Riverside. Complimentary bicycle valet is available, designated drivers are encouraged, and Metra provides convenient access. This nonprofit, zero waste gathering supports local beautification, cleaner air, and climate-positive projects through the Olmsted Society of Riverside, a 501(c)(3).

Wonderful Woman Wednesday Chicago presents the 8th Annual Chicken & Champagne Soiree, a warm celebration of connection, empowerment, and purpose. Attendees can meet and network while supporting a cause, as donations go toward the organization’s scholarship fund benefiting two Class of 2027 graduates preparing for college. The organizers extend heartfelt thanks for continued support and generosity. Tickets are available by advance purchase only.

A day dedicated to indie anthems features global DJs, the drive of live drums, and vibrant visuals, supported by full-scale festival lighting and production. The soundtrack covers staples of the scene, from Arctic Monkeys to The Strokes, creating a high-energy salute to everything indie.

Thee Sacred Souls performs live at the Salt Shed Fairgrounds. Doors open ahead of the show, offering time to get settled before the music begins.

Booker Prize winning author Marlon James appears at Thalia Hall to discuss his new novel, The Disappearers. From Chicago Humanities in collaboration with Thalia Hall, this event offers a chance to hear directly from the writer as he talks about his latest work.

Sapphic Saturday at Sidetrack is a no cover celebration of women who love women, filling the Main & Cherry Bar with music centered on queer women, high energy drag from Kari Bunne with a special guest, party games, and more. Created for lesbians and those who love them, the night highlights and supports the local lesbian community in a welcoming atmosphere. This recurring party takes place on the final Saturday of each month.

Proksa Park comes alive for the Berwyn Lantern Parade, a free, all-ages celebration of creativity and community. Enjoy live music and a friendly atmosphere, whether you plan to walk with a lantern or watch as a spectator. Attendees are encouraged to bring a lantern, and a limited number will be available at the park. The event is open to residents, visitors, schools, local organizations, and businesses. Keep an eye out for related workshops and resources to help you prepare.

Reggies Rock Club hosts a three-band lineup featuring Greenleaf, Howling Giant, and Psython. The show is open to ages 17 and up. Doors open before the performance, with live sets from all three artists on the club stage.

This event features the film that earned six Academy Award nominations, including Best Picture and Best Original Song, and won for Best Sound. The story follows Pete “Maverick” Mitchell, portrayed by Tom Cruise, a veteran Navy test pilot tasked with preparing a select group of TOPGUN graduates for a mission unlike any they have faced. Among them is Lt. Bradley “Rooster” Bradshaw, played by Miles Teller, the son of Maverick’s late friend and Radar Intercept Officer, Goose. As the team readies for a high-risk operation, Maverick must reckon with the past and guide his pilots through a challenge that could require the ultimate sacrifice.

Artango Bar & Steakhouse presents an evening of live Brazilian jazz led by singer and musician Luciano Antonio. Experience soulful melodies and the lively spirit of Brazil as his performance fills the room with rich rhythm and color. Seating is limited.

At Garcia's Chicago, The Polish Ambassador blends original material with fresh interpretations of Phish songs for a set that pairs new sounds with reimagined favorites. A General Admission dance pit is located directly in front of the stage. Seating options include Premium Tables closest to the stage with table service and Reserved Tables on the main floor behind Premium, also with table service. Both table sections are cabaret style, so you may be seated with other fans. Private booths are offered and accommodate different group sizes depending on the booth. General Admission standing areas line the sides of the room on an elevated level for clear views and easy bar access. All sales are final, refunds and exchanges are not available, and tickets may be transferred through your TM Account. Garcia's is fully ADA compliant with wheelchair lifts and ramps between levels, assisted listening devices upon request, and access for official service animals.

Second Hand Soul Band sets the vibe in Chicago’s Edison Park with a dance-friendly show at a restaurant where the music and the menu share the spotlight. Bartenders are ready to mix favorite drinks, and there is plenty of space to hit the dance floor. Reservations are strongly recommended.

Pop up karaoke returns to the large back room at Dante's Tavern, also known as High Dive, bringing back an old-school sing-along vibe with a refreshed twist.

