October in Chicago: 5 Things to do

October in Chicago is our favorite time of the year. The weather is that perfect balance between cool autumn breezes and sunny skies. And along with pumpkins, vibrant foliage, and rich palates, comes many new activities that the city has to offer. Check out these fun spots with family and friends before the snow comes along!


Honey Hill Orchard

Where: 11747 Waterman Rd, Waterman, IL 60556

Located an hour’s drive from downtown Chicago, Honey Hill Orchard is a local fan favorite, offering apple and pumpkin picking,  a bakery stocked with delicious treats (cider donuts are a must try!), and a hay bale maze and a petting zoo for kids. Admission and all activities are free too. As an added bonus, the farm is located only 5 miles away from Shabbona Lake State Park, so you can head there for a picnic or bonfire afterward.



Where: 12 S. Michigan Avenue, Chicago, IL 60603

Cindy’s rooftop terrace offers a great view of the Chicago skyline and the beautiful colors of Millennium Park. Cindy’s also has an innovative selection of alcoholic drinks, including creations like Western Cape (A peachy version of a Moscow Mule with South African rooibos, lavender, rosehips and dried elderberries) and A Kick in the Daisy (A watermelon Margarita with hints of marshmallow giving way to a lingering burn). For those of you working in the Loop, Cindy’s is a great place to stop by after work and kick back and relax.


Chicago Botanic Garden

Where: 1000 Lake Cook Rd, Glencoe, IL 60022

You can also head up north to the Chicago Botanic Garden for an immersive experience in the fall foliage and take quality photographs. It is located on 385 acres and showcases over 27 different garden varieties. The Chicago Botanic Garden provides guided learning experiences on the weekends such as Japanese flower arranging, horicultural shows, and flower sales. This year, they are also hosting the Night of 1,000 Jack-o’-Lanterns, which will feature more than 1,000 hand-carved pumpkins—some as large as 150 pounds.


Haunted Halloween Ball

Where: 520 S Michigan Ave, Chicago, IL 60605

The Congress Plaza Hotel is said to be one of the most haunted places in Chicago. The hotel was built in 1893 to house visitors of the Columbian Expo, and it seems that some guests have never left and continue to roam its hallways, causing mischief and mayhem. There is no better place for a spooky Halloween ball. The Haunted Halloween Ball will be featuring DJ Rock City, DJ Torio, and others. There will also be a costume contest and the top 3 contestants will be awarded $3000 in cash and prizes. Early-bird general admission tickets are $20. They also offer table reservation packages that include two premium bottles, eight party tickets, and reserved seating, starting at $750. For those who dare to stay overnight, a special Halloween weekend hotel room rate of $163 is available for October 28th thru October 30th.


Wine Tasting

Where: The Promontory, 5311 South Lake Park Ave West, Chicago, IL 60615

Love Cork Screw wines is an up-and-coming phenomenon started by respected wine connoisseur Chrishon Lampley. Each of their different wines has a unique personality and story behind it. Five to Nine has also collaborated with Love Cork Screw wines during our “Appy Hours,” and they have received great reviews from our members. Love Cork Screw will be holding a wine and networking event at the Promontory in Hyde Park on 10/25, and it’s free!

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