My "anti-tourist" Chicago activity guide

Ankle booties: c/o indigo rd, available at Francesca’s (stay tuned for an outfit photo coming with these coming soon, too!) // Skirt: Nordstrom (on sale for $23! This one is identical, and I’m OBSESSED with this navy asymmetrical suede number, too! // Blouse: Topshop at Nordstrom (also comes in white–size tip: runs small, but if you prefer a more fitted look, order your regular size. For a looser size, go up!I’m wearing a size 2, which fits like a 0.) If you love this color, you’ll also love this ruffle top that I’ve got my eye on, and also love this wrap-front version in the same color! // Clutch: Vintage, but I love this Rebecca Minkoff version in the same color (I have it in black!)

Sure, we all know about Navy Pier, The Hancock Building and the Sears (locals refuse to acknowledge the “Willis” name change) Tower SkyDeck–all good things to experience once in a lifetime, but Chicago is even more magical when you get off the beaten path.

Today I’m so excited to partner with indigo rd (you first saw them here!) to bring you part two of my three-part Chicago themed series, where I share my favorite spots to shop, play, and eat in the windy city! If you’re looking to experience Chi-town like a local (or if you just really like cute fall outfits) you’re going to love this post!

Here are some of my can’t-miss activities:

The Flatiron Building

One of my favorite buildings in the city is the Flatiron Arts Building (pictured here!) Not only is it cool to look at, but it’s one of the most unique things you’ll ever find in the city. The flat iron is essentially a maze of studios home to local artists, which is free and open to the public. I first stumbled upon it exploring Wicker Park with my mom, and we had so much fun meeting artists, getting to know them, and watching what they were working on. They also hold “First Friday” events every month, which serve as an “open house” of sorts.

IO Theatre

Of course you’ve heard of Second City–everyone has–which is unreal (and I’d totally recommend it) but did you know the source that feeds all those amazing comedians into Second City? IO Theatre! If you want a ton of fun without the Second City price tag, IO is definitely worth a trip!

Bike the 606

One of my new favorite things about being a Wicker Park resident–easy access to the 606. Also known as the Bloomingdale Trail, this is a brand new bike & walking path that connects Chicago’s coolest western neighborhoods–Bucktown, Wicker Park, Logan Square, and Humboldt Park. It’s a great way to get around and there are tons of really cool bars and restaurants along the way. (Sweet Rice has some of the best ever Thai food and Scofflaw is one of my favorite cocktail bars in the city!)

Old-School Jazz Clubs

Chicago is home to some pretty fun jazz clubs–the Green Mill being the most famous of them all, and believed to be the oldest running jazz club in the country. An old Capone hangout, it’s also rumored to have underground tunnels that mobsters used to frequent to get in and out of the club. It’s still known as the best place to catch some live jazz. If you aren’t up for the hike up North, Andy’s Jazz Club in River North also has a lot of history and is a great time!

Local Breweries

Quite a few local breweries have cropped up in Chicago in recent years–the most famous is Lagunitas, which has a massive brewery on the Near West Side, it has a great bar and offers tours! Revolution Brewing near Logan Square has an awesome taproom and they brew some of my favorite beer! (Rosa is my go-to in the summer, and Neal loves their IPA.) I’ve heard great things about Hopwell as well, and it’s on my list to check out!

Explore Pilsen

Yes, not exactly a specific “activity” per say, but Pilsen is one of the coolest up and coming neighborhoods that tourists virtually know nothing about. Not only is it home to the best Mexican food in Chicago (Los Comales!) but it has tons of artists (they also have “first friday” art walk events!) and my favorite bar destination–Thalia Hall, which has 3 bars in one (You definitely need to check out all of them–Dusek’s, Punch House, and Tack Room!) in addition to being a concert venue.

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Okay, so we talked local activities, now onto this outfit! I love lovee the color of these suede booties along with the lace-up detail in the back. The heel and almond toe is also so flattering–plus, they’re super comfortable! I went for a monochrome look with this pretty pink feminine blouse and a wine-hued mini skirt. (Perfect for a night out to one of Chicago’s Jazz Clubs mentioned above!)

Speaking of what to wear–just for the record, Chicago is probably one of the easiest cities to visit when it comes to dress code (okay, yes, I admit you DO need a lot of layers if you visit in the winter) because you can get away with wearing jeans pretty much anywhere, but we also love a good excuse to dress up from time to time. Essentially–it’s pretty hard to be overdressed or underdressed, which is why versatile staples like these are such wardrobe heroes! (Gotta love the Midwest, right?)