If you had asked me at 5 what I wanted to be when I grew up, I would have said, “A lawyer or a Soul Train dancer.” I missed the soul train, but I did make it through law school with a few pieces of my soul intact. I rehab the other pieces by blogging about style, traveling, and relocating my life at the drop of a hat.

Some people advise me to pick a career, pick a city, and stop dodging my student loan company’s incessant calls — but I’m still saying “YOLO” without a hint of irony.

Right now, I’m in Chicago. I’ve lived here for over a year now, but there’s still an astounding amount of city-stuff I have yet to experience. Recently, I had the opportunity to partner with Gilt and Gilt City to check out a few of the city’s hot spots over a weekend, all of which offered luxe deals at budget-friendly prices.

The Fun and Leisure Part

I started my weekend off with an aerial fitness class at AirFitNow. Let me explain why this is weird: With the exception of the very occasional 50-minute class, my workout routine consists of walking back and forth between the couch and the mailbox. I’d like to work out more, but my days are usually packed to the brim with other important things, like Netflix and obsessively left-swiping on Tinder.

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I’ve literally bungee-jumped from a bridge in South Africa, and yet — a mere two feet off the ground — I felt my stomach wrap itself around my throat and hang on for dear life when we were instructed to flip upside down. But with a little coaxing and a whole lot of prayer, I did manage to invert myself, and it was fun as hell! (The same is true of bungee jumping, for the record.)

Saturday night consisted of a paint-and-wine class at Pinot’s Palette in the West Loop. When I glimpsed the intricate painting we were going to be attempting, I had more than half a mind to grab my purse and hightail it out of there. However, after a few glasses of rosé, I had somehow convinced myself that I’m destined for a career in the arts. As it turns out, “beer goggles” apply even outside of dark nightclubs.

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The following morning, I challenged myself to a workout class at Kick@55, a place that did, in fact, kick my ass. If your goal is to go from Winnie the Pooh to Teyana Taylor overnight, this class is definitely for you. As for me, I’m going to go join a gym for a year, get my physical (and spiritual) life together, and then come back for another go.

The Fashion Part

I may have experienced all manner of pain during my fitness classes, but at least I was able to do so in style and comfort. Gilt’s array of activewear proved to be as practical as it was “on trend,” offering me at least a little consolation during my workout travails.

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Being from Georgia, I had never understood the appeal of “sweater weather.” Now that I’ve lived in northern climates, I’ve been warming up to fall fashion. I was eager to style some of Gilt’s cozy autumn pieces, like this 3.1 Philip Lim sweater, which I love:

It should be mandatory for everyone to own a good chunky sweater, especially if it resembles a glamorous mop. The lack of sleeves makes this the perfect transition piece — and, paired with a simple pair of J Brand boyfriend jeans and kick-ass platforms from Charlotte Olympia, it became my new favorite fall look.

The Food Part

Dinner on Friday night took place at the Red Door Kitchen & Bar, a gastropub in Bucktown. The low-key neighborhood vibe and cute patio charmed me immediately — but the greatest thing, hands down, was the mac and cheese. To borrow a line from Drake, BEST I EVER HAD. And I say this as a black woman who was raised in the South and introduced to soul food practically at birth.

On Sunday, I headed over to the Ukrainian Village/West Town area to stuff my face at the Rookery. The restaurant truly felt like home from the minute I walked in, with its welcoming staff and vibrant décor. On top of all of that, the food was phenomenal: The chili shrimp came with pork rinds for crying out loud, an unexpected match made in heaven. Followed by short ribs, fries, and a decadent ice-cream sandwich, it seems like my next session at Kick@55 will be just as painful as the last.

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All in all, my weekend was lit: I saw parts of Chicago that I had only been peripherally aware of, spent the entire time dressed to the nines, and renewed my desire to keep exploring my city. Moreover, I was floored that all of these experiences came from the same site — and at prices that would appeal to any fellow student loan debt–saddled millennial. Seriously, try Gilt.

Blake Von D is a lawyer and blogger living in Chicago.

This post is a sponsored collaboration between Gilt and Studio@Gawker.

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