September 2019
- Vintage CTA cars are returning to the Loop for Customer Appreciation Day
- Sequoyah Murray + Loona Dae + Cae Monae
- Bad Femme: Halloween Double Feature
- JPEGMAFIA + Butch Dawson
- “Photography + Folk Art: Looking for America in the 1930s”
- “Third Realm”
- 11 questions with a real-life Michelin inspector
- Delilah's Oktoberfest and Pumpkin Beer Tasting
- The Big Quiet
- Griz + The Funk Hunters
- The New Pornographers + Lady Lamb
- 25 Chicago restaurants earn Michelin stars for 2020, including three new omakases
- Here’s every single Millennium Park holiday event that you can look forward to this winter
- Time Out Market Chicago announces an event series with Erick Williams and a hidden tiki speakeasy
- The Purple Pig - Time Out Market Chicago
- The Art of Pizza - Time Out Market Chicago
- Thai Dang - Time Out Market Chicago
- Mini Mott - Time Out Market Chicago
- Urbanbelly
- John Manion - Time Out Market Chicago
- FARE - Time Out Market Chicago
- Pretty Cool - Time Out Market Chicago
- Lost Larson - Time Out Market Chicago
- A search for the best Negroni in Chicago
- Spooky Pooch Parade
- RuPaul’s Drag Race Werq the World Tour
- Disney in Concert: Tim Burton's The Nightmare Before Christmas
- Chicagoans can have recipes from the Bon Appétit test kitchen delivered straight to their door
- Lyric Halloween Masquerade
- ACE Comic Con Midwest
- The King’s Speech
- Fifth Third Arena
- Thunder on Southport Motorcycle Rally
- Lazy Bird
- The Massacre Horror Movie Marathon
- We sent two Chicagoans on a blind date in Wicker Park—here’s how it went
- The Great Leap
- Eyeconic (West Loop)
- Eyeconic (Bucktown)
- Wonderful Weekends Chicago
- Black Mountain + Dommengang + Majeure
- Savage Love Live
- Chicago Humanities Festival: Power
- Spooky Zoo
- Red Bull Music Festival Chicago is back with Lupe Fiasco, Saba, Jamila Woods and more local acts
- Charli XCX + Allie X
- The Chainsmokers + 5 Seconds of Summer + Lennon Stella
- 54 Chicago restaurants earn Bib Gourmands for 2020
- Bon Iver + Feist
- Joanna Newsom
- Ghostly 20: Tobacco + Shigeto + Drama + Steve Hauschildt + SV4
- Dana H.
- The Catcade Carnival
- The Moonlight Parade
- ‘Friends’ 25th Anniversary: The One in the Windy City
- Chicago Architecture Biennial
- “Wesley Willis: City of Many Dreams”
- Matthew Rachman Gallery
- Adler After Dark
- Metroberfest
- YAS! Fest: Youth Arts Showcase
- The best attractions and things to do in Pilsen
- Pilsen Vintage and Thrift
- How Garrett Popcorn became an indisputable Chicago institution
- Knee Deep Vintage
- Geometry of Light
- Belli's Local Foods
- Whoa! A Good Burger pop-up restaurant is coming to Chicago in 2020
- Chicago Ideas Week
- Score free (and cheap!) popcorn during Garrett’s 70th anniversary celebration
- Welcome to the Jungle Homebrew Competition and Festival
- Bacon and Beer Classic
- ChiSox Craft Beer Fest
- Hot Chip + Holy Fuck
- Rickmobile Chicago
- The Band’s Visit
- Chicago Rare and Wild Beer Fest
- Hoptoberversary
- Wine Riot
- Nick Offerman
- Dessert Fest at the Zoo
- Lakeview East Festival of the Arts
- Chicago Barbecue and Bourbon Festival
- Chicago Karaoke Festival
- The world’s largest Starbucks will debut on Michigan Avenue in November
- Oktoberfest Beer and Pinball Party
- Chugtoberfest
- “Julia Fish: bound by spectrum”
- “Wired to Wear”
- The Barber of Seville
- St. Clair Supper Club
- Swerski's: A Chicago Pop-up Bar for Superfans
- Breakfast For Ina
- BKBDay 10
- Noir City Chicago
- Shapeshift 2019: Bauhaus in Chicago