Featured Events in Chicago in May, 2025 (July Updated)

Experience the ultimate Trap Karaoke event in Chicago at the Byline Bank Aragon Ballroom on May 30, 2025. Trap Karaoke: Chicago promises an unforgettable evening filled with live performances, special guests, and non-stop entertainment. Join fellow music enthusiasts at this iconic venue located at 1106 W Lawrence, IL, 60640, for a night of hip-hop karaoke like no other. Don't miss your chance to showcase your skills on stage or simply enjoy the electrifying atmosphere. Get ready to be immersed in the vibrant music scene of Chicago and make memories that will last a lifetime at Trap Karaoke: Chicago.

Showcasing his newest work. Merging various types of creative thoughts and energy with a vibrant results. Making a excellent experience for all ages . Sounds brought to you by : Brian Vaxter Drink specials Information Source: ROME WON / Paint The City Gallery | eventbrite

The Weeknd and Playboi Carti are set to light up Chicago with an electrifying performance at Soldier Field Stadium on May 31, 2025, at 7:00 PM. This highly anticipated event promises an unforgettable night of music and entertainment, featuring two of the biggest names in the industry. The Weeknd, known for his chart-topping hits and mesmerizing stage presence, will be joined by the dynamic and innovative Playboi Carti, creating a unique blend of styles that is sure to captivate the audience. With ticket prices ranging from $43 to $115, fans will have the opportunity to experience this spectacular event at one of Chicago's most iconic venues. Soldier Field Stadium, located in the heart of Chicago, IL, provides the perfect backdrop for an evening of unparalleled musical artistry. Don't miss the chance to witness The Weeknd and Playboi Carti Chicago event, a night that promises to be a highlight of the 2025 concert season.

Chicago Hounds Match Day with Twisted Come join us for an epic day of fun and excitement at the Chicago Hounds Match Day with Twisted event! Happening at 6462 S Central Ave & SeatGeek Stadium. This package includes a suit access game day ticket and a drink package for pre-game party as well as a post game party. Transportation to and from the game is also included. Information Source: Twisted Shamrock Pub | eventbrite

Explore Chicago Cubs v Cincinnati Reds sporting information for 31st May, as well as links for Baseball tickets and more with Fixture Calendar. The Chicago Cubs are an iconic professional baseball team based in Chicago, Illinois. They compete in Major League Baseball (MLB) as part of the National League Central division. The team has a rich history, making their debut in the National League1 in 1876 and claiming three World Series titles in 1907, 1908, and most recently in 2016. The Cubs have consistently performed well, with 18 division titles and 6 National League pennants. The team is known for its loyal fan base and celebrated players, such as legendary Ernie Banks and Sammy Sosa. The Cubs currently play their home games at Wrigley Field, which has been their home since 1916 and is dubbed as the oldest ballpark in the National League. As one of the most beloved and successful National League1 teams, the Chicago Cubs continue to be a force to be reckoned with in the league. The Cincinnati Reds are one of the oldest teams in Major League Baseball, having been founded in 1881. They compete in the Central Division of the National League and have won five World Series titles, the most recent being in 1990. The team has also won the National League pennant nine times, most recently in 1990. The Reds have produced many notable players throughout their history, including legends like Johnny Bench, Joe Morgan, and Pete Rose. Their current roster boasts talented players such as perennial All-Stars Joey Votto and Eugenio Suarez. The team's home stadium, Great American Ball Park, offers a picturesque backdrop for fans to enjoy America's pastime, with stunning views of the Ohio River and the Cincinnati skyline. Catch a game at this iconic stadium and witness the rich history and competitive spirit of the Cincinnati Reds. Information Source: fixturecalendar.com

Buns and Basketball Chicago - May 31st 2025 Join us for a fun-filled day of basketball and delicious buns at our event on May 31st! Whether you're a seasoned player or just looking to have a good time, this event is perfect for everyone. Don't miss out on this exciting opportunity to enjoy some hoops and tasty treats with friends and family. See you there! All ticket purchases, that did not request a refund, will get free entry into the game Information Source: Thickoverload ENT LLC | eventbrite

Across three decades, artist and filmmaker Arthur Jafa has developed a singularly dynamic practice comprising films and videos, photographs, and sculptures. Through his multidisciplinary work, Jafa seeks to encompass what he describes as “the full complexity, specificity, beauty, and potentiality of what Black folks have made and continue to make out of the bleak existential circumstance we’ve attended to over the past several hundred years.” Utilizing found imagery, music, and artistic techniques such as montage and collage, he has constructed an extensive assemblage of Black expression, layered and arranged in ways that reveal the diverse and complex realities of Black being.

