A Girls Getaway to the Windy City

Hello friends! So it’s been 48 hours since I returned from our girls weekend in Chicago … and I’m still tired! I guess this suburban mama isn’t used to staying up past midnight (and in the case of Saturday night, 3am CT!).

But it was totally and completely worth it.

My friends S and T and I planned this weekend a few months ago to celebrate S’s 40th birthday (a bit belatedly) in Chicago. I arrived around 8pm on Friday (my flight was a little late because our flight attendants got lost on the way to the airport in Boston … seriously) and took the train from O’Hare into the city.

Okay, it’s totally geeky and touristy of me, but the whole train ride all I could think about was that scene from one of my favorite movies, “Adventures in Babysitting,” that involves a knife, two dueling gangs (the Lords of Hell, anyone?) and a bad-ass Elisabeth Shue rocking some awesome hair. (Have no clue what I’m talking about? Click here).

I arrived at our hotel in downtown Chicago, just north of “The Loop,” around 9pm (the girls were already there) and we grabbed dinner nearby at this fun bar/restaurant called Rockit Bar & Grill, where we laughed and chatted and caught up (T and I live in the Boston area; S relocated last fall from Boston to Iowa, where she is originally from), since it had been nearly six months (!) since the three of us had been together.

The next morning, we got up bright and early on an absolutely beautiful Saturday (sunny and temps in the 70s!!!) and put on our comfy clothes with the intention of going for a walk along Lake Shore Drive and sneaking in a little exercise before starting our day. After a quick breakfast at a local Corner Bakery, we decided to purchase tickets for later in the day to the Chicago Architecture River Cruise, at the recommendation of one of my college friends, so we headed a few blocks down to the Chicago River.

Recap of our girls weekend in Chicago! www.keepingmommysane.com

Unfortunately, the 2pm boat tour was full so we decided just to hop on the 10am cruise .The tour guide (a retired architect and docent of the Chicago Architecture Foundation) gave us a true insider’s tour of Chicago without getting into all the cheesy touristy stuff (although it was a little lecture-y at times). Plus, the city’s architecture — and some of the stories behind it — is truly fascinating. I highly recommend it if you’re visiting the city and want a unique tour of the city with incredible views.

 Love the Chicago architecture cruise! www.keepingmommysane.com

After the tour, we decided to continue on with our day, rather than going back to change at the hotel like we originally planned, since it was already 11:30am by that point. I will say, walking around in my friend’s borrowed gym pants, sneakers, no makeup and a dirty ponytail was not quite how I envisioned exploring Chicago, but I admit I was pretty darn comfortable :)

Girls weekend in Chicago! www.keepingmommysane.com

So we walked south about 10 minutes to Millennium Park and the infamous “Bean.” For those not familiar with it, The Bean (or “Cloud Gate,” as it’s formally known) was constructed in the mid-2000s and literally looks like a giant silver bean (and reminds me of a Elsa Peretti necklace I had many moons ago).

Girls weekend in Chicago! www.keepingmommysane.com

Just past the park is the famed Art Institute of Chicago, which we knew we had to check out, even for a little while.

Art Institute Chicago

We didn’t get to explore the museum too thoroughly (we were all pretty famished by this point), but I did get to see the infamous American Gothic painting.

 American Gothic at Art Institute Chicago

Since we were starving, but not really dressed for a nice lunch, we grabbed lunch to go at a local Pret-a-Manger and settled oursleves on a bench alongside Lake Michigan.

Lake Shore Drive Chicago

Of course, the first thing I noticed was all the runners zipping by on the path that runs alongside the lake. Ahhhh, how I wish I had easy access to such a beautiful running path … one where I don’t have to dodge cars on winding county roads and hop over cracked sidewalks. I intentionally decided to take the weekend off from running (including missing my scheduled long run), since I only had 36 hours with my friends. But next time I am definitely going to check out those running paths myself.

I also could not get over how massive Lake Michigan was. Literally, you cannot see the opposite shore; it’s just like the ocean!

After walking around a bit more, we headed back to the hotel to begin getting ready for our Saturday night adventures. First stop? Publican in Fulton Market, for a birthday dinner celebration.

But beforehand, I couldn’t resist posing in front of the restaurant’s affiliated butchers shop … you know, being a vegetarian and all.

Publican Chicago

The inside of Publican is very cool (love the lights) and it’s all communal seating.

Publican ChicagoWhile the menu is definitely not the most veggie-friendly, they were terrific about putting together a vegetarian plate full of different sides (and the cheese platter, which is on the dessert menu but we ordered as an appetizer, was delicious). My friends raved about literally everything they had, from the oysters to the various meat dishes, which are all served tapas-style.  Again, I’d definitely recommend Publican (especially to my non-vegetarian friends).

Once our bellies were full, we walked a few blocks to our next stop, The Aviary. It’s so much more than a bar … maybe calling it a “cocktail experience” would be more accurate? We had reservations (if you’re planning to go, especially on the weekend, reservations are a must), and were seated with a round of complimentary shots. Oh boy!


The cocktail menu was a little, hmmm, pricey, but included the most unusual drinks I’ve ever seen (they’re more mixologists than bartenders). I eventually settled on The Ford Model Tee, which came served in a porcelain tea cup (!) and was complemented by a tea pot of steaming dry ice that wafted a tea-scent over the top of the mug. It was surprisingly at first that the drink was cold, but it was incredible: strong but floral, and it definitely packed a punch.

Aviary in Chicago

After a round of birthday champagne, we moved on downstairs to “The Office.” At first, I wasn’t quite sure what that meant (a friend has connections there and made the reservations for us), but we were escorted down to a nondescript door, which turned out to be … an invitation-only speakeasy!

It was tiny, maybe accommodating 15-20 people. We had our own little alcove, including a comfy leather couch; it was kind of like having drinks in someone’s very cool study or living room. The coolest part is that there are no actual cocktails on the menu; it’s all concepts, so you talk through your likes and dislikes with the bartender, who creates a drink just for you.

Aviary in Chicago

We eventually made our way back to the hotel and got about five hours of sleep before we woke up craving greasy food and coffee. Sadly, after breakfast, it was time for T and I to say our goodbyes to S, since we were on the same flight back to Boston, so we jumped in the cab and headed back to O’Hare. And a few hours later, I was walking in my house to lots of hugs and kisses from the kiddos.

It was a whirlwind weekend but I’m so glad we were able to make this work (a big shout-out to S’s husband for orchestrating the trip for her birthday). Once you have kids, you realize just how rare it is to have pure, unadulterated, uninterrupted friend time for more than a few hours. To have nearly two days of it was such a wonderful and special treat.

Have you been to Chicago? What’s your favorite part?