| Date | Time | Event Name | Type | Genre | Venue | Address | Age | Price | |
|---|---|---|---|---|---|---|---|---|---|
 | SunFeb 8 | 11:30 AM | The Rock and Roll Playhouse plays Music ... | Music | Rock | Thalia Hall | 1807 S Allport St | All Ages | Free |
 | SunFeb 8 | 1:00 PM | Stereophonic (Chicago) | Art & Theatre | Theatre | CIBC Theatre | 18 West Monroe | All Ages | Free |
 | SunFeb 8 | 2:00 PM | Myopic Books X Empty Bottle Book Club: “... | Art & Theatre | Empty Bottle | 1035 N. Western Ave. | All Ages | Free | |
 | SunFeb 8 | 2:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
 | SunFeb 8 | 5:30 PM | Kingston Mines "Blues Jam" with Mike Whe... | Music | Blues | Kingston Mines - Chicago Blues Center | 2548 North Halsted | All Ages | Free |
 | SunFeb 8 | 5:30 PM | The Big Game and Concert and Commercials | Sports | Empty Bottle | 1035 N. Western Ave. | All Ages | Free | |
 | SunFeb 8 | 6:30 PM | Enjambre | Music | Latin | House of Blues Chicago | 329 N Dearborn St | All Ages | Free |
SunFeb 8 | 12:00 AM | The Chicago Theatre Tour Experience | Art & Theatre | Undefined | The Chicago Theatre Tour Experience | 175 N State St | All Ages | Free | |
 | MonFeb 9 | 9:00 PM | FREE MONDAY w/ Modern Cults / Jack Brere... | Music | Other | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
 | TueFeb 10 | 6:00 PM | Angel Bat Dawid | Music | Harris Theater | 205 East Randolph Drive | All Ages | Free | |
 | TueFeb 10 | 6:00 PM | DePaul Blue Demons Womens Basketball vs.... | Sports | Basketball | Wintrust Arena | 200 E Cermak Road, Chicago, IL 60616 | All Ages | Free |
 | TueFeb 10 | 6:30 PM | SZN4 - NEXT STOP: THE TOUR | Music | R&B | House of Blues Chicago | 329 N Dearborn St | All Ages | Free |
 | TueFeb 10 | 7:00 PM | Cosi Fan Tutte | Art & Theatre | Opera | Civic Opera House | 20 N. Wacker Dr. | All Ages | Free |
| TueFeb 10 | 7:00 PM | The Runarounds | Music | Riviera Theatre- IL | 4750 N. Broadway | All Ages | Free | |
| TueFeb 10 | 7:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
 | TueFeb 10 | 7:00 PM | The Outsiders (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| TueFeb 10 | 7:00 PM | Hamnet | Art & Theatre | Chicago Shakespeare Theater | 800 East Grand Avenue on Navy Pier | All Ages | Free | |
 | TueFeb 10 | 7:30 PM | Joyce DiDonato in Emily ??? No Prisoner ... | Art & Theatre | Opera | Orchestra Hall - IL | 220 S. Michigan Ave. | All Ages | Free |
 | TueFeb 10 | 8:00 PM | Covington Groove, Uncle Sexy and Friends | Music | Rock | Reggies Music Joint | 2105 South State Street | All Ages | Free |
| TueFeb 10 | 8:00 PM | Monetochka | Music | Park West | 322 W. Armitage | All Ages | Free | |
| TueFeb 10 | 9:00 PM | G'Nite (Ep Release) / Free Range / Al Sc... | Music | Other | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
| WedFeb 11 | 1:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
 | WedFeb 11 | 2:00 PM | Salome | Art & Theatre | Performance Art | Civic Opera House | 20 N. Wacker Dr. | All Ages | Free |
 | WedFeb 11 | 6:00 PM | Chicago Public League | Sports | Basketball | Credit Union 1 Arena at UIC | 525 South Racine | All Ages | Free |
| WedFeb 11 | 7:00 PM | The Outsiders (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| WedFeb 11 | 7:00 PM | Hamnet | Art & Theatre | Chicago Shakespeare Theater | 800 East Grand Avenue on Navy Pier | All Ages | Free | |
