| Date | Time | Event Name | Type | Genre | Venue | Address | Age | Price | |
|---|---|---|---|---|---|---|---|---|---|
 | SunDec 21 | 10:00 AM | World Famous Gospel Brunch at House of B... | Music | Religious | House of Blues Chicago | 329 N Dearborn St | All Ages | Free |
 | SunDec 21 | 12:00 PM | 'Twas the Night Before... by Cirque du S... | Art & Theatre | Circus & Specialty Acts | The Chicago Theatre | 175 N State St | All Ages | Free |
 | SunDec 21 | 12:00 PM | Y'all's Brunch | Fairs & Festivals | Carol's Pub | 4659 North Clark Street | All Ages | Free | |
| SunDec 21 | 12:30 PM | World Famous Gospel Brunch at House of B... | Music | Religious | House of Blues Chicago | 329 N Dearborn St | All Ages | Free |
 | SunDec 21 | 1:00 PM | Merry, Merry Chicago! w/ Chicago Symphon... | Music | Orchestra Hall - IL | 220 S. Michigan Ave. | All Ages | Free | |
| SunDec 21 | 1:00 PM | Ballet Chicago w/ The Nutcracker | Art & Theatre | Harris Theater | 205 East Randolph Drive | All Ages | Free | |
 | SunDec 21 | 1:00 PM | Joffrey Ballet presents The Nutcracker | Art & Theatre | Civic Opera House | 20 N. Wacker Dr. | All Ages | Free | |
 | SunDec 21 | 1:00 PM | Christmas With C.S. Lewis (Chicago) | Art & Theatre | Theatre | Broadway Playhouse at Water Tower Place | 175 E. Chestnut St | All Ages | Free |
 | SunDec 21 | 1:00 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| SunDec 21 | 1:30 PM | Diva Royale Drag Queen Show - 21+ | Art & Theatre | Primary Night Club | 5 W Division St | All Ages | Free | |
| SunDec 21 | 2:00 PM | A Black Ensemble Holiday Spectacular | Art & Theatre | Black Ensemble Theater | 4520 N Beacon | All Ages | Free | |
 | SunDec 21 | 2:00 PM | Much Ado About Nothing | Art & Theatre | Performance Art | Chicago Shakespeare Theater | 800 East Grand Avenue on Navy Pier | All Ages | Free |
| SunDec 21 | 3:00 PM | 'Twas the Night Before... by Cirque du S... | Art & Theatre | Circus & Specialty Acts | The Chicago Theatre | 175 N State St | All Ages | Free |
 | SunDec 21 | 3:30 PM | DePaul Blue Demons Mens Basketball vs. U... | Sports | Basketball | Wintrust Arena | 200 E Cermak Road, Chicago, IL 60616 | All Ages | Free |
 | SunDec 21 | 4:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| SunDec 21 | 4:30 PM | Merry, Merry Chicago! w/ Chicago Symphon... | Music | Orchestra Hall - IL | 220 S. Michigan Ave. | All Ages | Free | |
| SunDec 21 | 5:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
 | SunDec 21 | 5:00 PM | Drunk Shakespeare - 21+ | Art & Theatre | Miscellaneous | The Lion Theatre | 182 N Wabash Ave | All Ages | Free |
| SunDec 21 | 5:00 PM | Ballet Chicago: The Nutcracker (Sensory ... | Art & Theatre | Harris Theater | 205 East Randolph Drive | All Ages | Free | |
| SunDec 21 | 5:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
 | SunDec 21 | 5:30 PM | Closed for Christmas Holiday | Music | Blues | Kingston Mines - Chicago Blues Center | 2548 North Halsted | All Ages | Free |
| SunDec 21 | 5:40 PM | Light of Christmas Drive Thru | Family | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| SunDec 21 | 6:00 PM | 'Twas the Night Before... by Cirque du S... | Art & Theatre | Circus & Specialty Acts | The Chicago Theatre | 175 N State St | All Ages | Free |
| SunDec 21 | 6:00 PM | Joffrey Ballet presents The Nutcracker | Art & Theatre | Civic Opera House | 20 N. Wacker Dr. | All Ages | Free | |
| SunDec 21 | 6:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| SunDec 21 | 6:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| SunDec 21 | 6:30 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
 | SunDec 21 | 6:30 PM | ChiTown Drive-In Presents - Home Alone | Family | Comedy | ChiTown Movies | 2343 S Throop St | All Ages | Free One ticket per vehicle for up to 6 adults. All sp... |
