Below is a list of 366 events active for Chicago, organized alphabetically. If you don't see your event listed, please add your event.
| .38 Special | St. Charles | Music - Rock & Metal |
| 2019 Country LakeShake - Sunday | Chicago | Festivals - Music |
| 2019 Riot Fest Chicago - Friday | Chicago | Festivals - Music |
| A Chorus Line | Chicago | Performance - Musical |
| Adam Calhoun | Hillside | Music - Country & Folk |
| Advocate Health Care International Chicago 5K | Chicago | Health & Fitness |
| AJ Mitchell | Chicago | Music - Rock & Metal |
| Amanda Palmer | Chicago | Music - Alternative Rock |
| American Ballet Theatre: Whipped Cream | Chicago | Performance - Ballet |
| American English - Beatles Tribute | Berwyn | Miscellaneous |
| Anastasia | Chicago | Performance - Musical |
| Andrea Gibson | Chicago | Educational - Class |
| Ariana Grande | Chicago | Arts - Concerts |
| August Rush | Aurora | Performance - Musical |
| Automate 2019 | Chicago | Business - Conference |
| B - The Underwater Bubble Show | Waukegan | Performance - Theater |
| Backstreet Boys | Chicago | Music - Rock & Metal |
| Bad Suns | Chicago | Music - Alternative Rock |
| Banda MS | Rosemont | Music - Latin |
| Bandoleros | Evanston | Music - Latin |
| Bank of America Chicago Marathon | Chicago | Health & Fitness |
| Bayonne | Chicago | Music - Alternative Rock |
| BB King's Blues Band | St. Charles | Music - Soul / R & B |
| BBMak | Chicago | Music - Rock & Metal |
| Bible Bingo | Chicago | Performance |
| Bill Maher | Chicago | Performance - Comedic |
| Billy Idol | Naperville | Music - Rock & Metal |
| Blaze Bayley | Hillside | Music - Rock & Metal |
| Blue Man Group | Chicago | Performance - Theater |
| Blue Man Group | Chicago | |
| Brian McKnight | Hammond | Music - Soul / R & B |
| Bring It! Live | Chicago | Performance - Dance |
| Broken Arrow | St. Charles | Miscellaneous |
| Bryan Ferry | Chicago | Music - Rock & Metal |
| Bunny Rock 5K & Egg Hunt | Vernon Hills | Health - Fundraiser Walk / Run / Bike |
| Bunny Rock Chicago | Chicago | Health - Fundraiser Walk / Run / Bike |
| Bye Bye Liver: The Chicago Drinking Play | Chicago | Performance - Theater |
| Carrie Underwood | Chicago | Arts - Concerts |
| Casey - Band | Chicago | Music - Alternative Rock |
| Cast Of Impractical Jokers | Tinley Park | Performance - Comedic |
| Cat & Nat Live | Chicago | Miscellaneous |
| Cats | Chicago | Performance - Musical |
| Celtic Woman | Rosemont | Arts - Concerts |
| Chayanne | Rosemont | Music - Latin |
| Cheer Fitness: A Cheerleading/Dance Fusion Aerobics Class | Chicago | Health & Fitness |
| Chicago - The Musical | Chicago | Performance - Musical |
| Chicago Bar Association Symphony Orchestra & Chorus: Beethoven, Mozart… | Chicago | Arts - Concerts |
| Chicago Blackhawks vs Dallas Stars | Chicago | Sports - Hockey |
| Chicago Blackhawks vs St. Louis Blues | Chicago | Sports - Hockey |
| Chicago Bliss vs. Atlanta Steam | Hoffman Estates | Sports |
| Chicago Bliss vs. Nashville Knights | Hoffman Estates | Sports |
| Chicago Bulls vs New York Knicks | Chicago | Sports - Pro Basketball |
| Chicago Bulls vs. Philadelphia 76ers | Chicago | Sports - Pro Basketball |
| Chicago Cubs vs. Chicago White Sox | Chicago | Sports - Pro Baseball |