At Las Fuentes in Lincoln Park, Saturday nights bring Mexico, Puerto Rico, and the Dominican Republic together on a single dance floor, blending music, movement, and culture in one lively celebration. Three distinct rhythms and identities meet in a shared space, all united by the beat. Expect a rotating Cumbia, Bachata, or Salsa lesson each week, followed by continuous DJ-driven energy that carries into after hours. DJ Double O curates Salsa, Bachata, and tropical selections, later weaving in Rock en Español, Latin dance, and Reggaeton. A dedicated burst of all-Cumbia excitement, Cumbia Happy Time, keeps the floor moving at peak intensity. Birthday groups of five or more can reserve a package in advance that includes a complimentary bottle of champagne, a cake with candle, a reserved table, and an optional birthday dance. Availability is limited each weekend.

Performers from One Group Mind make up the show in real time, starting with one suggestion from the audience and shaping it into complete comedic pieces. The venue has been recognized by ChooseChicago, Chicago Magazine, Secret Chicago, and Time Out Chicago in roundups highlighting Chicago’s leading comedy clubs. Featured performers include Blair Resse, Carter Naughton, Emily Patterson, Emma Anderson, Eric Iannelli, Felix Cortes, Gabriella Dedmore, Heather Barnwell, Joseph Schmidt, Mara Baldwin, MariGrace Russo, Olivia Eldert, Ricky Arias, Sophie Crafton, Vanessa Chisakula, and Zachary Knight.

Regional growers, food makers, artisans, and neighborhood businesses come together in Wicker Park for a community market centered on sustainability. Browse responsibly grown produce and nutritious foods made with ingredients from nearby farms, sold straight from the people who grow and craft them. The market fosters entrepreneurship by offering a direct-to-consumer platform where vendors can sell, talk with visitors about eating well and sourcing sustainably, and form connections with neighbors. Artisans, performers, and service providers also take part, helping strengthen community ties, support a resilient local economy, and highlight the character of Wicker Park.

Part of a summer series, this volunteer run, community focused farmers market features music and ready to eat food. Free yoga classes are offered, with preregistration available on the website. A vendor list organized by date is also available on the website.

Greater Chicagoland Pagan Pride returns to Riis Park to bring the Pagan community together in a welcoming outdoor gathering. Admission is a donation to Nourishing Hope, and complimentary parking is available in the lots. People of all faiths are welcome, including families and friends. Expect updates on vendors, workshops, entertainers, rituals, and other activities as details are confirmed.

A neighborhood celebration honoring Avondale’s history and the many cultures that shaped it, with a focus on community connections, creativity, and food. Expect live music, local and global cuisine with a potluck, hands-on arts and cultural crafts, community vendors and spotlight features, bike decorating followed by a parade, chalk art, face painting, and more. Activities also include bike ambassadors, yoga, free cycle, and dedicated cultural programming. The gathering encourages getting to know more neighbors by name, which research links with greater safety, while deepening appreciation for the stories and traditions that make Avondale special. Family friendly and free to attend.

A festive pop-up at Midway Marketplace honors Hispanic heritage and culture while spotlighting community and neighborhood businesses. Rescheduled due to weather, the celebration fills the Retail Sheds with a mix of local food, retail, and artisan vendors. Guests can also enjoy complimentary rounds of Lotería hosted by MarGo’s Treasures, with prizes available. Bringing a personal chair is encouraged for comfort. A one hour yoga class will be offered inside the BizHub, with advance registration required and a $10 fee. An updated vendor lineup will be shared before the event as confirmations are finalized, creating a welcoming space to shop local, play, and celebrate together.

An uplifting program at the International Museum of Surgical Science focuses on breast health, empowerment, education, and resilience while celebrating the launch of the book “I’m Limitless.” This benefit for the United Colors of Pink Breast Cancer Foundation combines a healthy-breast seminar with talks from Dr. Violette Kolcan, OMD, LAc, Dr. Paul Hannah, a board certified psychiatrist and holistic physician, Dr. Peter Brukasz, MD, DABVLM, Dr. Rita Rios, president and CEO of Bollinbrook Spa, Joanna Pop, president of Devonshire Montessori School, and Dr. Martha Razo, XBS founder. Guests can expect music and lunch, along with a copy of “I’m Limitless” included. The event is organized by Women Empower The World Magazine, Longevity in New Era, Ancient Healing Holistic Medicine, DoctorViolette.com, and Violette Kolcaan.