Descending the Staircase considers novel artistic approaches to representing the human body. Spread across two floors of the museum, the exhibition presents figures of all kinds, from the fragmented, absurd, and surreal to the curated, self-aware, and media savvy. Puppets, masks, and automatons merge bodies with objects, juxtaposing the animate and inanimate, while abstract sculptures evoke the human form through soft and fleshy materials such as nylon, wax, hair, and latex. Elsewhere, artists deploy the living body as a medium, setting it in motion with performance and gesture. Together, these artworks delve into fundamental questions about the human body in the contemporary world, including its relationship to labor and machines, its presentation in advertising and social media, and its role within the everyday domestic sphere.

This year’s Spring Flower Show, “Rooted in Mystery” explores the critical parts of plants that we don’t usually see – the roots! In addition to finding and delivering water and nutrition to the leaves and stems, roots perform many lesser known but important functions in the lives of plants. For instance, plants “talk” to each other via chemical and electrical signals emitted by their roots to aid in survival. Visitors will learn about the different types of roots and the cool stuff they do while enjoying a marvelous display of spring plants, including azaleas, pansies, snapdragons, astilbe, baptisia, hydrangeas, and 26 different varieties of tulips, daffodils, and hyacinths.

The artist and scholar Tai Xiangzhou masterfully fuses antiquity and contemporary artistry by reinterpreting ancient Chinese jades and bronzes through the meticulous lens of ink painting. Renowned for his deep engagement with classical Chinese painting traditions, the artist shifted his focus from cosmic landscapes—such as those in his 2021 exhibition Cosmoscapes: Ink Paintings by Tai Xiangzhou—to tangible artifacts of China’s rich history. His hyperrealistic paintings magnify the grandeur of ritual vessels and jade ornaments, elevating them to an unprecedented monumental scale, along with the artist’s own inscriptions.

The first exhibition ever to focus on the multiple connections between drawing and printmaking, this presentation brings together around 90 works on paper by some of the greatest artists in the Western tradition to uncover the inner workings of their creative process and offer new ways to think about the links between the two mediums. Featuring fascinating drawings and exceptional prints from the late 15th century though the mid-19th century by artists such as Albrecht Dürer, Parmigianino, Rembrandt, Peter Paul Rubens, Maria Sibylla Merian, Francisco Goya, and William Blake, the exhibition explores the creative exchange between the two practices by showcasing preparatory drawings for prints, printed imitations of drawings, and drawn copies of prints. A selection of hybrid works also questions traditional definitions, strict boundaries, and outdated hierarchical distinctions between media.

Apparitions presents the work of over twenty pioneering artists from across the last century whose interrogations of the human form and its fleeting presence have pushed boundaries of representation. Whether by dematerializing the body, imagining spirits, or making mirages, the artists on view conjure a hallucinatory realm—a liminal space between what appears and what vanishes.

Experience the unparalleled creativity of Reggie Watts Live at Thalia Hall in Chicago on May 1, 2025. Known for his innovative blend of music and comedy, Reggie Watts promises an unforgettable evening of entertainment at this iconic venue located at 1807 South Allport Street, IL, 60608. Don't miss this opportunity to witness one of the most unique performers in the industry showcase his talents live on stage. Make sure to mark your calendars for this exceptional event that is sure to leave you amazed and inspired.

Elvin Bishop (Early) is set to perform at SPACE in Evanston on May 1, 2025. The venue is located at 1245 Chicago Avenue, IL, 60202. This event promises to be a memorable evening filled with the soulful blues and rock music that Elvin Bishop is known for. Don't miss the opportunity to experience this legendary musician live on stage in Evanston. Secure your tickets now to witness a performance that will surely leave you wanting more.