| SunDec 21 | 6:40 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
 | SunDec 21 | 7:00 PM | Sugarman Allstars Ft. Special Guests Fre... | Music | Blues | Reggies Bananna's Shack | 2105 South State Street | All Ages | Free |
 | SunDec 21 | 7:00 PM | Santa's Secret | Fairs & Festivals | Pioneer Court | 401 N Michigan Ave | All Ages | Free | |
| SunDec 21 | 7:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| SunDec 21 | 7:00 PM | Drunk Shakespeare - 21+ | Art & Theatre | Miscellaneous | The Lion Theatre | 182 N Wabash Ave | All Ages | Free |
| SunDec 21 | 7:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| SunDec 21 | 7:40 PM | Light of Christmas Drive Thru | Family | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
 | SunDec 21 | 8:00 PM | Cryoflove, Enoch7thprophet, Elysium Nigh... | Music | Rock | Reggies Music Joint | 2105 South State Street | All Ages | Free |
| SunDec 21 | 8:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
 | SunDec 21 | 8:00 PM | Disco Biscuits (17 and Over) - Sunday | Music | Rock | Thalia Hall | 1807 S Allport Street | All Ages | Free |
SunDec 21 | 8:00 PM | The Disco Biscuits Fall Tour 2025 presen... | Music | Alternative | Thalia Hall | 1807 S Allport St | All Ages | Free | |
| SunDec 21 | 8:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
SunDec 21 | 8:30 PM | ChiTown Drive-In Presents - Elf | Family | ChiTown Movies | 2343 S Throop St | All Ages | Free One ticket per vehicle for up to 6 adults. All sp... | ||
| SunDec 21 | 8:40 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
 | SunDec 21 | 9:00 PM | Sophia Lucia and the Freaks / DJ Skoli | Music | Other | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
 | MonDec 22 | 11:00 AM | Vip Stadium Tour | Sports | Miscellaneous | Soldier Field | 1410 S. Museum Campus Drive | All Ages | Free |
| MonDec 22 | 1:00 PM | Vip Stadium Tour | Sports | Miscellaneous | Soldier Field | 1410 S. Museum Campus Drive | All Ages | Free |
| MonDec 22 | 3:00 PM | Vip Stadium Tour | Sports | Miscellaneous | Soldier Field | 1410 S. Museum Campus Drive | All Ages | Free |
| MonDec 22 | 5:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| MonDec 22 | 5:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| MonDec 22 | 5:40 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
 | MonDec 22 | 6:00 PM | Loyola Ramblers Womens Basketball vs. Au... | Sports | Basketball | Gentile Arena | 1032 W Sheridan Rd | All Ages | Free |
| MonDec 22 | 6:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| MonDec 22 | 6:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| MonDec 22 | 6:40 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| MonDec 22 | 7:00 PM | Light of Christmas Drive Thru | Family | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| MonDec 22 | 7:00 PM | Drunk Shakespeare - 21+ | Art & Theatre | Miscellaneous | The Lion Theatre | 182 N Wabash Ave | All Ages | Free |
| MonDec 22 | 7:20 PM | Light of Christmas Drive Thru | Family | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| MonDec 22 | 7:30 PM | Merry, Merry Chicago! w/ Chicago Symphon... | Music | Orchestra Hall - IL | 220 S. Michigan Ave. | All Ages | Free | |
| MonDec 22 | 7:40 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| MonDec 22 | 8:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| MonDec 22 | 8:00 PM | Santa's Secret | Fairs & Festivals | Pioneer Court | 401 N Michigan Ave | All Ages | Free | |
| MonDec 22 | 8:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| MonDec 22 | 9:00 PM | FREE MONDAY w/ Sidaka / Syd Falls / Nois... | Music | Other | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
| MonDec 22 | 9:00 PM | Drunk Shakespeare - 21+ | Art & Theatre | Miscellaneous | The Lion Theatre | 182 N Wabash Ave | All Ages | Free |