| WedFeb 11 | 7:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
 | WedFeb 11 | 7:30 PM | Opeth (18 and Over) | Music | Rock | Riviera Theatre- IL | 4750 N. Broadway | All Ages | Free |
| WedFeb 11 | 8:00 PM | Midnight In Harlem | Music | Rock | Reggies Music Joint | 2105 South State Street | All Ages | Free |
| WedFeb 11 | 9:00 PM | Stalled / Naomi 10 Million / Laliberté | Music | Other | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
 | WedFeb 11 | 12:00 AM | DePaul Blue Demons Mens Basketball vs. C... | Sports | Basketball | Wintrust Arena | 200 E Cermak Road, Chicago, IL 60616 | All Ages | Free |
| ThuFeb 12 | 5:30 PM | Three Top Happy Hour | Networking | Three Top Lounge | 1357 N Elston Avenue | All Ages | Free | |
ThuFeb 12 | 6:00 PM | Chicago Comedy Club | Art & Theatre | Comedy | Foundation Room at House of Blues Chicag... | 329 N Dearborn St | All Ages | Free | |
| ThuFeb 12 | 6:00 PM | Sheryl Youngblood Band/Nicholas Alexande... | Music | Blues | Kingston Mines - Chicago Blues Center | 2548 North Halsted | All Ages | Free |
 | ThuFeb 12 | 6:00 PM | Doom Movement | Sports | Elston Electric | 1357 N Elston Ave | All Ages | Free | |
 | ThuFeb 12 | 6:00 PM | JADE - THAT'S SHOWBIZ BABY! THE TOUR | Music | Pop | House of Blues Chicago | 329 N Dearborn St | All Ages | Free |
| ThuFeb 12 | 7:00 PM | Hamnet | Art & Theatre | Chicago Shakespeare Theater | 800 East Grand Avenue on Navy Pier | All Ages | Free | |
| ThuFeb 12 | 7:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
 | ThuFeb 12 | 7:00 PM | Disney On Ice presents Jump In! | Family | Ice Shows | United Center | 1901 W Madison | All Ages | Free |
 | ThuFeb 12 | 7:00 PM | Crying at the Shed - Day 1 | Music | The Salt Shed Indoors (Shed) | 1357 N Elston Ave | All Ages | Free | |
| ThuFeb 12 | 7:00 PM | The Outsiders (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| ThuFeb 12 | 7:00 PM | Nightcap Lecture Series: A Conversation ... | Music | Three Top Lounge | 1357 N Elston Avenue | All Ages | Free | |
 | ThuFeb 12 | 7:00 PM | Crying at The Shed - Festival Pass | Fairs & Festivals | The Salt Shed Indoors (Shed) | 1357 N Elston Ave | All Ages | Free | |
| ThuFeb 12 | 7:00 PM | Bernadette: The Musical | Art & Theatre | Athenaeum Theatre | 2936 N. Southport Ave. | All Ages | Free | |
 | ThuFeb 12 | 7:30 PM | Jaap van Zweden, Himari & Mozart Jupiter | Music | Classical | Orchestra Hall - IL | 220 S. Michigan Ave. | All Ages | Free |
| ThuFeb 12 | 8:00 PM | Kanii | Music | Subterranean | 2011 North Ave | All Ages | Free | |
 | ThuFeb 12 | 8:00 PM | Summer Salt w/ Boyscott | Music | Other | Metro | 3730 N. Clark St. | All Ages | Free |
| ThuFeb 12 | 8:00 PM | Sebastian Rider, Fernando Jones & My Ban... | Music | Blues | Reggies Music Joint | 2105 South State Street | All Ages | Free |
 | ThuFeb 12 | 8:00 PM | People Brothers Band | Music | Rock | Garcia's Chicago | 1001 W Washington Blvd | All Ages | Free |
 | ThuFeb 12 | 8:00 PM | Weval: CHOROPHOBIA - Album Release Tour | Music | Pop | Outset | 1675 N Elston Ave | All Ages | Free |
 | ThuFeb 12 | 8:00 PM | Rani, Bread On Fork, Luscia Jane | Music | Pop | Reggies Bananna's Shack | 2105 South State Street | All Ages | Free |