Explore Chicago White Sox v Milwaukee Brewers sporting information for 1st May, as well as links for Baseball tickets and more with Fixture Calendar. The Chicago White Sox are a professional baseball team based in Chicago, Illinois. They compete in the American Family Field0 Division of the American League in Major League Baseball (MLB). The White Sox were founded in 1901 and have since then won three World Series titles, the most recent being in 2005. The team is known for producing numerous talented players, including Hall of Famers such as Frank Thomas and Nellie Fox. Their home stadium is Guaranteed Rate Field, located on the South Side of Chicago. This state-of-the-art stadium has a capacity of 40,615 and has been the host of many major events, including the MLB All-Star Game and the World Series. With a strong history of success and a dedicated fan base, the Chicago White Sox continue to be a force to be reckoned with in the MLB. The Milwaukee Brewers are a professional baseball team based in Milwaukee, Wisconsin. They compete in Major League Baseball (MLB) as a member of the National League American Family Field0 division. The team was founded in 1969 and has since won one World Series championship in 1982 and seven division titles. Some of their top players include Christian Yelich, Lorenzo Cain, and Josh Hader. The team plays their home games at the iconic American Family Field, which has a seating capacity of over 41,000 fans. The Brewers have a loyal fan base and continue to be a strong contender in the competitive world of professional baseball. Information Source: fixturecalendar.com

CHIRP Radio is thrilled to welcome Corridor and Robber Robber to Chicago at The Empty Bottle on May 1, 2025. The venue is located at 1035 North Western Ave, IL, 60622. This highly anticipated event promises an unforgettable night of live music in the heart of the Windy City. Don't miss the opportunity to experience these talented artists in a one-of-a-kind performance. Get your tickets now and join music enthusiasts for a night to remember.

Experience the soulful sounds of R&B at the highly-anticipated R&B INVITATION TOUR in Chicago. Taking place at the prestigious Arie Crown Theater on May 2, 2025, this event promises a night filled with smooth melodies and captivating performances. Located at 2301 Lake Shore Dr At McCormick PL, Chicago, IL, 60616, the venue provides the perfect setting for an unforgettable evening of music. Don't miss out on this opportunity to immerse yourself in the world of R&B with top artists and a passionate crowd.

Experience the mesmerizing music of Lucy Dacus on her "Forever Is A Feeling Tour" in Chicago at The Chicago Theatre on May 2, 2025. The venue is located at 175 N State St, IL, 60601. Don't miss this opportunity to witness a talented artist perform live in one of the city's most iconic theaters. Get ready for a night filled with unforgettable melodies and captivating lyrics. Join fellow music enthusiasts for an evening that promises to leave a lasting impression.

Explore Chicago White Sox v Houston Astros sporting information for 2nd May, as well as links for Baseball tickets and more with Fixture Calendar. The Chicago White Sox are a professional baseball team based in Chicago, Illinois. They compete in the Central Division of the American League in Major League Baseball (MLB). The White Sox were founded in 1901 and have since then won three World Series titles, the most recent being in 2005. The team is known for producing numerous talented players, including Hall of Famers such as Frank Thomas and Nellie Fox. Their home stadium is Guaranteed Rate Field, located on the South Side of Chicago. This state-of-the-art stadium has a capacity of 40,615 and has been the host of many major events, including the MLB All-Star Game and the World Series. With a strong history of success and a dedicated fan base, the Chicago White Sox continue to be a force to be reckoned with in the MLB. The Houston Astros are a professional baseball team based in Houston, Texas. They were founded in 1962 and are members of the American League (AL) West division. The Astros have made it to the World Series twice, winning their first championship in 2017. They have also won seven division titles and one wild card berth. The team has produced many talented players, including former MVPs Jose Altuve and Jeff Bagwell. They also have a strong current roster, led by star players such as Alex Bregman and Justin Verlander. The Astros play their home games at Minute Maid Park, which has a retractable roof and can accommodate over 40,000 fans. Overall, the Houston Astros are a highly competitive team with a history of success, making them a force to be reckoned with in the world of baseball. Information Source: fixturecalendar.com

CHECK BACK FOR RIDE UPDATES! Southside Critical Mass' ride is 1st Fridays at 5:45pm. Come join the ride from Nichols Park (south end, 55th & Kimbark) 1300 E. 55th St, Chicago. Bring mask, helmet, water, money, bike lock, bike lights, jacket. The ride is free. Meet at 5:45pm and ride at 6:15ish. Please be aware that by participating in Southside Critical Mass rides you accept that you are responsible for your bike’s condition, your own fitness to ride and your own safety. The streets may present hazards. Please wear a helmet. Social Pop-up Ride. Route subject to change. Everyone is responsible for themselves. Ride at your own risk. Please ride in a safe manner. Have Fun! Happy Friday! Please like our page and share this post. Thanks! The Southside Critical Mass bike ride meets every 1st Friday of the month at 5:45pm riding at 6:15ish at Nichols Park (Plaza), located at 55th & Kimbark. We do not ride in winter or (December through March) . We normally travel about 15-20 miles at a moderate pace (rolling speed 10-14 mph). Our monthly ride through the Southside of Chicago is focused on using the activity of cycling as a vehicle to make our neighborhoods more bikeable and ultimately more liveable. We support businesses in the area. Facebook: Southside Critical Mass Twitter & Instagram: Southside Critical Mass Information Source: Southside Critical Mass Chicago | eventbrite