| Chicago Cubs vs. Cincinnati Reds | Chicago | Sports - Pro Baseball |
| Chicago Cubs vs. Pittsburgh Pirates | Chicago | Sports - Pro Baseball |
| Chicago Cubs vs. San Francisco Giants | Chicago | Sports - Pro Baseball |
| Chicago Cubs vs. Arizona Diamondbacks | Chicago | Sports - Pro Baseball |
| Chicago Cubs vs. Atlanta Braves | Chicago | Sports - Pro Baseball |
| Chicago Cubs vs. Colorado Rockies | Chicago | Sports - Pro Baseball |
| Chicago Cubs vs. Los Angeles Angels of Anaheim | Chicago | Sports - Pro Baseball |
| Chicago Cubs vs. Los Angeles Dodgers | Chicago | Sports - Pro Baseball |
| Chicago Cubs vs. Miami Marlins | Chicago | Sports - Pro Baseball |
| Chicago Cubs vs. Milwaukee Brewers | Chicago | Sports - Pro Baseball |
| Chicago Cubs vs. New York Mets | Chicago | Sports - Pro Baseball |
| Chicago Cubs vs. Oakland Athletics | Chicago | Sports |
| Chicago Cubs vs. Phildelphia Phillies | Chicago | Sports - Pro Baseball |
| Chicago Cubs vs. San Diego Padres | Chicago | Sports - Pro Baseball |
| Chicago Cubs vs. Seattle Mariners | Chicago | Sports - Pro Baseball |
| Chicago Cubs vs. St. Louis Cardinals | Chicago | Sports - Pro Baseball |
| Chicago Fire vs. Atlanta United FC | Bridgeview | Sports - Soccer |
| Chicago Fire vs. FC Dallas | Bridgeview | Sports - Soccer |
| Chicago Fire vs. Minnesota United FC | Bridgeview | Sports - Soccer |
| Chicago Fire vs. Montreal Impact | Bridgeview | Sports - Soccer |
| Chicago Fire vs. Vancouver Whitecaps FC | Bridgeview | Sports - Soccer |
| Chicago Gourmet - Sunday | Chicago | Festivals |
| Chicago Open Air Festival: Tool & The Prodigy - Sunday Pass | Bridgeview | Festivals - Music |
| Chicago Philharmonic & Cirque de la Symphonie | Chicago | Performance |
| Chicago Sky vs. Dallas Wings | Chicago | Sports |
| Chicago Sky vs. Indiana Fever | Chicago | Sports |
| Chicago Sky vs. Los Angeles Sparks | Chicago | Sports |
| Chicago Sky vs. New York Liberty | Chicago | Sports |
| Chicago Sky vs. Phoenix Mercury | Chicago | Sports |
| Chicago Sky vs. Washington Mystics | Chicago | Sports |
| Chicago Symphony Orchestra Family Matinee: Thomas Wilkins - Pictures... | Chicago | Arts - Concerts |
| Chicago Symphony Orchestra: Emmanuel Krivine - Chopin & The Mermaid… | Chicago | Arts - Concerts |
| Chicago Symphony Orchestra: Fabien Gabel & Emanuel Ax - Brahms Piano Concerto... | Chicago | Arts - Concerts |
| Chicago Symphony Orchestra: Fabien Gabel & Emanuel Ax - Brahms' Piano Concerto... | Chicago | Arts - Concerts |
| Chicago Symphony Orchestra: Giancarlo Guerrero - Rodrigo Concierto de… | Chicago | Arts - Concerts |
| Chicago Symphony Orchestra: Jakub Hrusa - Shostakovich 9 | Chicago | Arts - Concerts |
| Chicago Symphony Orchestra: Jakub Hrusa - Shostakovich Symphony No. 9... | Chicago | Arts - Concerts |
| Chicago Symphony Orchestra: Matthias Pintscher & The Joffrey Ballet -… | Chicago | Arts - Concerts |
| Chicago Symphony Orchestra: Mikko Franck - Sibelius Violin Concerto… | Chicago | Arts - Concerts |
| Chicago Symphony Orchestra: Nikolaj Znaider - Mahler 1 | Chicago | Arts - Concerts |
| Chicago Symphony Orchestra: Riccardo Muti - An American In Paris... | Chicago | Arts - Concerts |
| Chicago Symphony Orchestra: Riccardo Muti - Pines of Rome | Chicago | Arts - Concerts |