 | ThuFeb 12 | 9:00 PM | *SOLD OUT* The Rural Alberta Advantage | Music | Alternative | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
| FriFeb 13 | 10:30 AM | Disney On Ice presents Jump In! | Family | Ice Shows | United Center | 1901 W Madison | All Ages | Free |
| FriFeb 13 | 5:00 PM | Crying at The Shed - Day 2 (Beginners, Y... | Music | The Salt Shed Indoors (Shed) | 1357 N Elston Ave | All Ages | Free | |
 | FriFeb 13 | 5:30 PM | Hard Country Honky Tonk with The Hoyle B... | Music | Country | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
 | FriFeb 13 | 6:00 PM | ChiTown Drive-In Presents -The Lady and ... | Family | ChiTown Movies | 2343 S Throop St | All Ages | Free One ticket per vehicle for up to 6 adults. All sp... | |
| FriFeb 13 | 6:00 PM | Chicago Public League | Sports | Basketball | Credit Union 1 Arena at UIC | 525 South Racine | All Ages | Free |
| FriFeb 13 | 7:00 PM | Mike Wheeler Blues Band/Nora Jean Wallac... | Music | Blues | Kingston Mines - Chicago Blues Center | 2548 North Halsted | All Ages | Free |
 | FriFeb 13 | 7:00 PM | OG Stevo with Special Guests | Music | Hip-Hop/Rap | Foundation Room at House of Blues Chicag... | 329 N Dearborn St | All Ages | Free |
| FriFeb 13 | 7:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
| FriFeb 13 | 7:00 PM | Bernadette: The Musical | Art & Theatre | Athenaeum Theatre | 2936 N. Southport Ave. | All Ages | Free | |
 | FriFeb 13 | 7:00 PM | Motion City Soundtrack w/ Say Anything | Music | Alternative | Riviera Theatre- IL | 4750 N. Broadway | All Ages | Free |
| FriFeb 13 | 7:00 PM | Disney On Ice presents Jump In! | Family | Ice Shows | United Center | 1901 W Madison | All Ages | Free |
| FriFeb 13 | 7:00 PM | UpDating (18 and Over) | Music | Vic Theater | 3145 N Sheffield Ave | All Ages | Free | |
 | FriFeb 13 | 7:00 PM | Justin Furstenfeld | Music | Rock | House of Blues Chicago | 329 N Dearborn St | All Ages | Free |
| FriFeb 13 | 7:00 PM | Cosi Fan Tutte | Art & Theatre | Opera | Civic Opera House | 20 N. Wacker Dr. | All Ages | Free |
| FriFeb 13 | 7:00 PM | The Outsiders (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| FriFeb 13 | 7:00 PM | Hamnet | Art & Theatre | Chicago Shakespeare Theater | 800 East Grand Avenue on Navy Pier | All Ages | Free | |
 | FriFeb 13 | 7:30 PM | Jovian Moon, Garm | Music | Jazz | Reggies Bananna's Shack | 2105 South State Street | All Ages | Free |
FriFeb 13 | 7:30 PM | ChiTown Drive-In Presents -10 Things I H... | Art & Theatre | ChiTown Movies | 2343 S Throop St | All Ages | Free One ticket per vehicle for up to 6 adults. All sp... | ||
| FriFeb 13 | 7:30 PM | With Love, Le Bump | Fairs & Festivals | Three Top Lounge | 1357 N Elston Avenue | All Ages | Free | |
 | FriFeb 13 | 8:00 PM | The Heavyweights | Music | Rock | Garcia's Chicago | 1001 W Washington Blvd | All Ages | Free |
 | FriFeb 13 | 8:00 PM | Anime Night | Art & Theatre | Community/Civic | Reggies Rock Club | 2109 South State Street | All Ages | Free |
| FriFeb 13 | 8:00 PM | Iris Blue, Billy Joel Jr., Abel | Music | Rock | Reggies Music Joint | 2105 South State Street | All Ages | Free |
| FriFeb 13 | 8:00 PM | Barn Dance Apocalypse | Music | Thalia Hall | 1807 S Allport St | All Ages | Free | |
