| Date | Time | Event Name | Type | Genre | Venue | Address | Age | Price | |
|---|---|---|---|---|---|---|---|---|---|
 | MonJan 19 | 7:30 PM | Chicago Blackhawks vs. Winnipeg Jets | Sports | Hockey | United Center | 1901 W Madison | All Ages | Free |
 | MonJan 19 | 9:00 PM | Ordinary Peepholes : Beanie Baby Teletho... | Fairs & Festivals | Empty Bottle | 1035 N. Western Ave. | All Ages | Free | |
 | TueJan 20 | 7:00 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
TueJan 20 | 7:00 PM | Chicago Bulls vs. LA Clippers | Sports | Basketball | United Center | 1901 W Madison | All Ages | Free | |
 | TueJan 20 | 7:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
TueJan 20 | 7:00 PM | UIC Flames Men's Basketball v Evansville | Sports | Basketball | Credit Union 1 Arena at UIC | 525 South Racine | All Ages | Free | |
 | TueJan 20 | 9:00 PM | Tarta Relena + Meara O’Reilly’s Hockets... | Music | Folk | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
| WedJan 21 | 1:00 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
 | WedJan 21 | 6:00 PM | Doom Movement Yoga Practice | Sports | Elston Electric | 1357 N Elston Ave | All Ages | Free | |
 | WedJan 21 | 6:00 PM | Loyola Ramblers Womens Basketball vs. La... | Sports | Basketball | Gentile Arena | 1032 W Sheridan Rd | All Ages | Free |
| WedJan 21 | 6:30 PM | Pyre Blue w/ Funk Master Jones, Cameron ... | Music | Alternative | Cubby Bear | 1059 West Addison | All Ages | Free |
| WedJan 21 | 7:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
| WedJan 21 | 7:00 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
 | WedJan 21 | 7:00 PM | glaive w/ Kurtains | Music | Other | Metro | 3730 N. Clark St. | All Ages | Free |
 | WedJan 21 | 7:30 PM | Snow Strippers w/ EERA | Music | Riviera Theatre- IL | 4750 N. Broadway | All Ages | Free | |
 | WedJan 21 | 8:00 PM | M'reld Green Live At Reggies | Art & Theatre | Miscellaneous Theatre | Reggies Bananna's Shack | 2105 South State Street | All Ages | Free |
 | WedJan 21 | 8:00 PM | *SOLD OUT* Jonah Kagen with Vincent Lima | Music | Pop | Thalia Hall | 1807 S Allport St | All Ages | Free |
 | WedJan 21 | 9:00 PM | Various Distractions with DON (Live) / D... | Music | Other | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
 | ThuJan 22 | 5:30 PM | Three Top Happy Hour | Fairs & Festivals | Three Top Lounge | 1357 N Elston Avenue | All Ages | Free | |
 | ThuJan 22 | 6:00 PM | Rico McFarland Band/Studebaker John Blue... | Music | Blues | Kingston Mines - Chicago Blues Center | 2548 North Halsted | All Ages | Free |
| ThuJan 22 | 7:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
 | ThuJan 22 | 7:00 PM | Janeff the Poet | Music | R&B | Reggies Bananna's Shack | 2105 South State Street | All Ages | Free |
 | ThuJan 22 | 7:00 PM | UIC Flames Women's Basketball v Illinois... | Sports | Basketball | Credit Union 1 Arena at UIC | 525 South Racine | All Ages | Free |
| ThuJan 22 | 7:00 PM | Nightcap Lecture Series: Tina Post on Co... | Art & Theatre | Three Top Lounge | 1357 N Elston Avenue | All Ages | Free | |
| ThuJan 22 | 7:00 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