| Chicago Symphony Orchestra: Riccardo Muti - Uchida & Mozart | Chicago | Arts - Concerts |
| Chicago Symphony Orchestra: Riccardo Muti - Verdi Aida | Chicago | Arts - Concerts |
| Chicago Symphony Orchestra: Simone Young - Wagner & Brahms | Chicago | Arts - Concerts |
| Chicago White Sox vs. Baltimore Orioles | Chicago | Sports - Pro Baseball |
| Chicago White Sox vs. Boston Red Sox | Chicago | Sports - Pro Baseball |
| Chicago White Sox vs. Cleveland Indians | Chicago | Sports - Pro Baseball |
| Chicago White Sox vs. Detroit Tigers | Chicago | Sports - Pro Baseball |
| Chicago White Sox vs. Houston Astros | Chicago | Sports - Pro Baseball |
| Chicago White Sox vs. Kansas City Royals | Chicago | Sports - Pro Baseball |
| Chicago White Sox vs. Los Angeles Angels of Anaheim | Chicago | Sports - Pro Baseball |
| Chicago White Sox vs. Miami Marlins | Chicago | Sports - Pro Baseball |
| Chicago White Sox vs. Minnesota Twins | Chicago | Sports - Pro Baseball |
| Chicago White Sox vs. New York Mets | Chicago | Sports - Pro Baseball |
| Chicago White Sox vs. New York Yankees | Chicago | Sports - Pro Baseball |
| Chicago White Sox vs. Oakland Athletics | Chicago | Sports - Pro Baseball |
| Chicago White Sox vs. Seattle Mariners | Chicago | Sports - Pro Baseball |
| Chicago White Sox vs. Texas Rangers | Chicago | Sports - Pro Baseball |
| Chicago White Sox vs. Toronto Blue Jays | Chicago | Sports - Pro Baseball |
| Chicago White Sox vs. Washington Nationals | Chicago | Sports - Pro Baseball |
| Chicago Wingfest | Chicago | Festivals - Music |
| Chicago Wolves vs. Colorado Eagles | Rosemont | Sports |
| Children's Story Hour | Chicago | Kids - Children's Activities |
| Chris D'Elia | Chicago | Performance - Comedic |
| Cirque du Soleil - Volta | Chicago | Performance - Circus / Animal Show |
| Citizen Cope | Chicago | Arts - Concerts |
| Classic Encounter Lecture | Chicago | Educational - Class |
| Cocktails and Clay | Chicago | Community |
| Come From Away | Chicago | Performance - Musical |
| Comedysportz4kidz | Chicago | Performance - Comedic |
| Common & Chicago Symphony Orchestra | Chicago | Music - Hip Hop & Rap |
| Conan Gray | Chicago | Music - Rock & Metal |
| Corduroy | Chicago | Performance - Musical |
| Cornerstones of Rock | St. Charles | Music - Rock & Metal |
| Country in the City Presents: David St. Romain with Cross County Junction... | Chicago | Nightlife - Live Music |
| Country Inn Schaumburg Manager's Reception | Schaumburg | Miscellaneous |
| Cruel Intentions | Chicago | Performance - Musical |
| Crystal Lake Storytime | Crystal Lake | Kids - Children's Activities |
| Cyrille Aimee | Chicago | Music - Jazz |
| Damien Escobar | Chicago | Arts - Concerts |
| Dance Gavin Dance | Chicago | Music - Alternative Rock |
| Darling Grenadine | Lincolnshire | Performance - Musical |
| Dave Davies | Evanston | Music - Rock & Metal |
| Dave Matthews Band | Tinley Park | Music - Alternative Rock |
| David Gray | Chicago | Music - Alternative Rock |
| Dead & Company | Chicago | Arts - Concerts |
| Defying Destiny | Evanston | Arts - Concert - Classical / Symphony |
| Dein Perry's Tap Dogs | Chicago | Performance - Dance |
| Dido | Chicago | Music - Rock & Metal |
| Disney's Beauty and The Beast | St. Charles | Performance - Musical |