| TueDec 23 | 1:00 PM | Merry, Merry Chicago! w/ Chicago Symphon... | Music | Orchestra Hall - IL | 220 S. Michigan Ave. | All Ages | Free | |
| TueDec 23 | 2:00 PM | Joffrey Ballet presents The Nutcracker | Art & Theatre | Civic Opera House | 20 N. Wacker Dr. | All Ages | Free | |
| TueDec 23 | 4:00 PM | 'Twas the Night Before... by Cirque du S... | Art & Theatre | Circus & Specialty Acts | The Chicago Theatre | 175 N State St | All Ages | Free |
| TueDec 23 | 4:30 PM | Merry, Merry Chicago! w/ Chicago Symphon... | Music | Orchestra Hall - IL | 220 S. Michigan Ave. | All Ages | Free | |
| TueDec 23 | 5:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| TueDec 23 | 5:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| TueDec 23 | 5:40 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| TueDec 23 | 6:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| TueDec 23 | 6:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| TueDec 23 | 6:40 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| TueDec 23 | 7:00 PM | 'Twas the Night Before... by Cirque du S... | Art & Theatre | Circus & Specialty Acts | The Chicago Theatre | 175 N State St | All Ages | Free |
| TueDec 23 | 7:00 PM | Joffrey Ballet presents The Nutcracker | Art & Theatre | Civic Opera House | 20 N. Wacker Dr. | All Ages | Free | |
| TueDec 23 | 7:00 PM | Drunk Shakespeare - 21+ | Art & Theatre | Miscellaneous | The Lion Theatre | 182 N Wabash Ave | All Ages | Free |
| TueDec 23 | 7:00 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| TueDec 23 | 7:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| TueDec 23 | 7:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| TueDec 23 | 7:40 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| TueDec 23 | 8:00 PM | Santa's Secret | Fairs & Festivals | Pioneer Court | 401 N Michigan Ave | All Ages | Free | |
 | TueDec 23 | 8:00 PM | Chicago Blackhawks vs. Philadelphia Flye... | Sports | Hockey | United Center | 1901 W Madison | All Ages | Free |
| TueDec 23 | 8:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| TueDec 23 | 8:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| TueDec 23 | 9:00 PM | Faceoff V: A Night of Tiny Challenges | Fairs & Festivals | Empty Bottle | 1035 N. Western Ave. | All Ages | Free | |
| TueDec 23 | 9:00 PM | Drunk Shakespeare - 21+ | Art & Theatre | Miscellaneous | The Lion Theatre | 182 N Wabash Ave | All Ages | Free |
| WedDec 24 | 12:00 PM | 'Twas the Night Before... by Cirque du S... | Art & Theatre | Circus & Specialty Acts | The Chicago Theatre | 175 N State St | All Ages | Free |
| WedDec 24 | 1:00 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| WedDec 24 | 2:00 PM | Joffrey Ballet presents The Nutcracker | Art & Theatre | Civic Opera House | 20 N. Wacker Dr. | All Ages | Free | |
| WedDec 24 | 3:00 PM | 'Twas the Night Before... by Cirque du S... | Art & Theatre | Circus & Specialty Acts | The Chicago Theatre | 175 N State St | All Ages | Free |
| WedDec 24 | 5:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| WedDec 24 | 5:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| WedDec 24 | 5:40 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| WedDec 24 | 6:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| WedDec 24 | 6:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| WedDec 24 | 6:40 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| WedDec 24 | 7:00 PM | Drunk Shakespeare - 21+ | Art & Theatre | Miscellaneous | The Lion Theatre | 182 N Wabash Ave | All Ages | Free |
| WedDec 24 | 7:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| WedDec 24 | 7:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| WedDec 24 | 7:40 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| WedDec 24 | 8:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| WedDec 24 | 8:00 PM | Santa's Secret | Fairs & Festivals | Pioneer Court | 401 N Michigan Ave | All Ages | Free | |