 | ThuJan 22 | 7:30 PM | Alenia w/ Rose of Demise, Orinoco | Music | Metal | Cubby Bear | 1059 West Addison | All Ages | Free |
 | ThuJan 22 | 7:30 PM | Loewy, Cheryl Rodey Band, Julia Morrison | Music | Pop | Reggies Music Joint | 2105 South State Street | All Ages | Free |
 | ThuJan 22 | 8:00 PM | The Jack Wharff Band - From The Hills To... | Music | Country | Carol's Pub | 4659 North Clark Street | All Ages | Free |
ThuJan 22 | 8:00 PM | Terrapin Flyer | Music | Rock | Garcia's Chicago | 1001 W Washington Blvd | All Ages | Free | |
 | ThuJan 22 | 8:00 PM | Cate Le Bon with Frances Chang | Music | Folk | Thalia Hall | 1807 S Allport St | All Ages | Free |
| ThuJan 22 | 9:00 PM | Clairice / Sponj / Rich Jones / Oddcoupl... | Music | Other | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
| FriJan 23 | 5:30 PM | Hard Country Honky Tonk with The Hoyle B... | Music | Country | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
| FriJan 23 | 6:00 PM | Chicago Blackhawks vs. Tampa Bay Lightni... | Sports | Hockey | United Center | 1901 W Madison | All Ages | Free |
 | FriJan 23 | 6:00 PM | Club 90s Presents Heated RivalRave | Music | Pop | House of Blues Chicago | 329 N Dearborn St | All Ages | Free |
| FriJan 23 | 7:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
| FriJan 23 | 7:00 PM | Nora Jean Wallace Blues Band/Omar Colema... | Music | Blues | Kingston Mines - Chicago Blues Center | 2548 North Halsted | All Ages | Free |
| FriJan 23 | 7:00 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
 | FriJan 23 | 7:30 PM | Mid-Air, Mateo Suarez & the Public Ear, ... | Music | Other | Reggies Bananna's Shack | 2105 South State Street | All Ages | Free |
 | FriJan 23 | 7:30 PM | The Thanks I Get w/ Hot Alice, SMFC, FOU... | Music | Rock | Cubby Bear | 1059 West Addison | All Ages | Free |
 | FriJan 23 | 8:00 PM | Dry Cleaning with YHWH Nailgun | Music | Alternative | Thalia Hall | 1807 S Allport St | All Ages | Free |
| FriJan 23 | 8:00 PM | The Front Desk with What's Her Face and ... | Music | Alternative | Joe's on Weed Street | 940 West Weed St. | All Ages | Free |
 | FriJan 23 | 8:00 PM | Bad Bad Hats w/ SMUT | Music | Other | Lincoln Hall | 2424 N. Lincoln Ave | All Ages | Free |
| FriJan 23 | 8:00 PM | Dry Cleaning w/ YHWH Nailgun | Music | Other | Thalia Hall | 1807 S Allport Street | All Ages | Free |
FriJan 23 | 8:00 PM | Terrapin Flyer | Music | Rock | Garcia's Chicago | 1001 W Washington Blvd | All Ages | Free | |
| FriJan 23 | 8:30 PM | Duane Powell | Music | Other | Three Top Lounge | 1357 N Elston Avenue | All Ages | Free |
| FriJan 23 | 8:30 PM | Model J, Evening Underground | Music | Rock | Reggies Music Joint | 2105 South State Street | All Ages | Free |
 | FriJan 23 | 9:00 PM | Emo Night Brooklyn | Music | Rock | Bottom Lounge | 1375 W. Lake St | All Ages | Free |
| FriJan 23 | 9:30 PM | Buddy Damen & The Last Call | Music | Country | Carol's Pub | 4659 North Clark Street | All Ages | Free |
 | FriJan 23 | 10:00 PM | Wreckno | Music | Pop | Outset | 1675 N Elston Ave | All Ages | Free |
FriJan 23 | 12:00 AM | The Chicago Theatre Tour Experience | Art & Theatre | Undefined | The Chicago Theatre Tour Experience | 175 N State St | All Ages | Free | |