| Distant Worlds: The Music from Final Fantasy | Chicago | Arts - Concerts |
| DJEMBE! The Show | Chicago | Performance - Musical |
| Drama Queen & Kevin Lee and The Kings | Hillside | Music - Rock & Metal |
| Eddie Izzard | Chicago | Performance - Comedic |
| Eels | Chicago | Music - Alternative Rock |
| Eifman Ballet Of St. Petersburg: Pygmalion | Chicago | Performance - Ballet |
| El Fantasma | Chicago | Music - Latin |
| Elka | Chicago | Music - New Age & Spiritual |
| EmpoweRun 5K | Chicago | Health - Fundraiser Walk / Run / Bike |
| EnParejaDos: Adrian Uribe & Consuelo Duval | Rosemont | Performance - Comedic |
| Eros Ramazzotti | Rosemont | Music - Latin |
| Evgeny Kissin | Chicago | Arts - Concert - Classical / Symphony |
| Ex Hex & Moaning | Chicago | Music - Alternative Rock |
| Faces Of The King | St. Charles | Miscellaneous |
| Falsettos - The Musical | Chicago | Performance - Musical |
| Flicks and Picks | Crystal Lake | Community - Club |
| Florida Georgia Line, Dan and Shay & Morgan Wallen | Tinley Park | Music - Country & Folk |
| Foals | Chicago | Music - Rock & Metal |
| Footloose - The Musical | Lincolnshire | Performance - Musical |
| Getter | Chicago | Music - Electronic & Trance |
| Gino's East 5k Run/Walk | Chicago | Health - Fundraiser Walk / Run / Bike |
| Ginza Holiday | Chicago | Festivals - Cultural |
| God Is An Astronaut | Chicago | Music - Alternative Rock |
| Guster & Saintseneca | Chicago | Music - Alternative Rock |
| Hamilton | Chicago | Performance - Musical |
| Hamlet | Chicago | Performance - Musical |
| Hands-on Habitat | Chicago | Educational - Science & Nature |
| Harry Potter and the Prisoner of Azkaban In Concert | Chicago | Arts - Concerts |
| Hatebreed | Chicago | Music - Rock & Metal |
| Health | Chicago | Music - Rock & Metal |
| Heartache Tonight - A Tribute to The Eagles | Evanston | Miscellaneous |
| Herman's Hermits & Peter Noone | St. Charles | Music - Rock & Metal |
| Hugh Jackman | Chicago | Performance - Theater |
| Hypocrisy & Fleshgod Apocalypse | Chicago | Music - Rock & Metal |
| Iliza Shlesinger | Chicago | Performance - Comedic |
| Imogen Heap | Chicago | Music - Rock & Metal |
| Intocable | Rosemont | Music - Latin |
| Iration | Chicago | Miscellaneous |
| Iron Maiden | Tinley Park | Music - Rock & Metal |
| Istock Family Look-in Animal Lab | Chicago | Educational - Science & Nature |
| It's Finally Friday | Chicago | Nightlife - Singles |
| Italian Beef 5K | Chicago | Health & Fitness |
| Itzhak Perlman & Evgeny Kissin | Chicago | Arts - Concerts |
| Jawbox | Chicago | Music - Alternative Rock |
| Jay and The Americans | St. Charles | Music - Rock & Metal |
| Jeff Lynne's Electric Light Orchestra | Chicago | Music - Rock & Metal |
| Jeffrey Osborne | Hammond | Music - Soul / R & B |
| Jeremy Loops | Chicago | Music - Country & Folk |
| Jersey Boys | Chicago | Performance - Musical |
| Jimmie Vaughan | St. Charles | Music - Jazz |
| Joel Osteen | Rosemont | Community - Religious |
| Joffrey Ballet: Across the Pond | Chicago | Performance - Ballet |
| John Mayer | Chicago | Music - Rock & Metal |
| Johnny Mathis Christmas Show | Rosemont | Arts - Concerts |
| Johnny Rogers | Evanston | Music - Jazz |
| Jon Anderson | St. Charles | Music - Rock & Metal |