| WedDec 24 | 8:20 PM | Light of Christmas Drive Thru | Family | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
ThuDec 25 | 5:00 PM | ChiTown Drive-In Presents - Home Alone | Family | ChiTown Movies | 2343 S Throop St | All Ages | Free One ticket per vehicle for up to 6 adults. All sp... | ||
| ThuDec 25 | 5:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| ThuDec 25 | 5:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| ThuDec 25 | 5:40 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| ThuDec 25 | 6:00 PM | Closed for Christmas Holiday | Music | Blues | Kingston Mines - Chicago Blues Center | 2548 North Halsted | All Ages | Free |
| ThuDec 25 | 6:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| ThuDec 25 | 6:00 PM | Christmas with the Chrunks | Fairs & Festivals | Empty Bottle | 1035 N. Western Ave. | All Ages | Free | |
| ThuDec 25 | 6:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| ThuDec 25 | 6:40 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
ThuDec 25 | 7:00 PM | ChiTown Drive-In Presents - Elf | Family | ChiTown Movies | 2343 S Throop St | All Ages | Free One ticket per vehicle for up to 6 adults. All sp... | ||
| ThuDec 25 | 7:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| ThuDec 25 | 7:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| ThuDec 25 | 7:40 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| ThuDec 25 | 8:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| ThuDec 25 | 8:00 PM | Santa's Secret | Family | Pioneer Court | 401 N Michigan Ave | All Ages | Free | |
| ThuDec 25 | 8:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
 | ThuDec 25 | 8:30 PM | ChiTown Drive-In Presents - The Grinch w... | Family | ChiTown Movies | 2343 S Throop St | All Ages | Free All spaces have excellent views of our large scree... | |
 | ThuDec 25 | 9:00 PM | Mr. Blotto @ Cubby Bear LIVE! | Music | Rock | Cubby Bear | 1059 West Addison | All Ages | Free |
| FriDec 26 | 1:00 PM | 'Twas the Night Before... by Cirque du S... | Art & Theatre | Circus & Specialty Acts | The Chicago Theatre | 175 N State St | All Ages | Free |
| FriDec 26 | 1:00 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| FriDec 26 | 2:00 PM | Joffrey Ballet presents The Nutcracker | Art & Theatre | Civic Opera House | 20 N. Wacker Dr. | All Ages | Free | |
| FriDec 26 | 3:00 PM | Drunk Shakespeare - 21+ | Art & Theatre | Miscellaneous | The Lion Theatre | 182 N Wabash Ave | All Ages | Free |
| FriDec 26 | 4:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| FriDec 26 | 4:00 PM | 'Twas the Night Before... by Cirque du S... | Art & Theatre | Circus & Specialty Acts | The Chicago Theatre | 175 N State St | All Ages | Free |
| FriDec 26 | 5:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| FriDec 26 | 5:00 PM | Santa's Secret | Fairs & Festivals | Pioneer Court | 401 N Michigan Ave | All Ages | Free | |
| FriDec 26 | 5:00 PM | Drunk Shakespeare - 21+ | Art & Theatre | Miscellaneous | The Lion Theatre | 182 N Wabash Ave | All Ages | Free |
| FriDec 26 | 5:20 PM | Light of Christmas Drive Thru | Family | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
 | FriDec 26 | 5:30 PM | Hard Country Honky Tonk with The Hoyle B... | Music | Country | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
| FriDec 26 | 5:40 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| FriDec 26 | 6:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| FriDec 26 | 6:00 PM | Next Showcase USA | Music | Other | Foundation Room at House of Blues Chicag... | 329 N Dearborn St | All Ages | Free |
| FriDec 26 | 6:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
