| Chicago Blackhawks vs. Boston BruinsNHL | Fri Jan 12:00 PM | United Center | from $71 | Tickets |
| Vape! The Grease Parody | Fri Jan 12:30 PM · 7:30 PM | Apollo Theater Chicago | from $57 | Tickets |
| A Drunk Christmas CarolMusical / Play | Fri Jan 15:00 PM · 7:00 PM · 9:00 PM | The Lion Theatre | from $237 | Tickets |
| Aaron WeberComedy | Fri Jan 17:00 PM · 9:15 PM | Zanies Rosemont | from $61 | Tickets |
| Shapel LaceyComedy | Fri Jan 17:00 PM | Zanies Chicago (Old Town) | from $75 | Tickets |
| Chicago Steel vs. Muskegon LumberjacksHockey | Sat Jan 212:00 AM | USG Arena | from $20 | Tickets |
| DePaul Blue Demons vs. Providence FriarsCollege basketball | Sat Jan 2TBA | Wintrust Arena | from $26 | Tickets |
| Potted PotterMusical / Play | Sat Jan 21:00 PM · 7:30 PM | Broadway Playhouse | from $91 | Tickets |
| A Midsummer Night's DreamMusical / Play | Sat Jan 22:00 PM · 7:00 PM | Chicago Shakespeare (Courtyard) | from $89 | Tickets |
| Vape! The Grease Parody | Sat Jan 22:30 PM · 7:30 PM | Apollo Theater Chicago | from $57 | Tickets |
| A Drunk Christmas CarolMusical / Play | Sat Jan 23:00 PM · 5:00 PM · 7:00 PM · 9:00 PM | The Lion Theatre | from $184 | Tickets |
| Aaron WeberComedy | Sat Jan 26:30 PM · 8:45 PM | Zanies Rosemont | from $61 | Tickets |
| 3Ball MTYLatin | Sat Jan 27:00 PM | Aon Grand Ballroom Navy Pier | from $94 | Tickets |
| Chicago Bulls vs. Los Angeles LakersNBA | Sat Jan 27:00 PM | United Center | from $163 | Tickets |
| Chicago Wolves vs. Iowa WildAhl | Sat Jan 27:00 PM | Allstate Arena | from $33 | Tickets |
| Ronnie Baker BrooksJazz / Blues | Sat Jan 27:30 PM | City Winery Chicago | from $121 | Tickets |
| Northwestern Wildcats vs. Minnesota Golden GophersCollege basketball | Sun Jan 3TBA | Welsh-Ryan Arena (Northwestern) | from $98 | Tickets |
| Potted PotterMusical / Play | Sun Jan 31:00 PM · 6:30 PM | Broadway Playhouse | from $77 | Tickets |
| A Midsummer Night's DreamMusical / Play | Sun Jan 32:00 PM | Chicago Shakespeare (Courtyard) | from $89 | Tickets |
| Vape! The Grease Parody | Sun Jan 32:30 PM | Apollo Theater Chicago | from $58 | Tickets |
| Chicago Bears vs. Detroit LionsNfl | Sun Jan 33:25 PM | Soldier Field | from $199 | Tickets |
| A Drunk Christmas CarolMusical / Play | Sun Jan 35:00 PM · 7:00 PM | The Lion Theatre | from $158 | Tickets |
| Shapel Lacey - ComedianComedy | Sun Jan 36:00 PM | Zanies Rosemont | from $61 | Tickets |
| Chicago Bulls vs. Milwaukee BucksNBA | Tue Jan 57:00 PM | United Center | from $41 | Tickets |
| James StanleyComedy | Tue Jan 57:00 PM | Zanies Chicago (Old Town) | from $74 | Tickets |
| Simone GreenR&B / Soul | Tue Jan 57:30 PM | City Winery Chicago | from $205 | Tickets |
| Chicago Wolves vs. Rockford IceHogsAhl | Wed Jan 67:00 PM | Allstate Arena | from $22 | Tickets |
| Simone GreenR&B / Soul | Wed Jan 67:30 PM | City Winery Chicago | from $205 | Tickets |
| Elle VarnerR&B / Soul | Thu Jan 77:30 PM | City Winery Chicago | from $84 | Tickets |
| Matt Rife RescheduledComedy | Thu Jan 78:00 PM | United Center | from $52 | Tickets |
| Led Zeppelin 2 - Tribute Band | Fri Jan 86:30 PM | House of Blues Chicago | from $35 | Tickets |
| Ranaan HershbergComedy | Fri Jan 87:00 PM · 9:15 PM | Zanies Chicago (Old Town) | from $90 | Tickets |
| G. Love & Special SauceAlternative | Fri Jan 88:00 PM | Garcia's Chicago | from $68 | Tickets |
| DePaul Blue Demons vs. Butler BulldogsCollege basketball | Sat Jan 9TBA | Wintrust Arena | from $21 | Tickets |