| Jon Bellion | Chicago | Music - Electronic & Trance |
| Jonathan Van Ness | Chicago | Performance - Comedic |
| Judas Priest & Uriah Heep | Rosemont | Music - Rock & Metal |
| Judy Istock Butterfly Haven | Chicago | Educational - Science & Nature |
| Julia Michaels | Chicago | Music - Rock & Metal |
| Junie B. Jones - The Musical | Lincolnshire | Kids Theater |
| Kane County Cougars vs. Beloit Snappers | Geneva | Sports |
| Kane County Cougars vs. Bowling Green Hot Rods | Geneva | Sports |
| Kane County Cougars vs. Burlington Bees | Geneva | Sports |
| Kane County Cougars vs. Cedar Rapids Kernels | Geneva | Sports |
| Kane County Cougars vs. Clinton LumberKings | Geneva | Sports |
| Kane County Cougars vs. Dayton Dragons | Geneva | Sports |
| Kane County Cougars vs. Great Lakes Loons | Geneva | Sports |
| Kane County Cougars vs. Lansing Lugnuts | Geneva | Sports |
| Kane County Cougars vs. Peoria Chiefs | Geneva | Sports |
| Kane County Cougars vs. Quad Cities River Bandits | Geneva | Sports |
| Kane County Cougars vs. Wisconsin Timber Rattlers | Geneva | Sports |
| Kevin Morby | Chicago | Music - Rock & Metal |
| Kid's Storytime at Deerfield's Borders | Deerfield | Kids - Children's Activities |
| La Santa Cecilia | Chicago | Music - Latin |
| Late Night Catechism | Chicago | Performance - Show Comedy |
| Lea Salonga | Chicago | Miscellaneous |
| Lee Fields | Chicago | Music - Soul / R & B |
| Leon | Chicago | Music - Alternative Rock |
| Les Miserables | Chicago | Performance - Musical |
| Lil Mosey | Chicago | Music - Hip Hop & Rap |
| Little River Band | St. Charles | Music - Rock & Metal |
| Lizzo | Chicago | Music - Rock & Metal |
| Lollapalooza - Friday | Chicago | Festivals - Music |
| Lollapalooza - Thursday | Chicago | Festivals - Music |
| Los Angeles Azules | Rosemont | Music - Latin |
| Lovelytheband | Chicago | Music - Rock & Metal |
| Lyric Opera of Chicago: West Side Story | Chicago | Arts - Opera |
| Mac Demarco | Chicago | Music - Rock & Metal |
| Madagascar - A Musical Adventure | Lincolnshire | Kids Theater |
| Mamma Mia! | Oakbrook Terrace | Performance - Musical |
| Mamma Mia! | Oakbrook Terrace | Performance - Musical |
| Manager's Reception at Country Inn | Roselle | Miscellaneous |
| Manila Killa | Chicago | Music - Electronic & Trance |
| Marianas Trench | Chicago | Music - Rock & Metal |
| Marisela | Chicago | Music - Soul / R & B |
| Mark Knopfler | Chicago | Music - Rock & Metal |
| Matilda - The Musical | Oakbrook Terrace | Performance - Musical |
| MC Magic & Lil Rob | Chicago | Music - Hip Hop & Rap |
| Meditation and Christian Mysticism | Chicago | Educational - Class |
| Metaphysical Discussion Group | Crystal Lake | Community - Club |
| Minnie's Boys | Chicago | Performance - Musical |
| Misfits | Rosemont | Music - Alternative Rock |
| Missio | Chicago | Music - Alternative Rock |
| Morris Day and The Time | St. Charles | Music - Soul / R & B |
| Morris Day and The Time & Sheila E | Hammond | Music - Soul / R & B |
| Mott The Hoople '74 | Chicago | Music - Rock & Metal |
| Mr. Eazi | Chicago | Music - New Age & Spiritual |
| Murray Perahia | Chicago | Arts - Concert - Classical / Symphony |
| Murs | Chicago | Music - Hip Hop & Rap |
