Oct 12, 2023 - Things to Do

Chicago weekend events: Night of 1,000 Jack-o'-Lanterns, Wine Rival and more

A pumpkin at the 2022 Night of 1,000 Jack-o'-Lanterns. Photo: Courtesy of Chicago Botanic Garden

Walk among artistically carved pumpkins, cheer on the Bulls or try the best pizza in town.

  • Here's what's happening in Chicago this weekend.

🎃 1. Night of 1,000 Jack-o'-Lanterns

Spend a night with 1,000 glowing, hand-carved pumpkins while sipping your favorite fall drink at Night of 1,000 Jack-o'-Lanterns in Glencoe.

What's happening: Guests will be able to walk among the jack-o'-lanterns, attend carving demonstrations, interact with costumed entertainers and enjoy seasonal food and drinks like apple cider donuts and hot chocolate.

Why it matters: This is your opportunity to see artist-carved pumpkins with designs including monster faces, aliens, Día de los Muertos and movies filmed in Illinois.

When: 6–10:30pm Thursday–Sunday and Oct. 18–22

Location: Chicago Botanic Garden

Cost: $21 per adult and $14 per child (3–12) for members, $23 per adult and $16 per child for non-members

Of note: Advance tickets are sold out, but you can buy tickets on site.

🍕 2. Chicago Pizza Summit

  • Not to be confused with Pizza City Fest, the Pizza Summit will include a surprise keynote speaker, photo booths, a tattoo parlor, music, pop-up art and a pizza-themed fashion competition.
  • Participating restaurants include Professor Pizza, Gino's East, Five Star and Paper Plane.
  • When: Session 1 is from 11am–2pm Sunday; session 2 is from 3–6pm
  • Where: Royal Palms
  • Cost: $50 for anyone under 21 for session 1; $65 for anyone 21+ for sessions 1 and 2.

🏀 3. Bulls preseason home opener

  • The Bulls are set to host the reigning NBA champions, the Denver Nuggets, at the United Center at 7pm Thursday. It's the preseason, so the starters will only play for 15–20 minutes. Tickets start at $29.

🍷 4. Wine Rival

  • "The Super Bowl of Wine" returns to Venue West from 5–9:30pm Sunday. Attendees will be able to sample from dozens of wineries and watch a blind wine tasting competition. There will also be a DJ booth, finger foods, a spa lounge and a full bar with cocktails and beer. Tickets are $89.25.

🇲🇽 5. Lit & Luz

  • This weeklong cross-cultural and bilingual art and literature festival brings together artists and writers from Mexico and Chicago for free programming, including lectures, performances and workshops. The festival kicks off Friday with an exhibition at the Chicago Art Department from 6–10pm. Full festival schedule.
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