January 2023
- Scratch Goods
- Dolci Amori
- WNDR Museum
- Puttery
- Fall in love with Time Out Market Chicago's Valentine's Day cocktails
- Mavis Staples
- Fika Fest
- The Negro Motorist Green Book
- MCA x Black x Art
- Lantern Festival Celebration
- Vino Camp: An Immersive Wine Experience
- Get listed on Time Out
- How to pitch stories to Time Out Chicago
- A Taylor Swift-themed breakup bar is popping up in the West Loop
- Winter Brew 2023
- Bad Blood: A Taylor-Themed Heartbreak Bar
- Donut Fest Chicago Burbs
- University of Chicago Folk Festival
- Architecture & Design Film Festival
- Physician Magician
- Chicago Auto Show
- Demera Ethiopian Restaurant is headed to Time Out Market Chicago
- Everything you need to know about recreational weed in Chicago
- Ice Cube
- National Geographic Live – Greenwood: A Century of Resilience
- 13 of the best new LGBTQ+ events in Chicago
- How to get tickets to see Madonna in Chicago this summer
- Take a look inside the Willis Tower's new live-fire restaurant
- Brick Fest Live
- Chicago Vintage Furniture Market
- Future and Friends
- PAWS Chicago Pup Pop-Up
- Adler at Night
- Fashion for Freedom
- WNDR After Dark: Invade the WNDRcade
- Chicago
- Lucido's Tacos
- Big Star Mariscos
- Martin Luther King Jr. Day events in Chicago
- How to see the green comet in Chicago
- LUSH Flower Bar
- InFlorEscence
- Campo Santo
- This new restaurant hosts Chicago’s only Champagne wine pairing experience
- MLK Day 2023: South Side Stories
- Martin Luther King Commemoration Celebration
- Cats (Chicago Theatre Week)
- Les Misérables (Chicago Theatre Week)
- Anna Karenina (Chicago Theatre Week)
- Drunk Shakespeare (Chicago Theatre Week)
- The Infinite Wrench (Chicago Theatre Week)
- Wuthering Heights (Chicago Theatre Week)
- Blue Man Group (Chicago Theatre Week)
- Radial Gradient (Chicago Theatre Week)
- The Forge Fat Tire Race
- Flosstradamus
- Loud Luxury
- Made in Eataly Taste-Around
- Chicago Royal Princess Ball
- Dinner & a Movie
- Harry Potter and the Sorcerer's Stone in Concert
- Chicago Boat Show
- Icicle Picnic: Journey for the Sun
- The 10 most romantic speakeasies in Chicago
- 5 new speakeasies in Chicago worth a visit
- Warm up with these delicious winter rum cocktails in Chicago
- Free Monday at the Empty Bottle
- How to spend 12 hours in Chicago
- Winter Wellness Fest
- Brews and Bad Movies