October 2023
- Vajra
- Pilsen Gourmet
- Whiskies of the World
- Bye Bye Liver: Chicago's Longest Running Drinking Play!
- Tarot Readings at The Press Room
- Ringling Bros. and Barnum & Bailey Presents The Greatest Show On Earth
- 12 unique habits people pick up after living in Chicago
- Halloween forecast calls for snow in Chicago
- Reverie Nails
- Revive Nails & Co.
- Miniluv Nail Salon
- LO Spa & Nails
- Top Coat Nail Spa
- Polish & Pour
- Guinness Open Gate Brewery transcends the traditional Irish pub
- The best snowboarding and skiing resorts near Chicago
- The best family winter getaways in the Midwest
- Chateau Carbide
- Torchio Pasta Bar
- Chicago is the country's rattiest city for a ninth straight year
- Bronzeville's Fall Festival
- House of TAO
- Dog-O-Ween Costume Contest at Midwest Coast Brewing
- 1989 (Taylor's Version) Album Release Party at Paradise Park
- Running Tour and Q&A with Rebecca Makkai
- Lincoln Park Spooktacular
- Get a free slice of Lou Malnati's pizza on November 7
- Sparkle Light Festival
- A Chicago cocktail destination is one of the world's best bars
- Eight fall dishes you need to try at Time Out Market Chicago
- Chefs on Tour at Time Out Market Chicago
- Hyde Park is one of Time Out's coolest neighborhoods in the world
- Heaven on Seven Pop-Up
- Autism Speaks Walk
- Fall Fest at Pioneer Court
- Frankenstein
- Love Me (Bar)Tender
- Chicago Reader UnGala
- Pinball Expo
- John Mayer
- The 25 best bookstores in Chicago
- Powell's Books Chicago
- Winterland at Gallagher Way
- The best restaurants in Hyde Park, Chicago
- Saucy Porka
- Small Cheval
- You can skip the lines at Christkindlmarket this year
- Halloween at Chicago Athletic Association
- Maman Zari
- The Michelin Guide recommends eight new Chicago Restaurants
- The Zabrecky Hour
- The best things to do indoors in Chicago
- Sushi POP!
- Burning Bush & River Room Fall Fest
- Tacos & Tequila Fest at the Zoo
- Garden of Decay
- A Friday the 13th Literary-Themed Run with Local Author David Jay Collins
- Justice of the Pies
- Japanese Horror Halloween at Izakaya at Momotaro
- Bourbon on Division
- Mark II Lounge
- Time Out Market Chicago celebrates Octoberfest, Halloween, Taylor Swift and more
- The Escape Game
- 3 Little Pigs
- Chicago has once again been named the Best Big City in the U.S.
- Latina Comedy Festival
- Beer Hunt at District Brew Yards
- Live After Death: A Comedy Show at Rosehill Cemetery
- Xtreme Xperience
- Dave Chappelle
- Boozy Book Fair
- An acclaimed Dubai-based chef is headed to Chicago for an exclusive dinner
- Kiara Jones is becoming a star in Chicago's food scene