 | SatJan 24 | 11:00 AM | Classic Stadium Tour | Sports | Miscellaneous | Soldier Field | 1410 S. Museum Campus Drive | All Ages | Free |
| SatJan 24 | 12:30 PM | Classic Stadium Tour | Sports | Miscellaneous | Soldier Field | 1410 S. Museum Campus Drive | All Ages | Free |
| SatJan 24 | 1:00 PM | Loyola Ramblers Mens Basketball vs. Duqu... | Sports | Basketball | Gentile Arena | 1032 W Sheridan Rd | All Ages | Free |
| SatJan 24 | 2:00 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| SatJan 24 | 2:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
| SatJan 24 | 2:00 PM | Classic Stadium Tour | Sports | Miscellaneous | Soldier Field | 1410 S. Museum Campus Drive | All Ages | Free |
| SatJan 24 | 6:30 PM | Electric Cars w/ Tragic Blonde Vacation | Music | Alternative | Cubby Bear | 1059 West Addison | All Ages | Free |
| SatJan 24 | 7:00 PM | Nacho Redondo | Music | Park West | 322 W. Armitage | All Ages | Free | |
SatJan 24 | 7:00 PM | Chicago Bulls vs. Boston Celtics | Sports | Basketball | United Center | 1901 W Madison | All Ages | Free | |
 | SatJan 24 | 7:00 PM | La Santa Cecilia | Music | Latin | House of Blues Chicago | 329 N Dearborn St | All Ages | Free |
| SatJan 24 | 7:00 PM | Nora Jean Wallace Blues Band/Omar Colema... | Music | Blues | Kingston Mines - Chicago Blues Center | 2548 North Halsted | All Ages | Free |
 | SatJan 24 | 7:30 PM | Martha Graham Dance Company | Art & Theatre | Auditorium Theatre - IL | 50 East Ida B. Wells Drive | All Ages | Free | |
| SatJan 24 | 7:30 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| SatJan 24 | 7:30 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
SatJan 24 | 8:00 PM | Terrapin Flyer | Music | Rock | Garcia's Chicago | 1001 W Washington Blvd | All Ages | Free | |
 | SatJan 24 | 8:00 PM | DRAMA presented by Jack Daniel's | Music | R&B | The Salt Shed Indoors (Shed) | 1357 N Elston Ave | All Ages | Free |
| SatJan 24 | 8:30 PM | The Front Desk, Cat Merkle, Surf Cowboy | Music | Rock | Reggies Music Joint | 2105 South State Street | All Ages | Free |
 | SatJan 24 | 9:00 PM | Fox Stevenson: Sunk Cost Fallacy Tour | Music | Dance/Electronic | Bottom Lounge | 1375 W. Lake St | All Ages | Free |
 | SatJan 24 | 9:00 PM | Ground Control Touring Presents: 4th Ann... | Music | Other | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
| SatJan 24 | 9:30 PM | Frank Martin Busch and the Names | Music | Country | Carol's Pub | 4659 North Clark Street | All Ages | Free |
 | SatJan 24 | 12:00 AM | DePaul Blue Demons Mens Basketball vs. S... | Sports | Basketball | Wintrust Arena | 200 E Cermak Road, Chicago, IL 60616 | All Ages | Free |
| SunJan 25 | 12:00 PM | Art ETC club presents: Harrison Wyrick a... | Art & Theatre | Empty Bottle | 1035 N. Western Ave. | All Ages | Free | |
| SunJan 25 | 1:00 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| SunJan 25 | 2:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
 | SunJan 25 | 2:00 PM | Salome | Art & Theatre | Performance Art | Civic Opera House | 20 N. Wacker Dr. | All Ages | Free |