| Muse & Walk The Moon | Chicago | Music - Rock & Metal |
| Mysteries of the Marsh | Chicago | Educational - Science & Nature |
| Nargiz | Chicago | Music - New Age & Spiritual |
| Nate Bargatze | Chicago | Performance - Comedic |
| National Geographic Live: Point of No Return | Chicago | Educational - Class |
| Neko Case | Chicago | Music - Rock & Metal |
| New Kids On The Block, Salt N Pepa & Naughty by Nature | Rosemont | Music - Rock & Metal |
| Newsboys & Michael W. Smith | Hoffman Estates | Music - New Age & Spiritual |
| Nick Mason's Saucerful of Secrets | Chicago | Music - Rock & Metal |
| Nicky Jam | Rosemont | Music - Hip Hop & Rap |
| Nikki Glaser | Chicago | Performance - Comedic |
| NPC Illinois State Bodybuilding Championship | Chicago | Sports |
| Oliver | Lincolnshire | Performance - Musical |
| Once Upon A Symphony: The Boy and The Violin, A Brazilian Folktale... | Chicago | Performance |
| Open Play Days | Chicago | Kids - Children's Activities |
| Overkill | Chicago | Music - Rock & Metal |
| Pancho Barraza | Rosemont | Music - Latin |
| Papa Roach | Chicago | Music - Alternative Rock |
| Patton Oswalt | Waukegan | Performance - Comedic |
| Paul Reiser | Skokie | Performance - Comedic |
| Perfume | Chicago | Music - Rock & Metal |
| Perpetual Groove | Chicago | Music - Rock & Metal |
| Picture Book Storytime for Infants & Toddlers | Chicago | Kids - Children's Activities |
| Pinot and Piano | Chicago | Arts - Concert - Classical / Symphony |
| Plini | Chicago | Music - Rock & Metal |
| Rain - A Tribute to The Beatles | Chicago | Performance - Musical |
| Rent | Chicago | Performance - Musical |
| REO Speedwagon | Rosemont | Music - Rock & Metal |
| RFID Journal LIVE! Retail @ RetailX | Chicago | Business - Conference |
| Ribfest Chicago | Chicago | Festivals - Culinary |
| Ric Wilson | Chicago | Music - Hip Hop & Rap |
| Rise Against | Chicago | Music - Alternative Rock |
| Rival Sons | Chicago | Music - Rock & Metal |
| River Works | Chicago | Educational - Science & Nature |
| Rock of Ages | Chicago | Performance - Musical |
| Ryan Bingham | Chicago | Music - Country & Folk |
| Sam Savage | St. Charles | Music - Soul / R & B |
| San Holo | Chicago | Music - Electronic & Trance |
| Santana & The Doobie Brothers | Tinley Park | Music - Rock & Metal |
| Shawn Mendes | Rosemont | Arts - Concerts |
| Shy Girls | Chicago | Music - Rock & Metal |
| Silent Sitting | Chicago | Community - Self Help |
| Smucker's Stars on Ice | Rosemont | Sports - Ice Skating |
| Snarky Puppy | Chicago | Music - Jazz |
| Something Rotten | Lincolnshire | Performance - Musical |
| Son Volt | Chicago | Music - Alternative Rock |
| Sound Opinion Series | Evanston | Educational - Class |
| Southside Johnny & The Ashbury Jukes | Evanston | Music - Rock & Metal |
| Southside Johnny and The Asbury Jukes | St. Charles | Music - Rock & Metal |
| Spanish Storytime | Chicago | |
| Steve Martin & Martin Short | Waukegan | Performance - Comedic |
| Steve Martin & Martin Short | Hammond | Performance - Comedic |
| Steven Adler | St. Charles | Music - Rock & Metal |
| Storytime | Chicago | Kids - Children's Activities |
| Storytime at Azizi for Kids! | Matteson | Kids - Children's Activities |
| Storytime Thursday | Chicago | Kids - Children's Activities |