 | FriFeb 13 | 8:00 PM | Adam Doleac - Dream House Tour with Made... | Music | Country | Joe's on Weed Street | 940 West Weed St. | All Ages | Free |
 | FriFeb 13 | 8:00 PM | Josh Johnson: The Flowers Tour | Art & Theatre | Comedy | The Chicago Theatre | 175 N State St | All Ages | Free |
| FriFeb 13 | 9:30 PM | Bootleggers | Music | Country | Carol's Pub | 4659 North Clark Street | All Ages | Free |
 | FriFeb 13 | 10:00 PM | Opiuo | Music | Pop | Outset | 1675 N Elston Ave | All Ages | Free |
| FriFeb 13 | 12:00 AM | Loyola Ramblers Mens Basketball vs. St. ... | Sports | Basketball | Gentile Arena | 1032 W Sheridan Rd | All Ages | Free |
| SatFeb 14 | 10:30 AM | Disney On Ice presents Jump In! | Family | Ice Shows | United Center | 1901 W Madison | All Ages | Free |
 | SatFeb 14 | 11:00 AM | Vip Stadium Tour | Sports | Miscellaneous | Soldier Field | 1410 S. Museum Campus Drive | All Ages | Free |
| SatFeb 14 | 12:00 PM | Handmade Market | Fairs & Festivals | Empty Bottle | 1035 N. Western Ave. | All Ages | Free | |
| SatFeb 14 | 1:00 PM | Vip Stadium Tour | Sports | Miscellaneous | Soldier Field | 1410 S. Museum Campus Drive | All Ages | Free |
| SatFeb 14 | 2:00 PM | The Outsiders (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| SatFeb 14 | 2:00 PM | Hamnet | Art & Theatre | Chicago Shakespeare Theater | 800 East Grand Avenue on Navy Pier | All Ages | Free | |
| SatFeb 14 | 2:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
| SatFeb 14 | 2:30 PM | Disney On Ice presents Jump In! | Family | Ice Shows | United Center | 1901 W Madison | All Ages | Free |
 | SatFeb 14 | 2:30 PM | Crying at The Shed - Day 3 (Lady and the... | Art & Theatre | The Salt Shed Indoors (Shed) | 1357 N Elston Ave | All Ages | Free | |
| SatFeb 14 | 5:00 PM | Josh Johnson: The Flowers Tour | Art & Theatre | Comedy | The Chicago Theatre | 175 N State St | All Ages | Free |
| SatFeb 14 | 5:45 PM | ChiTown Drive-In Presents -The Lady and ... | Family | ChiTown Movies | 2343 S Throop St | All Ages | Free One ticket per vehicle for up to 6 adults. All sp... | |
| SatFeb 14 | 6:00 PM | Loyola Ramblers Womens Basketball vs. St... | Sports | Basketball | Gentile Arena | 1032 W Sheridan Rd | All Ages | Free |
| SatFeb 14 | 6:00 PM | Punch Palace | Fairs & Festivals | Punch House | 1227 W 18th St | All Ages | Free | |
| SatFeb 14 | 6:30 PM | The Heavyweights | Music | Rock | Garcia's Chicago | 1001 W Washington Blvd | All Ages | Free |
| SatFeb 14 | 6:30 PM | Disney On Ice presents Jump In! | Family | Ice Shows | United Center | 1901 W Madison | All Ages | Free |
| SatFeb 14 | 7:00 PM | Justin Furstenfeld | Music | Rock | House of Blues Chicago | 329 N Dearborn St | All Ages | Free |
 | SatFeb 14 | 7:00 PM | Valentine's Day Comedy Show | Art & Theatre | Comedy | The Auditorium | 50 E Ida B. Wells Drive | All Ages | Free |
| SatFeb 14 | 7:00 PM | Hamnet | Art & Theatre | Chicago Shakespeare Theater | 800 East Grand Avenue on Navy Pier | All Ages | Free | |
 | SatFeb 14 | 7:00 PM | The Ken Davis Project Ft. Ruth Lindo | Music | R&B | Reggies Bananna's Shack | 2105 South State Street | All Ages | Free |
 | SatFeb 14 | 7:00 PM | 7 Deadly Sins | Art & Theatre | Miscellaneous | Copernicus Center | 5216 W Lawrence Ave | All Ages | Free |