 | SunJan 25 | 2:00 PM | DePaul Blue Demons Womens Basketball vs.... | Sports | Basketball | Wintrust Arena | 200 E Cermak Road, Chicago, IL 60616 | All Ages | Free |
 | SunJan 25 | 3:00 PM | Kirill Gerstein | Music | Other | Orchestra Hall - IL | 220 S. Michigan Ave. | All Ages | Free |
| SunJan 25 | 5:00 PM | Empty Bottle Record Fair | Music | Other | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
| SunJan 25 | 5:30 PM | Don Was and the Pan-Detroit Ensemble | Music | R&B | Garcia's Chicago | 1001 W Washington Blvd | All Ages | Free |
| SunJan 25 | 5:30 PM | Kingston Mines "Blues Jam" with Mike Whe... | Music | Blues | Kingston Mines - Chicago Blues Center | 2548 North Halsted | All Ages | Free |
| SunJan 25 | 6:00 PM | Chicago Blackhawks vs. Florida Panthers | Sports | Hockey | United Center | 1901 W Madison | All Ages | Free |
| SunJan 25 | 6:30 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
| SunJan 25 | 7:00 PM | Jennette McCurdy | Art & Theatre | Athenaeum Theatre | 2936 N. Southport Ave. | All Ages | Free | |
| SunJan 25 | 7:30 PM | Ashlyn Sisco, Alicia Maka, Nahaar & Char | Music | Pop | Reggies Music Joint | 2105 South State Street | All Ages | Free |
 | SunJan 25 | 8:00 PM | shame with GHOSTWOMAN | Music | Alternative | Thalia Hall | 1807 S Allport St | All Ages | Free |
| SunJan 25 | 8:00 PM | Don Was and the Pan-Detroit Ensemble | Music | R&B | Garcia's Chicago | 1001 W Washington Blvd | All Ages | Free |
SunJan 25 | 12:00 AM | The Chicago Theatre Tour Experience | Art & Theatre | Undefined | The Chicago Theatre Tour Experience | 175 N State St | All Ages | Free | |
| MonJan 26 | 11:00 AM | Classic Stadium Tour | Sports | Miscellaneous | Soldier Field | 1410 S. Museum Campus Drive | All Ages | Free |
| MonJan 26 | 1:00 PM | Classic Stadium Tour | Sports | Miscellaneous | Soldier Field | 1410 S. Museum Campus Drive | All Ages | Free |
MonJan 26 | 7:00 PM | Chicago Bulls vs. Los Angeles Lakers | Sports | Basketball | United Center | 1901 W Madison | All Ages | Free | |
| MonJan 26 | 9:00 PM | FREE MONDAY w/ ABOLISHVICTORY! (Album Re... | Music | Other | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
| TueJan 27 | 7:00 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| TueJan 27 | 7:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
 | TueJan 27 | 7:00 PM | Stereophonic (Chicago) | Art & Theatre | Theatre | CIBC Theatre | 18 West Monroe | All Ages | Free |
TueJan 27 | 7:00 PM | UIC Flames Men's Basketball v Indiana St... | Sports | Basketball | Credit Union 1 Arena at UIC | 525 South Racine | All Ages | Free | |
| TueJan 27 | 9:00 PM | Groovy Magic (Record Release) / Dreamgoa... | Music | Other | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
| TueJan 27 | 12:00 AM | Loyola Ramblers Mens Basketball vs. St. ... | Sports | Basketball | Gentile Arena | 1032 W Sheridan Rd | All Ages | Free |
| WedJan 28 | 1:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
| WedJan 28 | 1:00 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
 | WedJan 28 | 6:00 PM | Doom Movement Yoga Practice | Sports | Elston Electric | 1357 N Elston Ave | All Ages | Free | |
| WedJan 28 | 7:00 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| WedJan 28 | 7:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
