Chicago’s winters are rough, with several feet of snow coming in every year, so it’s no wonder that the season right before this chill is when the city goes all out!  If you’re ready to visit Chicago in the fall and you want to make the most of your visit: these are all of the outdoor stops you should make! 

The Pumpkin Fun Run

If you’re eager to have a great time running while doing it for a good cause: consider joining the Pumpkin Fun Run!  This annual event is going to be on October 15th this year, offering the chance to all runners and walkers of every age and ability to go on this trail and help raise money for the Forest Preserve District!  A fantastic way to give back to your community. You’ll get to run and meet other locals while supporting an awesome cause.

Casual Market Chicago

Why not shop until you drop?  If you’re looking for new retailers and want to check out some new items you hadn’t considered before: consider stopping by the Casual Market in Chicago!  Open from September 20th to the 23rd; you can shop for casual living, check out new and innovative products, and learn about brands you’ve never heard of before.  This can be a fun day of window shopping or inspiration for a home redesign! 

Couple’s Outdoor Bowling

If you and your significant other need a break from looking at apartments for rent in Chicago, why not go bowling?  Couple’s outdoor bowling in Chicago gives you the chance to have fun in a fall and Halloween-themed event, bowling with the person you care most about.  If you’re single, don’t worry!  This event is also open to friends who want to bowl together; it’s just geared more towards couples, so you can still have fun!  

Couples Stormy Reflections

Bring your own paint and canvas; it’s time to get to work!  Bottle and Bottega will be hosted by Painting With a Twist this year on October 29th from two to four-thirty pm.  This event will include outdoor painting, drinking, chatting, and having fun!  At the end of the day, you’ll get to take home a masterpiece inspired by the holidays and make some awesome friends who share your interests.

TIP Fest

Teens in the Park Fest is a great time for Chicago’s young artists to show off their skills and play to a crowd of locals.  This is a teen and kid-friendly event on October first, from one to five in the evening.  You can ask your teen if they’d like to take part or drop your teens off so they can have fun with kids their own age.  There are snacks, drinks, and multiple performers, so this will be a lot of fun for any high-schooler!  Make sure to pack a water bottle for your kid since it’s a long event.

Chicago Comes to Life in the Fall!

Fall is the best season to visit Chicago!  From the incredible food to the beautiful sites and amazing locals, there’s no reason not to love Chicago.

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