Five Must-Do Activities in Chicago This Fall

While the official start of fall came yesterday, I’ve already accepted that summer has come and gone. Since fall tends to be a short season here in Chicago, I like to make the most out of every single day. A few weeks ago after some on and off travel, I realized that I missed Chicago. While that might sound weird, it’s true. I love this city, and I love that the city is always bustling and buzzing with a variety of activities that happen every single day.

So this fall season, I’ve made it my mission to start dating the city of Chicago. Each weekend for the next few weeks (honestly until the first snow, because all bets are off when the snow starts to hit) I plan to check out a new part of the city; hopefully taking in an activity or two. Thankfully a new to Chicago website, Vimbly, makes it easy to plan things and pay for them ahead of time. This super convenient website shows you all the great events happening throughout the city in the upcoming weeks. Interested in a helicopter ride? A food tour? Trust me, Vimbly’s got ya covered.

So what are my top 5 activities that you should check out this fall? Well take a look below and join in on the conversation. I would love to know if there are any upcoming events in the area that I should check out!

:: Chicago Food Tour – Bucktown & Wicker Park ::

A few weeks ago, Rachel and I brought along some friends to spend our Saturday on a Bucktown & Wicker Park Food Tour. Let me tell you guys, food tours are amazing! Over the course of 3 hours, I learned more about the city of Chicago and the two neighborhoods then I ever thought was possible. The food was delicious as well, with stops at George’s Hot Dogs (for a classic Chicago style hot dog), Hot Chocolate (for a iced hot chocolate), The Goddess & Grocer (for their famous kale salad), Piece Pizza (for a classic pie), Sultan’s Market (falafel so good), and Stan’s Donuts (gluttonous, I know).

Just because you’ve been living in Chicago for year doesn’t mean there isn’t stuff to learn! So go out there and check out a few of their other food tours, including Chinatown & Lincoln Park.

:: Helicopter Ride of Chicago ::

This was one of the first activities that pops up when you log onto Vimbly and whoa baby what an experience this would be. Chicago has some of the best skyline’s in the world, and I personally can’t stop taking photos of it. A helicopter ride to see all of Chicago would be one totally unique experience. For those of your adventurous couples, this would be a great date night activity!

:: Aerial Silks & Trapeze Class ::

Fun Fact: That’s me in the photo hanging on for dear life during my trapeze lesson. I’ll be honest, the entire experience was exhilarating, fun, and exhausting all at the same time. It looks so easy when you see the professionals do it, but man is it a ton of hard work. Having some upper body strength is key to lasting through this class.

The Chicago chapter of the Trapeze School of New York hosts a variety of trapeze (indoor & outdoor) classes as well as Aerial Silks. I recently started silks class and it’s equally hard and fun – I even learned a pretty neat trick in my first class.

Looking for a new workout or just a fun weekend activity – I give the TSNY a huge thumbs up!

:: Distillery Tour – Lagunitas, Buckie Down & 5 Rabbit ::

Boozing on a the weekend more your speed? Well you are in luck! The Chicago distillery tour is the hottest ticket in town and visits some established and new distilleries and breweries that call Chicago home. A great way to get to know some less than well known parts of the city as well as sample a few amazing beers during your tour, this one is high on my list.

Looking for a great way to get your guy out and about on the weekend? I think this tour will be right up his alley.

:: Devil & The White City Tour :: 

Calling all book worms, things just got interesting! For those of you who have read Devil in the White City (if you haven’t, seriously go do it now) the entire book was based on The World’s Fair that took place in Chicago. The book does a wonderful job describing a variety of places around the city of Chicago and this tour takes you up close and personal with many of the locations discussed in the book. This is a great way to live a book, before the movie comes along and ruins it.

So what are you most looking forward to doing this fall season?!

:: Photography by Rachel Geeser  & Monica Modzelewski ::

This post was sponsored by Vimbly, as always all my opinions are my own.