| WedJan 28 | 7:00 PM | Stereophonic (Chicago) | Art & Theatre | Theatre | CIBC Theatre | 18 West Monroe | All Ages | Free |
| WedJan 28 | 9:00 PM | Bird Law / Abuse Repression / Perfect / ... | Music | Other | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
| ThuJan 29 | 5:30 PM | Three Top Happy Hour | Networking | Three Top Lounge | 1357 N Elston Avenue | All Ages | Free | |
| ThuJan 29 | 6:00 PM | Mike Wheeler Blues Band/Omar Coleman Blu... | Music | Blues | Kingston Mines - Chicago Blues Center | 2548 North Halsted | All Ages | Free |
ThuJan 29 | 6:00 PM | Chicago Comedy Club | Art & Theatre | Comedy | Foundation Room at House of Blues Chicag... | 329 N Dearborn St | All Ages | Free | |
| ThuJan 29 | 7:00 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| ThuJan 29 | 7:00 PM | Stereophonic (Chicago) | Art & Theatre | Theatre | CIBC Theatre | 18 West Monroe | All Ages | Free |
| ThuJan 29 | 7:00 PM | Salome | Art & Theatre | Performance Art | Civic Opera House | 20 N. Wacker Dr. | All Ages | Free |
| ThuJan 29 | 7:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
 | ThuJan 29 | 7:30 PM | Salonen, Trifonov and Beethoven | Music | Classical | Orchestra Hall - IL | 220 S. Michigan Ave. | All Ages | Free |
 | ThuJan 29 | 8:00 PM | Jim Ryan's Classic Albums Night: Full Al... | Music | Rock | Reggies Music Joint | 2105 South State Street | All Ages | Free |
 | ThuJan 29 | 8:00 PM | Reprise | Music | Other | Garcia's Chicago | 1001 W Washington Blvd | All Ages | Free |
| ThuJan 29 | 9:00 PM | Friendship / Natalie Jane Hill / Krill 2... | Music | Other | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
| FriJan 30 | 11:00 AM | Vip Stadium Tour | Sports | Miscellaneous | Soldier Field | 1410 S. Museum Campus Drive | All Ages | Free |
| FriJan 30 | 1:00 PM | Vip Stadium Tour | Sports | Miscellaneous | Soldier Field | 1410 S. Museum Campus Drive | All Ages | Free |
| FriJan 30 | 5:30 PM | Hard Country Honky Tonk with The Hoyle B... | Music | Country | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
| FriJan 30 | 6:30 PM | Fun To Say w/ Blue Ether, Lex Alley Proj... | Music | Alternative | Cubby Bear | 1059 West Addison | All Ages | Free |
| FriJan 30 | 7:00 PM | Toronzo Cannon Blues Band/Sheryl Youngbl... | Music | Blues | Kingston Mines - Chicago Blues Center | 2548 North Halsted | All Ages | Free |
 | FriJan 30 | 7:00 PM | Rave Jesus - I Met God on the Dancefloo... | Music | Pop | Outset | 1675 N Elston Ave | All Ages | Free |
| FriJan 30 | 7:00 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
FriJan 30 | 7:00 PM | Jessie J - No Secrets Tour | Music | Pop | House of Blues Chicago | 329 N Dearborn St | All Ages | Free | |
| FriJan 30 | 7:00 PM | Stereophonic (Chicago) | Art & Theatre | Theatre | CIBC Theatre | 18 West Monroe | All Ages | Free |
 | FriJan 30 | 7:00 PM | The Infamous Stringdusters with Mountain... | Music | Country | Thalia Hall | 1807 S Allport St | All Ages | Free |
| FriJan 30 | 7:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
| FriJan 30 | 7:30 PM | Jack Riedy and The Dealbreakers w/ Kicke... | Music | Alternative | Cubby Bear | 1059 West Addison | All Ages | Free |