| Led Zeppelin 2 - Tribute Band | Sat Jan 96:30 PM | House of Blues Chicago | from $35 | Tickets |
| Chicago Wolves vs. Rockford IceHogsAhl | Sat Jan 97:00 PM | Allstate Arena | from $31 | Tickets |
| Ranaan HershbergComedy | Sat Jan 97:00 PM · 9:15 PM | Zanies Chicago (Old Town) | from $93 | Tickets |
| Chicago Wolves vs. Iowa WildAhl | Sun Jan 103:00 PM | Allstate Arena | from $28 | Tickets |
| Rudolf BuchbinderClassical | Sun Jan 103:00 PM | Symphony Center (Orchestra Hall) | from $48 | Tickets |
| Piotr RubikPop / Rock | Sun Jan 106:00 PM | Copernicus Center | from $108 | Tickets |
| NinajirachiPop / Rock | Sun Jan 106:30 PM | Radius - IL | from $78 | Tickets |
| NinajirachiPop / Rock | Mon Jan 116:30 PM | Radius - IL | from $72 | Tickets |
| Chicago Blackhawks vs. Utah MammothNHL | Tue Jan 127:00 PM | United Center | from $29 | Tickets |
| Northwestern Wildcats vs. Illinois Fighting IlliniCollege basketball | Wed Jan 13TBA | Welsh-Ryan Arena (Northwestern) | from $331 | Tickets |
| MissioAlternative | Wed Jan 138:00 PM | Beat Kitchen | from $45 | Tickets |
| Chicago Bulls vs. Minnesota TimberwolvesNBA | Thu Jan 147:00 PM | United Center | from $59 | Tickets |
| Amadeus LiveClassical | Fri Jan 157:00 PM | Lyric Opera House | from $54 | Tickets |
| Shayne SmithComedy | Fri Jan 157:00 PM · 9:15 PM | Zanies Rosemont | from $90 | Tickets |
| Anna Von HausswolffClassical | Fri Jan 158:00 PM | Thalia Hall | from $36 | Tickets |
| Braxton KeithCountry / Folk | Fri Jan 158:00 PM | Joe's Live | from $47 | Tickets |
| Northwestern Wildcats vs. Rutgers Scarlet KnightsCollege basketball | Sat Jan 16TBA | Welsh-Ryan Arena (Northwestern) | from $76 | Tickets |
| Amadeus LiveClassical | Sat Jan 162:00 PM | Lyric Opera House | from $54 | Tickets |
| Seth MeyersComedy | Sat Jan 165:00 PM · 8:00 PM | The Chicago Theatre | from $79 | Tickets |
| Chicago Blackhawks vs. Detroit Red WingsNHL | Sat Jan 166:00 PM | United Center | from $88 | Tickets |
| The Jazz Room - A Journey to the Heart of New Orleans | Sat Jan 166:00 PM · 8:00 PM | The Den Theatre (Heath Mainstage) | from $292 | Tickets |
| Shayne SmithComedy | Sat Jan 166:30 PM · 8:45 PM | Zanies Rosemont | from $92 | Tickets |
| Chicago Wolves vs. San Jose BarracudaAhl | Sat Jan 167:00 PM | Allstate Arena | from $33 | Tickets |
| Dominique HammonsJazz / Blues | Sat Jan 167:30 PM | Studebaker Theater | from $155 | Tickets |
| Chicago Bulls vs. Toronto RaptorsNBA | Sun Jan 172:30 PM | United Center | from $40 | Tickets |
| Chicago Wolves vs. San Jose BarracudaAhl | Sun Jan 173:00 PM | Allstate Arena | from $28 | Tickets |
| Usama SiddiqueeComedy | Mon Jan 187:00 PM | Vic Theatre | from $57 | Tickets |
| Chicago Blackhawks vs. Calgary FlamesNHL | Mon Jan 187:30 PM | United Center | from $40 | Tickets |
| DePaul Blue Demons vs. St. Johns Red StormCollege basketball | Tue Jan 19TBA | Wintrust Arena | from $23 | Tickets |
| Chicago Blackhawks vs. Dallas StarsNHL | Wed Jan 206:30 PM | United Center | from $35 | Tickets |
| Fumi AbeComedy | Thu Jan 217:00 PM | Zanies Chicago (Old Town) | from $90 | Tickets |
| DePaul Blue Demons vs. Villanova WildcatsCollege basketball | Fri Jan 22TBA | Wintrust Arena | from $23 | Tickets |
| Chicago Blackhawks vs. Vancouver CanucksNHL | Fri Jan 227:00 PM | United Center | from $49 | Tickets |
| Fumi AbeComedy | Fri Jan 227:00 PM · 9:15 PM | Zanies Chicago (Old Town) | from $90 | Tickets |
| Haydn's The CreationClassical | Fri Jan 227:00 PM | Lyric Opera House | from $81 | Tickets |
