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What to do (and wear!) this Labor Day!

Sep 3, 2015


Top: c/o Vineyard Vines // Pants: Loft (old) Similar // Bracelets: J.Crew and Busywrist // Sandals: Madewell (old) Similar // Lips: Younique Lip Stain in Skittish 

Labor Day is always a special weekend in Chicago–there’s so much going on, your options are literally ENDLESS, no matter what type of three day vacay you’re planning on having–entertaining guests, or just taking it easy.

As you guys may have seen on Instagram, my mom is in town this weekend! We’re taking a mini road trip to visit some family friends in Lexington, KY and then heading to Neal’s family lake house for the weekend! 

Although I won’t be in the city for the holiday, I’ve heard about TOO many great things going on not to share. 

And for those of you who don’t live in Chicago, I thought this could still serve as some Labor Day outfit inspiration 😉 

Things to do: 


Chicago Jazz Festival 

What’s better than a FREE live jazz concert in Chicago’s most beautiful park? I’ve never attended this, but it’s always been on my bucket list! If you go, please tell me how it is! I’ve heard nothing but great things! 


Glamping at Camp Dana 

Starting at $1200, you can relive your childhood glory days with two nights at Camp Dana! Enjoy a great dinner for two at the hotel’s restaurant, roast your own s’more treats each night, a massage for two, arts & crafts–and the kicker? There’s a TIPI in your room!! 

The arts & crafts portion also includes some DIY masks or scrubs from the award winning spa at dana and a mixology class at the hotel’s rooftop lounge, Vertigo, plus a cooking class on property.

I had a chance to preview Camp Dana a couple weeks ago and it was the best night ever! If you’re ever looking for a stay cation, you can’t find one better than this! 


Cirque du Soleil

Funny story, one time Neal surprised me with a date night at “Cirque de Shanghai” at Navy Pier. We were both so excited, and then we got there only to find it was in no way affiliated with Cirque du Soleil whatsoever. It was so terrible that it was actually hysterical. We sat there cracking up the whole time, in the outdoor amphitheater roasting and sweating in 100 degrees.

Then we went to Margaritaville and Neal spilled my Strawberry Daquiri on his white shorts. All in all, it was a date night for the record books and actually one of my favorites looking back.

However, we never made it to the real Cirque du Soleil. Here’s hoping we do sometime soon, seeing as now they are in town–but nonetheless, it will make an excellent Labor Day activity! 


Taste of Polonia

If you have a thing for pierogi’s and polka (I mean, really, who doesn’t?) this is going to be your jam. 


Oak Street Beach 

Pack your cooler and get your final fix of the beach before it closes down for the season! If you don’t, you’re going to be kicking yourself in January, just sayin’. 


Pilsen Community Market

I’ve always wanted to check out the community farmer’s market in Pilsen! Pop by this weekend, and then do some awesome vintage shopping and eat some (obviously) amazing Mexican cuisine! 


Bubbly-Q at City Winery

City Winery is throwing their annual Labor Day bash with plenty of BBQ and champagne (best combo ever?) from 2-9pm on Monday! $15 gets you admission, and some wine tasting! For food, expect a pig roast, and other tasty bites. 
Road trip to Chicago Premium Outlets

I just took a trip to the outlets this week (more on that soon!) and you guys, you wouldn’t even be able to tell this was an outlet mall. It was so clean, organized, and had the cutest stuff! There will be deals up to 70% off already discounted items. If you’re looking for a daytime activity, this would definitely be one to put on your list! Plus, they offer a free shuttle from downtown! 


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What to wear: 


I’ll be living in things like chambray tops, white denim, and sandals this weekend. 

(Because summer isn’t over yet, remember? I, like Maya, am a full proponent of white pants AFTER Labor Day.) 

I’m not going to put away this Vineyard Vines top until it starts SNOWING. 

Okay, maybe that’s a bit dramatic, but I’m for sure wearing it through the fall. 


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What are you up to for Labor Day? 

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