 | FriJan 30 | 7:30 PM | Dean Lewis w/ Matt Hansen | Music | Other | Riviera Theatre- IL | 4750 N. Broadway | All Ages | Free |
| FriJan 30 | 7:30 PM | Chicago Blackhawks vs. Columbus Blue Jac... | Sports | Hockey | United Center | 1901 W Madison | All Ages | Free |
| FriJan 30 | 7:30 PM | Salonen, Trifonov and Beethoven | Music | Classical | Orchestra Hall - IL | 220 S. Michigan Ave. | All Ages | Free |
| FriJan 30 | 8:00 PM | Reprise | Music | Other | Garcia's Chicago | 1001 W Washington Blvd | All Ages | Free |
| FriJan 30 | 8:00 PM | The Serpents Tour Starring Nymphia Wind ... | Music | Vic Theater | 3145 N Sheffield Ave | All Ages | Free | |
 | FriJan 30 | 8:00 PM | House of Burlesque | Art & Theatre | Miscellaneous Theatre | Foundation Room at House of Blues Chicag... | 329 N Dearborn St | All Ages | Free |
 | FriJan 30 | 8:00 PM | The Community Crossover: LATINX x BOLLYW... | Music | Three Top Lounge | 1357 N Elston Avenue | All Ages | Free | |
 | FriJan 30 | 8:00 PM | 1oneam | Music | Hip-Hop/Rap | Reggie's Rock Club | 2105 South State Street | All Ages | Free |
| FriJan 30 | 8:00 PM | Grave Love | Music | Alternative | Bottom Lounge | 1375 W. Lake St | All Ages | Free |
| FriJan 30 | 9:00 PM | Sparkle Carcass and Brandon Good | Music | Country | Carol's Pub | 4659 North Clark Street | All Ages | Free |
| FriJan 30 | 9:00 PM | EMPTY BOTTLE KARAOKE | Music | Other | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
 | FriJan 30 | 9:00 PM | The Toasters - 45 Years of Ska | Music | Rock | Reggies Music Joint | 2105 South State Street | All Ages | Free |
FriJan 30 | 12:00 AM | The Chicago Theatre Tour Experience | Art & Theatre | Undefined | The Chicago Theatre Tour Experience | 175 N State St | All Ages | Free | |
 | SatJan 31 | 10:00 AM | Once Upon a Symphony: The Ugly Duckling | Music | Other | Symphony Center-IL | 220 S. Michigan Ave., Chicago, IL | All Ages | Free |
| SatJan 31 | 11:45 AM | Once Upon a Symphony: The Ugly Duckling | Music | Other | Symphony Center-IL | 220 S. Michigan Ave., Chicago, IL | All Ages | Free |
| SatJan 31 | 2:00 PM | Stereophonic (Chicago) | Art & Theatre | Theatre | CIBC Theatre | 18 West Monroe | All Ages | Free |
| SatJan 31 | 2:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
| SatJan 31 | 2:00 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| SatJan 31 | 2:00 PM | UIC Flames Women's Basketball v Valparai... | Sports | Basketball | Credit Union 1 Arena at UIC | 525 South Racine | All Ages | Free |
| SatJan 31 | 2:00 PM | Loyola Ramblers Womens Basketball vs. St... | Sports | Basketball | Gentile Arena | 1032 W Sheridan Rd | All Ages | Free |
| SatJan 31 | 6:30 PM | Intro to Embroidery - Valentine's Day Fl... | Art & Theatre | Tack Room | 1227 W 18th St. | All Ages | Free | |
 | SatJan 31 | 7:00 PM | Kathleen Madigan: The Day Drinking Tour | Art & Theatre | Comedy | The Chicago Theatre | 175 N State St | All Ages | Free |
| SatJan 31 | 7:00 PM | Toronzo Cannon Blues Band/Sheryl Youngbl... | Music | Blues | Kingston Mines - Chicago Blues Center | 2548 North Halsted | All Ages | Free |
