Perfect Girls Weekend In Chicago

February 1, 2016
perfect girls weekend chicago

This weekend, my friend Emily was in town from Milwaukee, which meant an epic girls weekend was in order. We gathered with our friends Sarah and Jackie Friday night for an evening of gossiping and girly drinks. Girls night essentials: Cards Against Humanity, reality television, a blender, a balcony with skyline views.


I love having visitors because it gives me a reason to check off things on my ever expanding Chicago bucket list. I’ve been wanting to explore Pilsen for some time, and a girls weekend was the perfect opportunity. I’ve been a few times before, but usually for a specific event or meal, and hadn’t had the chance to wander around the neighborhood or spend significant time there. After this weekend, I want to move! Such a charming area of Chicago, full of local shops, great restaurants, and no tourists. Well, until they read this post… 😉

We started Saturday morning with brunch at Dusek’s. There was a bit of a wait, so we put our name in and wandered over to Bellis for a snack. Splitting the avocado toast and sipping some energizing juices gave us just the boost we needed to wait for a table without becoming cranky or bored.

Dusek’s is housed in historic Thalia Hall, and the space is gorgeous. I’m in love with the chandeliers and blue walls that give it a classic yet modern vibe. It was hard to choose what to order (story of my life), and in the end we went with the omelet with truffled ricotta, swiss chard, and maitake mushrooms; the challah french toast with apple compote, toasted almonds, brown butter crumble, and maple cream anglaise; and of course the chicken and waffles, which are upgraded from your typical southern deliciousness with fig maple syrup, apricot purée, and foie gras butter. Yum!

Moving on, we wanted to stop at Punch House to share a bowl of their amazing punches, but sadly they don’t open until 6pm. Apparently not everyone was as excited about day drinking as we were. Either way, you should definitely check it out at night sometime.

Next door, we window shopped at Lost Girls Vintage, one of my favorite places in Pilsen.  If you’re coming from across Chicago, make sure to have a way to carry everything you will inevitably buy home.

This girls weekend was about eating not shopping, so we moved on to Chocolat Uzma Sharif, where we oohed and aahed over the beautiful truffles and packaging for about 10 minutes before finally ordering. They have actual candied rose petals! So pretty! Once we did finally order, we were in chocolate coma heaven. The sipping chocolate is so decadent and delicious. It’s not too sweet, which is perfect, but it is filling, so you can probably share. (We didn’t and wished we did).

Right next door, BYOB painting at VIP Paints is the perfect way to wrap up the Pilsen chapter of your girls weekend.

Full, happy, and not completely recovered from the night before, we took a break to (attempt to) nap and recharge. Girls weekend was only just getting started.

Reconvening with fresh makeup and heels, we were ready for a night out. Our Uber driver made our night by blasting Out of the Woods for us on the way to The Aviary, where we stood in line and joked with the doorman for about 15 minutes before being let in. (He kept checking in through his headset with a colleague inside also named Emily, which we found endlessly amusing and soon he did too. Maybe one of those ‘you had to be there’ stories).

If you’ve never been to The Aviary, it’s a Chicago must-do, and really I think it fits on a must-do cocktail experience list for the entire world.  “Where cocktails and service are given the same attention to detail as a four-star restaurant; where bartenders are trained as chefs,” reads part of the first sentence on their website. In the past, one of there bartenders has been named ‘Best Bartender In the World.’ Heading in, you walk past the bar, which resembles a restaurant kitchen on a busy night mixed with a chemistry lab. We settled into plush seats and watched the science experiment-like drinks served around us before ordering our own. Once served, each drink had its own explanation. Mine was a creamy cocktail with flavored fruit and nutmeg ice disks and a special straw that doubled as an ice crusher. Sarah’s had rum balls that exploded in your mouth and reminded us of bubble tea, Emily’s looked like a volcano and had a hibiscus ice slab, and Jackie’s had orange ice cubes that changed the flavor as she drank. By far one of the coolest places you can go in Chicago, either on a date or for a girls night out. Either get there early to avoid a long line, or make a reservation. (I realllly wish I had photos, but it was so dark inside that the few I have are terrible, and I was too consumed by the drink explanations to remember to take more!).

Next, we slurped noodles at Ramen San, drank and danced at Hubbard Inn, sang karaoke at Local 22, and somehow ended up at VIP’s (not sure I recommend that last one). Overall a full night of adventure and plenty of stories for the next day.

girls night chicago ideas


By Sunday we were exhausted and wanted to spend the day in bed, but that’s what Sundays are for. I watched the entirety of season 4 of Girls and ordered takeout. Perfect.

If you live in or are visiting Chicago, I hope you check out some of these spots! For help planning your own perfect girls weekend, check out my trip planning page or email me at


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