🎃🍂 Chicago’s Most Festive Fall & Holiday Events Are Here! 🍹🎄

Posted on October 06, 2025

• 🍷 October 18 – Chicago Wine Fest @ Hubbard Inn
  This is your chance to sample 35+ wines in one relaxing afternoon. Enjoy curated tastings, cheese & charcuterie pairings, and live music in the beautiful Hubbard Inn space. Location: Hubbard Inn. Highlights: 35+ wines, gourmet pairings, live tunes.
  Get Tickets & Details
• ☕ October 25 – Espresso Martini Fest
  Celebrate the legendary Espresso Martini cocktail at this themed event featuring 15+ signature tastings, creative spins from participating bars, and DJ music to keep the vibe energized. Participating bars will serve their own riffs using espresso, cold brew liqueur, creative spirits, and garnish infusions. Location: Hubbard Inn.
  Get Tickets & Details
• 🎅 December 13 – Godfrey Holiday Cocktail Fest
  Whether you’re a Buddy the Elf or more of an Ebenezer Scrooge, you’re sure to find a cocktail that tickles your holiday fancy at this one-of-a-kind event in River North! It’s the most wonderful time of the year, so spend it laughing, singing, and having fun all while drinking ALL the drinks. Location: IO Godfrey Rooftop, River North.
  Get Tickets & Details
• ❄️ All Winter Long – Holiday Pop-Up Bar Crawl → Christkindlmarket (Wrigleyville Wonderland)
  This seasonal pop-up crawl weaves through holiday-themed bars heading toward the iconic Wrigleyville Christkindlmarket. Expect twinkling lights, themed cocktails, and immersive décor along the route. Location: Wrigleyville, ending at Christkindlmarket.
  Get Tickets & Details
• 🎄 All Winter Long – Crawl to Christkindlmarket (River North)
  This version of the crawl centers in River North → Christkindlmarket in River North. You’ll hit a curated selection of bars serving holiday cocktails, stop by winter pop-ups, and end at the market itself. Location: River North, ending at Christkindlmarket.
  Get Tickets & Details