| SatFeb 14 | 7:00 PM | Mike Wheeler Blues Band/Nora Jean Wallac... | Music | Blues | Kingston Mines - Chicago Blues Center | 2548 North Halsted | All Ages | Free |
| SatFeb 14 | 7:30 PM | Jaap van Zweden, Himari & Mozart Jupiter | Music | Classical | Orchestra Hall - IL | 220 S. Michigan Ave. | All Ages | Free |
| SatFeb 14 | 7:30 PM | Salome | Art & Theatre | Performance Art | Civic Opera House | 20 N. Wacker Dr. | All Ages | Free |
| SatFeb 14 | 7:30 PM | The Outsiders (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
SatFeb 14 | 7:30 PM | ChiTown Drive-In Presents -10 Things I H... | Art & Theatre | ChiTown Movies | 2343 S Throop St | All Ages | Free One ticket per vehicle for up to 6 adults. All sp... | ||
| SatFeb 14 | 7:30 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
| SatFeb 14 | 7:30 PM | Bernadette: The Musical | Art & Theatre | Athenaeum Theatre | 2936 N. Southport Ave. | All Ages | Free | |
| SatFeb 14 | 8:00 PM | Josh Johnson: The Flowers Tour | Art & Theatre | Comedy | The Chicago Theatre | 175 N State St | All Ages | Free |
| SatFeb 14 | 8:00 PM | Deraps, Kevin M Buck | Music | Rock | Reggies Music Joint | 2105 South State Street | All Ages | Free |
 | SatFeb 14 | 8:00 PM | The Barr Brothers with Anna Tivel | Music | Folk | Thalia Hall | 1807 S Allport St | All Ages | Free |
 | SatFeb 14 | 8:00 PM | The Koffin Kats, the Last Gang, Crazy & ... | Music | Rock | Reggies Rock Club | 2109 South State Street | All Ages | Free |
| SatFeb 14 | 8:00 PM | One Direction Dance Party x Valentines D... | Music | Rock | Joe's on Weed Street | 940 West Weed St. | All Ages | Free |
| SunFeb 15 | 10:30 AM | Disney On Ice presents Jump In! | Family | Ice Shows | United Center | 1901 W Madison | All Ages | Free |
| SunFeb 15 | 12:00 PM | Fantasy Lunch - Magic The Gathering | Sports | Empty Bottle | 1035 N. Western Ave. | All Ages | Free | |
| SunFeb 15 | 1:00 PM | The Outsiders (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| SunFeb 15 | 1:00 PM | Bernadette: The Musical | Art & Theatre | Athenaeum Theatre | 2936 N. Southport Ave. | All Ages | Free | |
SunFeb 15 | 2:00 PM | UIC Flames Men's Basketball v Illinois S... | Sports | Basketball | Credit Union 1 Arena at UIC | 525 South Racine | All Ages | Free | |
| SunFeb 15 | 2:00 PM | Hamnet | Art & Theatre | Chicago Shakespeare Theater | 800 East Grand Avenue on Navy Pier | All Ages | Free | |
| SunFeb 15 | 2:00 PM | Cosi Fan Tutte | Art & Theatre | Opera | Civic Opera House | 20 N. Wacker Dr. | All Ages | Free |
| SunFeb 15 | 2:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
| SunFeb 15 | 2:30 PM | Disney On Ice presents Jump In! | Family | Ice Shows | United Center | 1901 W Madison | All Ages | Free |
| SunFeb 15 | 3:00 PM | Jaap van Zweden, Himari & Mozart Jupiter | Music | Classical | Orchestra Hall - IL | 220 S. Michigan Ave. | All Ages | Free |
| SunFeb 15 | 5:00 PM | Josh Johnson: The Flowers Tour | Art & Theatre | Comedy | The Chicago Theatre | 175 N State St | All Ages | Free |
 | SunFeb 15 | 5:30 PM | Kingston Mines "Blues Jam" with Mike Whe... | Music | Blues | Kingston Mines - Chicago Blues Center | 2548 North Halsted | All Ages | Free |