Experience the electrifying performance of Bad Nerves with Spiritual Cramp at Thalia Hall in Chicago on May 2, 2025. This highly anticipated event promises an unforgettable night of music at 1807 South Allport Street, IL, 60608. Don't miss your chance to witness these talented acts live on stage in one of Chicago's premier music venues.

Presented by Jigsaw Dating x SPIN Limited tickets available! Please arrive on time and find the Jigsaw host stand to check in. Check in will close 45 minutes after the start time. Enjoy: Mixer-style mingling with local singles, everyone in our party is looking for the same thingFree ping pong play, included with your ticket!Signature ping pong themed bingo activity (+ prizes for the first 5 to get BINGO)Custom conversation cards to help you break the iceDedicated host on site to greet + check you inComplimentary welcome drink (for Jigsaw app members only!)Tickets are nonrefundable. Must be single and 21+ with valid ID. NAME PROVIDED MUST MATCH ID. Contact events@jigsaw.co for questions. Jigsaw member perks: FREE monthly members-only ticket to any singles event across the country, complimentary welcome drink, skip the line add on, exclusive ticket protection (event credits), and so much more! Information Source: Jigsaw® Dating | eventbrite

Explore Chicago Fire FC v Orlando City SC sporting information for 3rd May, as well as links for Football tickets and more with Fixture Calendar. Chicago Fire FC is a professional soccer team based in Chicago, Illinois, and competes in the Major League Soccer (MLS) Eastern Conference. Founded in 1997, the team has won one United States0 Cup in 1998 and four US Open Cups in 1998, 2000, 2003, and 2006. The team's home stadium is the Soldier Field, which has a capacity of 61,500 seats. Some notable players who have played for the Chicago Fire FC include Bastian Schweinsteiger, Cuauhtémoc Blanco, and DaMarcus Beasley. The team is currently led by head coach Raphael Wicky and has a strong lineup with players such as Robert Berić, Luka Stojanović, and Francisco Calvo. With a strong history and competitive roster, Chicago Fire FC is a top contender in the United States0. Orlando City SC is a professional soccer team based in Orlando, Florida. The team was founded in 2013 and currently competes in Major League Soccer (MLS), the top tier of the United States and Canada's soccer pyramid. The team is one of the newest members of United States0, but has quickly made a name for themselves with their competitive gameplay and enthusiastic fan-base. Orlando City SC's home stadium is the Orlando City Stadium, which can hold up to 25,500 fans. The team has a strong roster of talented players, including notable names such as Nani and Mauricio Pereyra. In their short time in United States0, Orlando City SC has already secured multiple playoff appearances and earned the respect of their fellow teams. With their determination and skill, this team is sure to continue making waves in the world of professional soccer. Information Source: fixturecalendar.com

Explore Chicago White Sox v Houston Astros sporting information for 3rd May, as well as links for Baseball tickets and more with Fixture Calendar. The Chicago White Sox are a professional baseball team based in Chicago, Illinois. They compete in the Central Division of the American League in Major League Baseball (MLB). The White Sox were founded in 1901 and have since then won three World Series titles, the most recent being in 2005. The team is known for producing numerous talented players, including Hall of Famers such as Frank Thomas and Nellie Fox. Their home stadium is Guaranteed Rate Field, located on the South Side of Chicago. This state-of-the-art stadium has a capacity of 40,615 and has been the host of many major events, including the Chicago White Sox0 All-Star Game and the World Series. With a strong history of success and a dedicated fan base, the Chicago White Sox continue to be a force to be reckoned with in the Chicago White Sox0. The Houston Astros are a professional baseball team based in Houston, Texas. They were founded in 1962 and are members of the American League (AL) West division. The Astros have made it to the World Series twice, winning their first championship in 2017. They have also won seven division titles and one wild card berth. The team has produced many talented players, including former MVPs Jose Altuve and Jeff Bagwell. They also have a strong current roster, led by star players such as Alex Bregman and Justin Verlander. The Astros play their home games at Minute Maid Park, which has a retractable roof and can accommodate over 40,000 fans. Overall, the Houston Astros are a highly competitive team with a history of success, making them a force to be reckoned with in the world of baseball. Information Source: fixturecalendar.com