| Tennessee Whiskey - Tribute to Chris Stapleton | Fri Jan 228:00 PM | Joes on Weed Street | from $35 | Tickets |
| TwinsickTechno / Electronic | Fri Jan 228:00 PM | The Salt Shed (Indoors) | from $65 | Tickets |
| Chicago Steel vs. Dubuque Fighting SaintsHockey | Sat Jan 2312:00 AM | USG Arena | from $20 | Tickets |
| Chicago Bulls vs. Philadelphia 76ersNBA | Sat Jan 234:00 PM | United Center | from $156 | Tickets |
| Denny LoveComedy | Sat Jan 237:00 PM | Vic Theatre | from $45 | Tickets |
| Fumi AbeComedy | Sat Jan 237:00 PM · 9:15 PM | Zanies Chicago (Old Town) | from $91 | Tickets |
| Haydn's The CreationClassical | Sat Jan 237:30 PM | Lyric Opera House | from $99 | Tickets |
| Know GoodTechno / Electronic | Sat Jan 239:00 PM | Ramova Theatre | from $51 | Tickets |
| The Jury Experience: An Immersive Courtroom Case | Sun Jan 244:30 PM · 7:00 PM | Museum of Contemporary Art Chicago | from $113 | Tickets |
| Chicago Blackhawks vs. Vegas Golden KnightsNHL | Sun Jan 246:00 PM | United Center | from $55 | Tickets |
| Chicago Bulls vs. Dallas MavericksNBA | Mon Jan 257:00 PM | United Center | from $45 | Tickets |
| Northwestern Wildcats vs. Indiana HoosiersCollege basketball | Wed Jan 27TBA | Welsh-Ryan Arena (Northwestern) | from $244 | Tickets |
| Alex FalconeComedy | Thu Jan 287:00 PM | Zanies Chicago (Old Town) | from $58 | Tickets |
| Yonder Mountain String BandAlternative | Thu Jan 288:00 PM | SPACE (Evanston) | from $85 | Tickets |
| Chicago Steel vs. Fargo ForceHockey | Fri Jan 2912:00 AM | USG Arena | from $19 | Tickets |
| LevityTechno / Electronic | Fri Jan 29TBA | Festival Hall A at Navy Pier | from $112 | Tickets |
| Levity - 2 Day PassTechno / Electronic | Fri Jan 29TBA | Festival Hall A at Navy Pier | from $199 | Tickets |
| Alex FalconeComedy | Fri Jan 297:00 PM · 9:15 PM | Zanies Chicago (Old Town) | from $58 | Tickets |
| Romeo y Julieta (Romeo and Juliet)Musical / Play | Fri Jan 297:00 PM | Chicago Shakespeare (Courtyard) | from $89 | Tickets |
| Chicago Symphony Orchestra: West Side Story - Film with OrchestraClassical | Fri Jan 297:30 PM | Symphony Center (Orchestra Hall) | from $75 | Tickets |
| Chicago Steel vs. Fargo ForceHockey | Sat Jan 3012:00 AM | USG Arena | from $20 | Tickets |
| DePaul Blue Demons vs. Xavier MusketeersCollege basketball | Sat Jan 30TBA | Wintrust Arena | from $26 | Tickets |
| LevityTechno / Electronic | Sat Jan 30TBA | Festival Hall A at Navy Pier | from $116 | Tickets |
| Northwestern Wildcats vs. USC TrojansCollege basketball | Sat Jan 30TBA | Welsh-Ryan Arena (Northwestern) | from $120 | Tickets |
| Alex FalconeComedy | Sat Jan 307:00 PM · 9:15 PM | Zanies Chicago (Old Town) | from $58 | Tickets |
| Chicago Wolves vs. Grand Rapids GriffinsAhl | Sat Jan 307:00 PM | Allstate Arena | from $28 | Tickets |
| Romeo y Julieta (Romeo and Juliet)Musical / Play | Sat Jan 307:00 PM | Chicago Shakespeare (Courtyard) | from $89 | Tickets |
| Chicago Symphony Orchestra: West Side Story - Film with OrchestraClassical | Sat Jan 307:30 PM | Symphony Center (Orchestra Hall) | from $75 | Tickets |
| Wicked - Part One In ConcertClassical | Sat Jan 307:30 PM | Auditorium Theatre | from $85 | Tickets |
| Sin BanderaLatin | Sat Jan 308:00 PM | Rosemont Theatre | from $78 | Tickets |
| Chicago Wolves vs. Hartford Wolf PackAhl | Sun Jan 313:00 PM | Allstate Arena | from $28 | Tickets |
| Mitsuko UchidaClassical | Sun Jan 313:00 PM | Symphony Center (Orchestra Hall) | from $48 | Tickets |
| Jane EugeneR&B / Soul | Sun Jan 315:00 PM · 8:30 PM | City Winery Chicago | from $90 | Tickets |