 | SunFeb 15 | 6:00 PM | Arkona, Ad Infinitum, Seven Spires, Hels... | Music | Metal | Reggies Rock Club | 2109 South State Street | All Ages | Free |
| SunFeb 15 | 6:00 PM | Sgt. Goof's Lonely Hearts Ball | Music | Other | Bottom Lounge | 1375 W. Lake St | All Ages | Free |
| SunFeb 15 | 6:30 PM | Disney On Ice presents Jump In! | Family | Ice Shows | United Center | 1901 W Madison | All Ages | Free |
| SunFeb 15 | 6:30 PM | The Outsiders (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| SunFeb 15 | 7:00 PM | Mariachi Herencia De Mexico: Homenaje a ... | Music | Other | Thalia Hall | 1807 S Allport St | All Ages | Free |
 | SunFeb 15 | 7:00 PM | Let's Go Girls | Music | Country | Garcia's Chicago | 1001 W Washington Blvd | All Ages | Free |
 | SunFeb 15 | 7:30 PM | YFN Lucci - ALREADY LEGEND. the 2026 tou... | Music | Hip-Hop/Rap | The Salt Shed Indoors (Shed) | 1357 N Elston Ave | All Ages | Free |
 | SunFeb 15 | 8:00 PM | Kristiane | Music | Alternative | Schubas | 3159 N Southport Ave | All Ages | Free |
| SunFeb 15 | 8:00 PM | Josh Johnson: The Flowers Tour | Art & Theatre | Comedy | The Chicago Theatre | 175 N State St | All Ages | Free |
 | SunFeb 15 | 8:00 PM | Anti-Everything, Retrogression, Tongan D... | Music | Metal | Reggies Music Joint | 2105 South State Street | All Ages | Free |
| SunFeb 15 | 8:30 PM | Selector King Tony | Music | Other | Three Top Lounge | 1357 N Elston Avenue | All Ages | Free |
 | SunFeb 15 | 9:00 PM | Center for Native Futures Presents: Blac... | Music | Alternative | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
SunFeb 15 | 12:00 AM | The Chicago Theatre Tour Experience | Art & Theatre | Undefined | The Chicago Theatre Tour Experience | 175 N State St | All Ages | Free | |
| MonFeb 16 | 11:00 AM | Classic Stadium Tour | Sports | Miscellaneous | Soldier Field | 1410 S. Museum Campus Drive | All Ages | Free |
| MonFeb 16 | 12:30 PM | Classic Stadium Tour | Sports | Miscellaneous | Soldier Field | 1410 S. Museum Campus Drive | All Ages | Free |
| MonFeb 16 | 9:00 PM | FREE MONDAY w/ Hannah Sandoz / Giant Pit... | Music | Other | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
| TueFeb 17 | 7:00 PM | The Outsiders (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| TueFeb 17 | 7:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
| TueFeb 17 | 7:00 PM | Grand Kyiv Ballet: Giselle | Art & Theatre | Harris Theater | 205 East Randolph Drive | All Ages | Free | |
| TueFeb 17 | 7:00 PM | Hamnet | Art & Theatre | Chicago Shakespeare Theater | 800 East Grand Avenue on Navy Pier | All Ages | Free | |
| WedFeb 18 | 1:00 PM | Hamnet | Art & Theatre | Chicago Shakespeare Theater | 800 East Grand Avenue on Navy Pier | All Ages | Free | |
| WedFeb 18 | 1:00 PM | The Outsiders (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| WedFeb 18 | 6:00 PM | Loyola Ramblers Womens Basketball vs. Ge... | Sports | Basketball | Gentile Arena | 1032 W Sheridan Rd | All Ages | Free |
| WedFeb 18 | 6:00 PM | Chicago Public League | Sports | Basketball | Credit Union 1 Arena at UIC | 525 South Racine | All Ages | Free |
| WedFeb 18 | 7:00 PM | Bernadette: The Musical | Art & Theatre | Athenaeum Theatre | 2936 N. Southport Ave. | All Ages | Free | |
| WedFeb 18 | 7:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