FriDec 26 | 6:30 PM | Chicago Bulls vs. Philadelphia 76ers | Sports | Basketball | United Center | 1901 W Madison | All Ages | Free | |
| FriDec 26 | 6:40 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| FriDec 26 | 7:00 PM | Drunk Shakespeare - 21+ | Art & Theatre | Miscellaneous | The Lion Theatre | 182 N Wabash Ave | All Ages | Free |
| FriDec 26 | 7:00 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
 | FriDec 26 | 7:00 PM | Pier Pressure Chicago ft Subtronics - Fr... | Music | Other | Navy Pier | 600 E. Grand Ave. | All Ages | Free |
| FriDec 26 | 7:00 PM | Joffrey Ballet presents The Nutcracker | Art & Theatre | Civic Opera House | 20 N. Wacker Dr. | All Ages | Free | |
| FriDec 26 | 7:00 PM | Diva Royale Drag Queen Show - 21+ | Art & Theatre | Primary Night Club | 5 W Division St | All Ages | Free | |
| FriDec 26 | 7:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| FriDec 26 | 7:00 PM | Vino Louden Blues Band/Nicholas Alexande... | Music | Blues | Kingston Mines - Chicago Blues Center | 2548 North Halsted | All Ages | Free |
| FriDec 26 | 7:20 PM | Light of Christmas Drive Thru | Family | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| FriDec 26 | 7:40 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
 | FriDec 26 | 8:00 PM | Moon Taxi | Music | Rock | Garcia's Chicago | 1001 W Washington Blvd | All Ages | Free |
| FriDec 26 | 8:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| FriDec 26 | 8:00 PM | Santa's Secret | Fairs & Festivals | Pioneer Court | 401 N Michigan Ave | All Ages | Free | |
| FriDec 26 | 8:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
 | FriDec 26 | 8:30 PM | The T.V. Show! | Music | R&B | Reggie's Rock Club | 2105 South State Street | All Ages | Free |
| FriDec 26 | 8:40 PM | Light of Christmas Drive Thru | Family | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
 | FriDec 26 | 9:00 PM | Zombie Maã±Ana, Caught On Cline | Music | Jazz | Reggies Music Joint | 2105 South State Street | All Ages | Free |
| FriDec 26 | 9:00 PM | 80s Xmas with TrakQwn (DJ) | Music | Other | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
| FriDec 26 | 9:00 PM | Drunk Shakespeare - 21+ | Art & Theatre | Miscellaneous | The Lion Theatre | 182 N Wabash Ave | All Ages | Free |
| FriDec 26 | 9:30 PM | Yankee Cowboy | Music | Country | Carol's Pub | 4659 North Clark Street | All Ages | Free |
 | FriDec 26 | 10:00 PM | Transitions x Tengo Funk Present: Andre ... | Music | Pop | Outset | 1675 N Elston Ave | All Ages | Free |
 | FriDec 26 | 10:00 PM | Andre Power (18 and Over) | Music | Dance/Electronic | Concord Music Hall | 2047 N. Milwaukee | All Ages | Free |
| FriDec 26 | 10:30 PM | No Agenda featuring Ndulgnce and Just.On... | Music | Other | Three Top Lounge | 1357 N Elston Avenue | All Ages | Free |
 | SatDec 27 | 11:30 AM | The Rock and Roll Playhouse plays Music ... | Music | Rock | Thalia Hall | 1807 S Allport St | All Ages | Free |
| SatDec 27 | 1:00 PM | 'Twas the Night Before... by Cirque du S... | Art & Theatre | Circus & Specialty Acts | The Chicago Theatre | 175 N State St | All Ages | Free |
| SatDec 27 | 1:30 PM | Diva Royale Drag Queen Show - 21+ | Art & Theatre | Primary Night Club | 5 W Division St | All Ages | Free | |
| SatDec 27 | 2:00 PM | Joffrey Ballet presents The Nutcracker | Art & Theatre | Civic Opera House | 20 N. Wacker Dr. | All Ages | Free | |
| SatDec 27 | 2:00 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| SatDec 27 | 3:00 PM | Drunk Shakespeare - 21+ | Art & Theatre | Miscellaneous | The Lion Theatre | 182 N Wabash Ave | All Ages | Free |
| SatDec 27 | 4:00 PM | 'Twas the Night Before... by Cirque du S... | Art & Theatre | Circus & Specialty Acts | The Chicago Theatre | 175 N State St | All Ages | Free |
| SatDec 27 | 5:00 PM | Santa's Secret | Fairs & Festivals | Pioneer Court | 401 N Michigan Ave | All Ages | Free | |