| SatJan 31 | 7:30 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
 | SatJan 31 | 7:30 PM | Atmosphere w/ Sage Francis, R.A. the Rug... | Music | Hip-Hop/Rap | The Salt Shed Indoors (Shed) | 1357 N Elston Ave | All Ages | Free |
| SatJan 31 | 7:30 PM | Salonen, Trifonov and Beethoven | Music | Classical | Orchestra Hall - IL | 220 S. Michigan Ave. | All Ages | Free |
| SatJan 31 | 7:30 PM | Stereophonic (Chicago) | Art & Theatre | Theatre | CIBC Theatre | 18 West Monroe | All Ages | Free |
 | SatJan 31 | 7:30 PM | Cristela Alonzo | Art & Theatre | Miscellaneous | Vic Theater | 3145 N Sheffield Ave | All Ages | Free |
| SatJan 31 | 7:30 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| SatJan 31 | 8:00 PM | Hank Ruff | Music | Country | Joe's on Weed Street | 940 West Weed St. | All Ages | Free |
 | SatJan 31 | 8:00 PM | Big Richard | Music | Country | Garcia's Chicago | 1001 W Washington Blvd | All Ages | Free |
 | SatJan 31 | 8:01 PM | David Spade (16 and Over) | Art & Theatre | Riviera Theatre- IL | 4750 N. Broadway | All Ages | Free | |
| SatJan 31 | 8:30 PM | The Fabulous Cowboys, Hawk and the Talon... | Music | Blues | Reggies Bananna's Shack | 2105 South State Street | All Ages | Free |
| SatJan 31 | 9:00 PM | House Calls 'In the Round' | Music | Other | Thalia Hall | 1807 S Allport St | All Ages | Free |
 | SatJan 31 | 9:00 PM | Fromthe108 - 108day Live! | Sports | Baseball | Reggie's Rock Club | 2105 South State Street | All Ages | Free |
 | SatJan 31 | 9:00 PM | Carrie Nation and the Speakeasy, Royal S... | Music | Country | Reggies Music Joint | 2105 South State Street | All Ages | Free |
| SunFeb 1 | 1:00 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| SunFeb 1 | 1:00 PM | Stereophonic (Chicago) | Art & Theatre | Theatre | CIBC Theatre | 18 West Monroe | All Ages | Free |
 | SunFeb 1 | 2:00 PM | El Temach | Art & Theatre | Theatre | House of Blues Chicago | 329 N Dearborn St | All Ages | Free |
 | SunFeb 1 | 2:00 PM | Cosi Fan Tutte | Art & Theatre | Opera | Civic Opera House | 20 N. Wacker Dr. | All Ages | Free |
| SunFeb 1 | 2:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
| SunFeb 1 | 3:00 PM | Salonen, Trifonov and Beethoven | Music | Classical | Orchestra Hall - IL | 220 S. Michigan Ave. | All Ages | Free |
| SunFeb 1 | 4:00 PM | St. Jams Charity Concert Benefiting Sara... | Music | Other | Carol's Pub | 4659 North Clark Street | All Ages | Free |
| SunFeb 1 | 5:30 PM | Kingston Mines "Blues Jam" with Mike Whe... | Music | Blues | Kingston Mines - Chicago Blues Center | 2548 North Halsted | All Ages | Free |
| SunFeb 1 | 6:00 PM | El Temach | Art & Theatre | Theatre | House of Blues Chicago | 329 N Dearborn St | All Ages | Free |
| SunFeb 1 | 6:30 PM | Stereophonic (Chicago) | Art & Theatre | Theatre | CIBC Theatre | 18 West Monroe | All Ages | Free |
| SunFeb 1 | 8:00 PM | John Inghram Band, Act Casual | Music | Rock | Reggies Music Joint | 2105 South State Street | All Ages | Free |
 | SunFeb 1 | 9:00 PM | Jason Vest, James Fisher Jr., Tina Youkh... | Art & Theatre | Comedy | Reggies Bananna's Shack | 2105 South State Street | All Ages | Free |