| WedFeb 18 | 7:00 PM | Hamnet | Art & Theatre | Chicago Shakespeare Theater | 800 East Grand Avenue on Navy Pier | All Ages | Free | |
| WedFeb 18 | 7:00 PM | The Outsiders (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
 | WedFeb 18 | 7:30 PM | Aliejha, Bella Moss, Caro Granner | Music | Folk | Reggies Music Joint | 2105 South State Street | All Ages | Free |
| WedFeb 18 | 8:00 PM | Monolink | Music | Other | Vic Theater | 3145 N Sheffield Ave | All Ages | Free |
 | WedFeb 18 | 8:00 PM | Freya Skye - Stars Align Tour | Music | Pop | The Salt Shed Indoors (Shed) | 1357 N Elston Ave | All Ages | Free |
WedFeb 18 | 8:00 PM | George Porter JR & Runnin' Pardners | Music | R&B | Garcia's Chicago | 1001 W Washington Blvd | All Ages | Free | |
| ThuFeb 19 | 5:30 PM | Three Top Happy Hour | Networking | Three Top Lounge | 1357 N Elston Avenue | All Ages | Free | |
| ThuFeb 19 | 6:00 PM | Judges Joke | Art & Theatre | Bottom Lounge | 1375 W. Lake St | All Ages | Free | |
ThuFeb 19 | 6:00 PM | Chicago Comedy Club | Art & Theatre | Comedy | Foundation Room at House of Blues Chicag... | 329 N Dearborn St | All Ages | Free | |
| ThuFeb 19 | 6:00 PM | Joanna Connor Blues Band/TBD | Music | Blues | Kingston Mines - Chicago Blues Center | 2548 North Halsted | All Ages | Free |
| ThuFeb 19 | 7:00 PM | Hamnet | Art & Theatre | Chicago Shakespeare Theater | 800 East Grand Avenue on Navy Pier | All Ages | Free | |
 | ThuFeb 19 | 7:00 PM | Jim Gaffigan: Everything is Wonderful! | Art & Theatre | Comedy | The Chicago Theatre | 175 N State St | All Ages | Free |
| ThuFeb 19 | 7:00 PM | Bernadette: The Musical | Art & Theatre | Athenaeum Theatre | 2936 N. Southport Ave. | All Ages | Free | |
| ThuFeb 19 | 7:00 PM | The Outsiders (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| ThuFeb 19 | 7:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
ThuFeb 19 | 7:00 PM | Chicago Bulls vs. Toronto Raptors | Sports | Basketball | United Center | 1901 W Madison | All Ages | Free | |
| ThuFeb 19 | 7:30 PM | Makela Conducts Ein Heldenleben | Music | Classical | Orchestra Hall - IL | 220 S. Michigan Ave. | All Ages | Free |
| ThuFeb 19 | 8:00 PM | Lo Essencial, Direccion Contraria, Expoe... | Music | Rock | Reggies Music Joint | 2105 South State Street | All Ages | Free |
| ThuFeb 19 | 8:00 PM | Tyler Halverson - In Defense Of Drinking... | Music | Country | Carol's Pub | 4659 North Clark Street | All Ages | Free |
ThuFeb 19 | 8:00 PM | George Porter JR & Runnin' Pardners | Music | R&B | Garcia's Chicago | 1001 W Washington Blvd | All Ages | Free | |
| ThuFeb 19 | 9:00 PM | DANA / Clickbait / Cel Ray / Bath Drawer... | Music | Rock | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
| FriFeb 20 | 11:00 AM | Classic Stadium Tour | Sports | Miscellaneous | Soldier Field | 1410 S. Museum Campus Drive | All Ages | Free |
| FriFeb 20 | 12:30 PM | Classic Stadium Tour | Sports | Miscellaneous | Soldier Field | 1410 S. Museum Campus Drive | All Ages | Free |
| FriFeb 20 | 5:30 PM | Hard Country Honky Tonk with The Hoyle B... | Music | Country | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
| FriFeb 20 | 6:00 PM | Honey with DJ CashEra | Music | R&B | Three Top Lounge | 1357 N Elston Avenue | All Ages | Free |