| SatDec 27 | 5:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| SatDec 27 | 5:00 PM | Drunk Shakespeare - 21+ | Art & Theatre | Miscellaneous | The Lion Theatre | 182 N Wabash Ave | All Ages | Free |
| SatDec 27 | 5:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| SatDec 27 | 5:40 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| SatDec 27 | 6:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| SatDec 27 | 6:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
 | SatDec 27 | 6:30 PM | Stancyzk w/ Cat Tag, The Bowling Shirts | Music | Alternative | Cubby Bear | 1059 West Addison | All Ages | Free |
| SatDec 27 | 6:40 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| SatDec 27 | 7:00 PM | 'Twas the Night Before... by Cirque du S... | Art & Theatre | Circus & Specialty Acts | The Chicago Theatre | 175 N State St | All Ages | Free |
| SatDec 27 | 7:00 PM | Vino Louden Blues Band/TBA | Music | Blues | Kingston Mines - Chicago Blues Center | 2548 North Halsted | All Ages | Free |
 | SatDec 27 | 7:00 PM | Slo 'Mo presents: Old Gold - The Glamoro... | Music | Three Top Lounge | 1357 N Elston Avenue | All Ages | Free | |
| SatDec 27 | 7:00 PM | Drunk Shakespeare - 21+ | Art & Theatre | Miscellaneous | The Lion Theatre | 182 N Wabash Ave | All Ages | Free |
 | SatDec 27 | 7:00 PM | Holiday of Horror 2025 Edition | Music | Hip-Hop/Rap | Reggie's Rock Club | 2105 South State Street | All Ages | Free |
| SatDec 27 | 7:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
SatDec 27 | 7:00 PM | Chicago Bulls vs. Milwaukee Bucks | Sports | Basketball | United Center | 1901 W Madison | All Ages | Free | |
| SatDec 27 | 7:00 PM | Joffrey Ballet presents The Nutcracker | Art & Theatre | Civic Opera House | 20 N. Wacker Dr. | All Ages | Free | |
 | SatDec 27 | 7:00 PM | Pier Pressure Chicago ft Alison Wonderla... | Music | Other | Navy Pier | 600 E. Grand Ave. | All Ages | Free |
| SatDec 27 | 7:00 PM | Diva Royale Drag Queen Show - 21+ | Art & Theatre | Primary Night Club | 5 W Division St | All Ages | Free | |
| SatDec 27 | 7:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| SatDec 27 | 7:30 PM | The Phantom of the Opera (Chicago) | Art & Theatre | Theatre | Cadillac Palace | 151 W Randolph Street | All Ages | Free |
| SatDec 27 | 7:40 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| SatDec 27 | 8:00 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| SatDec 27 | 8:00 PM | Santa's Secret | Fairs & Festivals | Pioneer Court | 401 N Michigan Ave | All Ages | Free | |
| SatDec 27 | 8:00 PM | Moon Taxi | Music | Rock | Garcia's Chicago | 1001 W Washington Blvd | All Ages | Free |
| SatDec 27 | 8:20 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| SatDec 27 | 8:40 PM | Light of Christmas Drive Thru | Fairs & Festivals | Holiday | Guaranteed Rate Field - Parking Lot A | 3326 S Wentworth Ave | All Ages | Free Chicago's Drive Thru Light Show at White Sox Park ... |
| SatDec 27 | 9:00 PM | Drunk Shakespeare - 21+ | Art & Theatre | Miscellaneous | The Lion Theatre | 182 N Wabash Ave | All Ages | Free |
 | SatDec 27 | 9:00 PM | KPOP CLUB NIGHT XMAS PARTY | Music | Pop | House of Blues Chicago | 329 N Dearborn St | All Ages | Free |
| SatDec 27 | 9:00 PM | Smithsmas | Music | Other | Empty Bottle | 1035 N. Western Ave. | All Ages | Free |
 | SatDec 27 | 9:30 PM | The Messengers | Music | Country | Carol's Pub | 4659 North Clark Street | All Ages | Free |
| SunDec 28 | 10:00 AM | World Famous Gospel Brunch at House of B... | Music | Religious | House of Blues Chicago | 329 N Dearborn St | All Ages | Free |
| SunDec 28 | 12:30 PM | World Famous Gospel Brunch at House of B... | Music | Religious | House of Blues Chicago | 329 N Dearborn St | All Ages | Free |