 | SunFeb 1 | 9:00 PM | GCO Test 1 - Not All-in | Music | Pop | Soldier Field | 1410 S. Museum Campus Drive | All Ages | Free |
SunFeb 1 | 12:00 AM | The Chicago Theatre Tour Experience | Art & Theatre | Undefined | The Chicago Theatre Tour Experience | 175 N State St | All Ages | Free | |
| MonFeb 2 | 7:30 PM | Chicago Blackhawks vs. San Jose Sharks | Sports | Hockey | United Center | 1901 W Madison | All Ages | Free |
| MonFeb 2 | 9:00 PM | FREE MONDAY w/ Doom Flower / Surgery Boy... | Music | Other | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
| TueFeb 3 | 7:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
| TueFeb 3 | 7:00 PM | Stereophonic (Chicago) | Art & Theatre | Theatre | CIBC Theatre | 18 West Monroe | All Ages | Free |
| TueFeb 3 | 7:00 PM | Loyola Ramblers Mens Basketball vs. LaSa... | Sports | Basketball | Gentile Arena | 1032 W Sheridan Rd | All Ages | Free |
| TueFeb 3 | 7:00 PM | Salome | Art & Theatre | Performance Art | Civic Opera House | 20 N. Wacker Dr. | All Ages | Free |
 | TueFeb 3 | 7:30 PM | Del Water Gap | Music | Other | Riviera Theatre- IL | 4750 N. Broadway | All Ages | Free |
 | TueFeb 3 | 8:00 PM | Caught On Cline, the Masters Collection | Music | Jazz | Reggies Music Joint | 2105 South State Street | All Ages | Free |
| TueFeb 3 | 12:00 AM | DePaul Blue Demons Mens Basketball vs. S... | Sports | Basketball | Wintrust Arena | 200 E Cermak Road, Chicago, IL 60616 | All Ages | Free |
| WedFeb 4 | 1:00 PM | Stereophonic (Chicago) | Art & Theatre | Theatre | CIBC Theatre | 18 West Monroe | All Ages | Free |
| WedFeb 4 | 1:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
| WedFeb 4 | 2:00 PM | Cosi Fan Tutte | Art & Theatre | Opera | Civic Opera House | 20 N. Wacker Dr. | All Ages | Free |
| WedFeb 4 | 7:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
| WedFeb 4 | 7:00 PM | DePaul Blue Demons Womens Basketball vs.... | Sports | Basketball | Wintrust Arena | 200 E Cermak Road, Chicago, IL 60616 | All Ages | Free |
| WedFeb 4 | 7:00 PM | Stereophonic (Chicago) | Art & Theatre | Theatre | CIBC Theatre | 18 West Monroe | All Ages | Free |
| WedFeb 4 | 8:00 PM | Kayzone, Dog.eat.dog, Danielle Crim | Music | Pop | Reggies Music Joint | 2105 South State Street | All Ages | Free |
 | WedFeb 4 | 8:00 PM | New Edition: The New Edition Way Tour | Music | R&B | United Center | 1901 W Madison | All Ages | Free |
 | WedFeb 4 | 9:00 PM | *SOLD OUT* Agriculture / Knoll / Drowse | Music | Metal | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
 | ThuFeb 5 | 6:00 PM | TBD/TBD | Music | Blues | Kingston Mines - Chicago Blues Center | 2548 North Halsted | All Ages | Free |
ThuFeb 5 | 6:00 PM | Chicago Comedy Club | Art & Theatre | Comedy | Foundation Room at House of Blues Chicag... | 329 N Dearborn St | All Ages | Free | |
| ThuFeb 5 | 7:00 PM | Eureka Day (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
 | ThuFeb 5 | 7:00 PM | River West Boxing Club Presents: Fight N... | Sports | Boxing | Joe's on Weed Street | 940 West Weed St. | All Ages | Free |
| ThuFeb 5 | 7:00 PM | UIC Flames Women's Basketball v Southern... | Sports | Basketball | Credit Union 1 Arena at UIC | 525 South Racine | All Ages | Free |