Fall Activities in Chicago

Happy (almost) October! Autumn has officially arrived — a little quicker than I anticipated… I’m sure you feel the same — however, I am more than ready to start checking activities off my list before the last leaf falls. See my list of activities below that vary between cozy date night spots, to apple picking spots, to haunted boat tours; perfect to do with a group of friends, or your significant other.  🍁


  • Chicago Haunted River Tours 
    • Through the month of October, Seadog boat tours provides haunted a boat tour Friday – Sunday — perfect for date night!
  • Loews Hotel 3rd Annual Harvest Fest
    • Complete with pumpkin patch, carnival games, entertainment, and biergärten, Harvest Fest will take place on Saturday, October 14 from 11 a.m. – 5 p.m & it’s free!
  • Pumpkin Patch for Pumpkin Picking 
    • Try Goebbert’s Pumpkin Farm
  • A Hot Chocolate Walk Viewing Fall Foliage
    • Grab a Starbucks hot chocolate and head for a walk through the Alfred Caldwell Lily Pool
  • Apple Picking 
    • Make a day trip out to Ziegler’s Apple Orchard to pick some fresh apples. Don’t forget to buy some apple and cinnamon donuts!
  • A Day trip to Long Grove for Apple Fest 
    • The last day for Apple Fest is September 24th — make the day trip and make sure you pick up some chocolate covered strawberries at the confectionery while you’re there!
  • A Cozy Date Night at Geja’s 
    • How does fondue sitting next to a fire sound to you?
  • Oktoberfest in Evanston 
    • You don’t need to go all the way to Germany to enjoy Oktoberfest; you don’t even have to go all the way to Wisconsin! Evanston is holding their Oktoberfest October 15th.

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