Docents from the Olmsted Society lead a guided North Tour through Riverside, Illinois, a National Historic Site designed by Frederick Law Olmsted and known as the nation’s first planned suburb. The walk highlights charming parks, curving streets, lush landscaping, and historic homes while sharing the story behind the community’s design. Tickets are $25 per person, with a $20 rate for seniors 62 and older and for Olmsted Society members. Payment can be made in advance online or with cash or check on the day of the tour. Custom tours are available by appointment for $30 per person.

Seasonal workdays at the Children’s Garden in Proksa Park offer hands-on ways to care for the space on select Sundays during the growing season. Tasks change with the time of year, and participants of all ages and ability levels are welcome. No prior gardening experience is needed, as volunteers will be on hand to provide guidance and help coordinate activities. Minors must attend with a responsible adult. A monthly garden swap and tool exchange also takes place during the season. Attendees can bring extra plants and surplus gardening tools or accessories to trade with the community. The Children’s Garden is located in the northeast corner of the park.

Dying Fetus and Sanguisugabogg perform at House of Blues Chicago. The venue is standing room only, and tickets are general admission unless otherwise noted. This event is for ages 17 and older. A current, unexpired photo ID is required for entry, such as a driver’s license, state ID, or passport. Supporting acts may change without notice.

Settle into a restorative 90-minute sound bath at the Japanese Culture Center, where singing bowls, gongs, flute, bells, drums, and handpan create a flowing symphony of vibration that encourages deep rest and gentle inner renewal. Participants recline comfortably and allow layered tones and frequencies to support the release of physical tension, clear stagnant energy, and invite calm, clarity, and contentment across mind, body, heart, and spirit. A full gong immersion features three distinct instruments: a Sun Gong tuned to OM that nourishes life force, an Atlantis Gong that promotes emotional balance, and a Blue Stargate Gong resonant with Earth’s frequency and centered on the heart. Reflection and integration are included so intentions can be anchored after the journey. Many participants look for benefits such as shifting brainwave states, enhanced meditation, increased awareness, release of emotional blockages, support for physical healing, and a more balanced nervous system. The experience is guided by Simon Jay Cervania, founder of the Harmonic Waves Healing Accredited Certification Program, a multidisciplinary artist and musician, and a Reiki Master Teacher with more than 15 years in holistic health, sound healing, brainwave entrainment, biofield energy therapy, and trauma release. Born in the Philippines and based in Chicago, he shares his work internationally across cultural centers, yoga studios, and holistic wellness communities. Comfortable clothing is recommended, and items that enhance relaxation such as a yoga mat, blanket, pillow, bolster, or eye pillow are welcome. Early bird admission is $35, same day entry is $40 if space allows, and capacity is limited.

Karaoke takes center stage at The Arrogant Frog Bar in Lincoln Park on the last Sunday of each month. Participants choose their songs and step up to the mic in an upscale dive bar setting. This recurring night is geared toward karaoke fans who want to share the stage with friends and keep the music going month after month.

Cavetown takes the stage at The Salt Shed for a live concert.

Beat Kitchen hosts a show presented by Kickstand Productions featuring performances by Unsane, The Crosses, and Rollo Tomasi. This event is for ages 17 and older.

Sara Bareilles brings The Good Grief Tour to The Chicago Theatre for an evening of live performance. Ticket prices are all-in with fees included before any applicable taxes. Resale tickets can be priced above face value and those prices are not determined by the artist team. No portion of the ticket price is tax-deductible. In partnership with PLUS1, $1 from each ticket sold for this Chicago Theatre show that is not refunded will be contributed by Live Nation to the JED Foundation to support programs that protect emotional health and help prevent suicide among teens and young adults. Attendees should plan to arrive 60 minutes before showtime for entry screening. Bags, including briefcases and handbags, will be checked at the door. By purchasing tickets, guests agree to follow the health and safety measures in place at the time of the event, and these requirements may change based on government mandates and venue protocols. The performance may include immersive elements such as flashing or strobe lights.

Deliverance brings The Corner of Musical Freedom to Renaissance Bronzeville, featuring Mike Dunn. There is a $5 cover at the door. The event is engineered by Thewaywewere Productions.