| Straight No Chaser | Joliet | Music - Rock & Metal |
| Studio Drop In | Naperville | Kids - Children's Activities |
| Sweat | Chicago | Performance - Musical |
| SWMRS | Chicago | Music - Rock & Metal |
| Tash Sultana | Highland Park | Music - Rock & Metal |
| TECHSPO Chicago | Chicago | Business - Convention / Expo |
| The 1975 | Chicago | Music - Alternative Rock |
| The Avett Brothers | Chicago | Arts - Concerts |
| The Band's Visit | Chicago | Performance - Musical |
| The Black Cadillacs & Nature Show | Chicago | Nightlife - Live Music |
| The Black Lips | Chicago | Music - Alternative Rock |
| The Claypool Lennon Delirium | Chicago | Music - Alternative Rock |
| The Extreme Green House | Chicago | Educational - Science & Nature |
| The Flat Cats | St. Charles | Music - Jazz |
| The Franchise Show | Rosemont | Business - Convention / Expo |
| The Hives & Refused | Chicago | Music - Alternative Rock |
| The Millennium Tour: B2K, Mario & Pretty Ricky | Chicago | Music - Soul / R & B |
| The Mountain Goats | Chicago | Music - Alternative Rock |
| The Purple Xperience - Tribute to Prince! | St. Charles | Miscellaneous |
| The Righteous Brothers | St. Charles | Music - Rock & Metal |
| The Rising - Tribute to Bruce Springsteen | Evanston | Miscellaneous |
| The Rolling Stones | Chicago | Music - Rock & Metal |
| The Tubes | St. Charles | Music - Rock & Metal |
| The Ultimate Wealth & Achievement Summit with Tony Robbins and Gary Vaynerchuk... | Chicago | Business - Conference |
| The UNICEF Gala Chicago | Chicago | Community - Fundraiser / Benefit |
| The Who | Tinley Park | Music - Rock & Metal |
| The Winter's Tale | Chicago | Performance - Musical |
| Third Eye Blind & Jimmy Eat World | Chicago | Music - Alternative Rock |
| Thomas Rhett, Dustin Lynch & Russell Dickerson | Chicago | Music - Country & Folk |
| Tim Allen | Chicago | Performance - Comedic |
| Todd Snider | Chicago | Music - Rock & Metal |
| Tom Segura | Chicago | Performance - Comedic |
| Train, Goo Goo Dolls & Allen Stone | Tinley Park | Music - Rock & Metal |
| Trevor Noah | Chicago | Performance - Comedic |
| Turnover, Turnstile & Reptaliens | Chicago | Music - Alternative Rock |
| Tusk - Tribute to Fleetwood Mac | Joliet | Music - Rock & Metal |
| Uli Jon Roth | St. Charles | Music - Rock & Metal |
| Valerie June | Chicago | Music - Soul / R & B |
| Van Morrison | Chicago | Music - Rock & Metal |
| Veil of Maya | Chicago | Music - Alternative Rock |
| Victor Manuelle | Rosemont | Music - Latin |
| War | St. Charles | Music - Soul / R & B |
| Warrant | St. Charles | Music - Rock & Metal |
| Why Don't We | Rosemont | Music - Rock & Metal |
| Wilderness Walk | Chicago | Educational - Science & Nature |
| Willow Chicago Weekend Service | Chicago | Community - Religious |
| Wizard World Comic Con: Chicago - Sunday | Rosemont | Miscellaneous |
| Wizard World Comic Con: Chicago - Thursday | Rosemont | Miscellaneous |
| Yacht Rock Revue | Chicago | Music - Rock & Metal |
| Yann Tiersen | Chicago | Arts - Concerts |
| Yheti | Chicago | Music - Electronic & Trance |
| Yngwie Malmsteen | St. Charles | Music - Rock & Metal |
| You're A Good Man Charlie Brown | Oakbrook Terrace | Performance - Musical |
| Zoe Keating | Chicago | Arts - Concerts |
