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

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.

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

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.

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.

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

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

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.

Iman Issa’s Heritage Studies are displays based on historical artifacts, which attempt to communicate their significance to the present moment. In her process, the objects are altered: Issa changes their materials, scale, and color to a degree that the resemblance between the historic artifact and Issa’s work can be difficult to discern. Despite these dissimilarities, the artist insists on the equivalence of these objects, almost like the equivalence between a photograph and its subject.

Paul Pfeiffer: Prologue to the Story of the Birth of Freedom presents 25 years of work from artist Paul Pfeiffer (b. 1966, Honolulu, HI; lives in New York, NY), whose practice interrogates ideas of spectacle and mass culture. By repurposing the tools and systems of media production—including editing, staging, and outsourcing—Pfeiffer recontextualizes global celebrities such as pop stars, film actors, and athletes to reveal relationships between audiences and athletes. icons. As the artist puts it, “who’s using who? Is the image making us, or do we make images?”

Paul Pfeiffer: Prologue to the Story of the Birth of Freedom presents 25 years of work from artist Paul Pfeiffer (b. 1966, Honolulu, HI; lives in New York, NY), whose practice interrogates ideas of spectacle and mass culture. By repurposing the tools and systems of media production—including editing, staging, and outsourcing—Pfeiffer recontextualizes global celebrities such as pop stars, film actors, and athletes to reveal relationships between audiences and athletes. icons. As the artist puts it, “who’s using who? Is the image making us, or do we make images?”

Iman Issa’s Heritage Studies are displays based on historical artifacts, which attempt to communicate their significance to the present moment. In her process, the objects are altered: Issa changes their materials, scale, and color to a degree that the resemblance between the historic artifact and Issa’s work can be difficult to discern. Despite these dissimilarities, the artist insists on the equivalence of these objects, almost like the equivalence between a photograph and its subject.

Iman Issa’s Heritage Studies are displays based on historical artifacts, which attempt to communicate their significance to the present moment. In her process, the objects are altered: Issa changes their materials, scale, and color to a degree that the resemblance between the historic artifact and Issa’s work can be difficult to discern. Despite these dissimilarities, the artist insists on the equivalence of these objects, almost like the equivalence between a photograph and its subject.

Iman Issa’s Heritage Studies are displays based on historical artifacts, which attempt to communicate their significance to the present moment. In her process, the objects are altered: Issa changes their materials, scale, and color to a degree that the resemblance between the historic artifact and Issa’s work can be difficult to discern. Despite these dissimilarities, the artist insists on the equivalence of these objects, almost like the equivalence between a photograph and its subject.

Paul Pfeiffer: Prologue to the Story of the Birth of Freedom presents 25 years of work from artist Paul Pfeiffer (b. 1966, Honolulu, HI; lives in New York, NY), whose practice interrogates ideas of spectacle and mass culture. By repurposing the tools and systems of media production—including editing, staging, and outsourcing—Pfeiffer recontextualizes global celebrities such as pop stars, film actors, and athletes to reveal relationships between audiences and athletes. icons. As the artist puts it, “who’s using who? Is the image making us, or do we make images?”

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

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.

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

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.

What: 3RUN2 x New Balance Group Run Where: Side Practice Coffee (5139 N Damen) When: Sunday, 5/4/2025, 9:00 AM Details: Start/finish the run at the Side Practice Coffee ~5k RunLight Bag DropOption to demo the FuelCell Rebel v4 and FuelCell Super Comp Trainer v3Post-Run Musubi (while supplies last)RafflesMust sign up in advance as capacity is limited Information Source: Three Run Two® / 3RUN2® | eventbrite

Don't miss the captivating performance by Deb Talan with Auralai at SPACE in Evanston on May 4, 2025. Immerse yourself in the enchanting melodies of these talented musicians at 1245 Chicago Avenue, IL, 60202. This event promises to be a night to remember, filled with soulful music and an unforgettable atmosphere. Join us for an evening of musical bliss at this unique and intimate venue in the heart of Evanston.