| FriFeb 20 | 6:00 PM | Chicago Public League | Sports | Basketball | Credit Union 1 Arena at UIC | 525 South Racine | All Ages | Free |
| FriFeb 20 | 6:30 PM | Next Showcase USA | Music | Other | Foundation Room at House of Blues Chicag... | 329 N Dearborn St | All Ages | Free |
| FriFeb 20 | 7:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
| FriFeb 20 | 7:00 PM | Kickback to Kirkwood- Chicago's Biggest ... | Music | Joe's on Weed Street | 940 West Weed St. | All Ages | Free | |
| FriFeb 20 | 7:00 PM | Joanna Connor Blues Band/Omar Coleman Bl... | Music | Blues | Kingston Mines - Chicago Blues Center | 2548 North Halsted | All Ages | Free |
| FriFeb 20 | 7:00 PM | Jim Gaffigan: Everything is Wonderful! | Art & Theatre | Comedy | The Chicago Theatre | 175 N State St | All Ages | Free |
| FriFeb 20 | 7:00 PM | Bernadette: The Musical | Art & Theatre | Athenaeum Theatre | 2936 N. Southport Ave. | All Ages | Free | |
| FriFeb 20 | 7:00 PM | The Outsiders (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| FriFeb 20 | 7:00 PM | Hamnet | Art & Theatre | Chicago Shakespeare Theater | 800 East Grand Avenue on Navy Pier | All Ages | Free | |
 | FriFeb 20 | 7:30 PM | Ruby w/ Coach House, The Fighting Godot | Music | Alternative | Cubby Bear | 1059 West Addison | All Ages | Free |
 | FriFeb 20 | 7:30 PM | THE LONE BELLOW 2026 TOUR with Fabrizio | Music | Folk | Thalia Hall | 1807 S Allport St | All Ages | Free |
 | FriFeb 20 | 7:30 PM | Rich Brian | Music | Other | Riviera Theatre- IL | 4750 N. Broadway | All Ages | Free |
| FriFeb 20 | 7:30 PM | Makela Conducts Ein Heldenleben | Music | Classical | Orchestra Hall - IL | 220 S. Michigan Ave. | All Ages | Free |
 | FriFeb 20 | 8:00 PM | Schur | Music | Rock | Garcia's Chicago | 1001 W Washington Blvd | All Ages | Free |
| FriFeb 20 | 8:00 PM | Embittered, Ashbringer, Vukari, Motherle... | Music | Metal | Reggies Rock Club | 2109 South State Street | All Ages | Free |
 | FriFeb 20 | 8:00 PM | Wooli | Music | Pop | The Salt Shed Indoors (Shed) | 1357 N Elston Ave | All Ages | Free |
| FriFeb 20 | 8:30 PM | You Died, James the Boneless, Black Cat ... | Music | Rock | Reggies Music Joint | 2105 South State Street | All Ages | Free |
| FriFeb 20 | 8:30 PM | Sonus Umbra, Kingery | Music | Rock | Reggies Bananna's Shack | 2105 South State Street | All Ages | Free |
 | FriFeb 20 | 8:30 PM | Justin Bieber Night: Presented by Stan S... | Music | Pop | House of Blues Chicago | 329 N Dearborn St | All Ages | Free |
| FriFeb 20 | 9:30 PM | Blue Rose | Music | Rock | Carol's Pub | 4659 North Clark Street | All Ages | Free |
 | SatFeb 21 | 1:00 PM | Music Frozen Dancing with Los Thuthanaka... | Music | Other | Outside the Empty Bottle | Western Ave & Cortez | All Ages | Free |
| SatFeb 21 | 2:00 PM | The Outsiders (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
SatFeb 21 | 2:00 PM | UIC Flames Men's Basketball v Valparaiso | Sports | Basketball | Credit Union 1 Arena at UIC | 525 South Racine | All Ages | Free | |
| SatFeb 21 | 2:00 PM | Bernadette: The Musical | Art & Theatre | Athenaeum Theatre | 2936 N. Southport Ave. | All Ages | Free | |
| SatFeb 21 | 2:00 PM | Hamnet | Art & Theatre | Chicago Shakespeare Theater | 800 East Grand Avenue on Navy Pier | All Ages | Free |