Join us for a Kentucky Derby soiree atThe Reveler! Saturday, May 3rd • 3:00 PM Your general admission ticket includes entry, your welcome Carbliss Seltzer, giveaways, and your entry into our best dressed contest for the chance to win a 3-night stay at Circa Last Vegas! The fun begins at 3pm! Dress to the nines for your chance to win Best Dressed and Best Hat! LIMITED TABLES AVAILABLE! You can have more guests join than the table is designed for; it's meant to be a home base for your group. Seating is not guaranteed for all members of the group. Tables must be claimed within 1 hour of the event beginning and is yours until 6pm. Thank you to our featured brands, Woodford Reserve and Carbliss Cocktails, and our sponsor, Circa Resorts & Casino Las Vegas! Must be 21+ to enter. Must provide VALID ID. We will also be open as usual for regular walk-in guests during this event! Information Source: The Reveler | eventbrite

Don't miss the exclusive performance by Clap Your Hands Say Yeah, presenting their debut album at Thalia Hall in Chicago. Joining them on stage will be Knifeplay and La Zorra Zapata for an unforgettable night of music on May 3, 2025. The venue, located at 1807 South Allport Street, IL, 60608, promises a memorable experience for all attendees. Get ready to immerse yourself in a night of captivating melodies and energetic performances.

Join us for a Kentucky Derby soiree atWillie Lill's! Saturday, May 3rd • 3:00 PM Your general admission ticket includes entry, your welcome Long Drink cocktail, giveaways, and your entry into our best dressed contest for the chance to win a 3-night stay at Circa Last Vegas! The fun begins at 3pm! Dress to the nines for your chance to win Best Dressed and Best Hat! LIMITED TABLES AVAILABLE! You can have more guests join than the table is designed for; it's meant to be a home base for your group. Seating is not guaranteed for all members of the group. Tables must be claimed within 1 hour of the event beginning and is yours until 6pm. Thank you to our featured brands, Journeyman Distillery and Long Drink Cocktails, and our sponsor, Circa Resorts & Casino Las Vegas! ***Must be 21+ to enter. Must provide VALID ID*** We will also be open as usual for regular walk-in guests during this event! Information Source: Willie Lill's | eventbrite

Heather McMahan brings her highly anticipated "The Bamboozled Tour" to Chicago on May 3, 2025, at the prestigious Chicago Theatre located at 175 N State St, Chicago, IL, 60601. Fans can expect an unforgettable evening filled with laughter and entertainment as Heather McMahan showcases her unique comedic talents on stage. Don't miss out on this opportunity to experience one of the most talked-about comedy tours of the year in the vibrant city of Chicago.

oin us for a Kentucky Derby soiree atBlue Bayou! Saturday, May 3rd • 3:00 PM Your general admission ticket includes entry, your welcome High Noon, giveaways, and your entry into our best dressed contest for the chance to win a 3-night stay at Circa Last Vegas! The fun begins at 3pm! Dress to the nines for your chance to win Best Dressed and Best Hat! LIMITED TABLES AVAILABLE! You can have more guests join than the table is designed for; it's meant to be a home base for your group. Seating is not guaranteed for all members of the group. Tables must be claimed within 1 hour of the event beginning and is yours until 6pm. Thank you to our featured brands, WhistlePig Whiskey and High Noon, and our sponsor, Circa Resorts & Casino Las Vegas! Must be 21+ to enter. Must provide VALID ID. We will also be open as usual for regular walk-in guests during this event! Information Source: Blue Bayou | eventbrite

Kneebody will be performing at SPACE in Evanston on May 3, 2025. The venue is located at 1245 Chicago Avenue, IL, 60202. Kneebody is a modern jazz band known for their innovative and dynamic sound. Don't miss this opportunity to experience their unique blend of jazz, rock, and electronic music live on stage. Get your tickets now for an unforgettable evening of musical artistry.