Chicago, the Windy City, can be mighty cold in the fall, but when you have someone to cuddle with, you might not even notice the breeze. Many people think spring is the best time to fall in love, but there is something very romantic about Chicago in the fall: the radiant hues of the leaves, the cool breeze, the smell of pumpkin and walnuts wafting out of every coffee shop. If you don’t believe me, try one of these awesome fall date ideas, sure to bring out the best of the season.

Go Apple Picking

Sure, you went apple picking when you were a kid, but somehow apple picking is much more fun when you go as a grown up. Honey Hill Orchard boasts over 2,100 apple trees, a perfect place to get lost, stroll, wander through the trees hand in hand and, of course, pick some apples! Just an hour and a half out of Chicago you will feel like you have truly stepped into the country.

Make Your Own Wine

While you may not be stomping on grapes like they did in the Italian countryside, Bev-Art Brewer and Winemaking Supply offers you the chance to make your own wine from start to finish. The winemaking class includes step-by-step instructions on how to make a variety of wines from Chardonnay to Cabernet. This date is sure to give you something to talk about - and something to drink when you bottle your wine later on.

Get Spooked

If you’re both horror film buffs (or even if you’re not), nothing will bring you closer together than watching a few scary films. In September, the Chicago Horror Film Festival delivers a delightful variety of dread, guts, and gore. Book your tickets early to save time and money.

Go on a Scavenger Hunt

What’s the best way to bring out the best in your date? Get competitive. It’s the best way to see if you can work with each other, instead of against. The Amazing Scavenger Hunt turns Chicago into a giant chess board, with you making all the moves. Compete together in this interactive scavenger hunt around the city of Chicago by answering trivia questions and discovering all the famous landmarks along the way.

couple map planning
couple map planning

Bottle and Bottega

Getting messy, drinking wine, and creating a work of art with your hot date. Sounds swell to us. Bottle and Bottega is a painting and wine class that gives you the step by step tools to create a Picasso piece of your own while enjoying a nice bottle of wine. It’s a brilliant first date spot (if you stay together, you can use the painting as keepsake) or even an anytime date spot.

For more great date night ideas, follow Cupid’s Cronies Chicago Matchmaker on Facebook and Twitter.