I’m lucky beyond measure to have a great group of high school girlfriends who get together whenever we’re all in our hometown. Instead of waiting for the holidays or the next wedding, this year we decided to do a proper weekend in the city we call home (even if most of us live elsewhere): Chicago.

With just over 48 hours to wine, dine, and catch up on each others’ lives, we hit the ground running.  Here was the outfit I wore to travel and then for dinner at a local Italian restaurant:

Shirt dress: Merona (I previously mis-IDed it as Gap) – thrifted
Sandals: Saltwaters by Hoy – retail
Sunglasses: Ray-Ban – retail

Side view:

Roll those roll-tab sleeves for better ventilation.

It held up surprisingly well given that I wore it to work, sweat in it for an hour waiting for a state trooper in the Atlanta heat following a minor car accident, sat in it for a two-hour flight, and then wore it straight to dinner since my accident meant I took a later flight and had no time to change.

You know what the cure for all that nonsense is? Good friends and a good negroni.  :)

The next morning I was up for a run around my hometown wearing workout clothes I had thrifted on the way to the airport. I had forgotten my usual running stuff at home since it hadn’t dried yet. Thrifting to the rescue!  For under $10 I had perfectly serviceable shorts, a running bra, and a tank top, all of which I left at my parents’ house so I don’t have to pack workout gear next time I go home. Genius.

After meeting up for coffee with two of the ladies, we hopped on the train and headed downtown to meet another friend (two others had joined us for dinner the night previously but couldn’t make the city festivities). We hopped into a ride service to get to her apartment and had the most Chicago-esque conversation possible with the driver. Topic #1: the Cubs’ prospects for beating the Cardinals that day (done!); topic #2: where you can eat the best Chicago-style hot dogs (I don’t eat meat but if I can help it a Portillo’s jumbo cheese dog will be my last meal before I leave this earth); and topic #3: obviously Lou Malnati’s does the best Chicago-style pizza.

Once we met up with our city-dwelling friend, we went for a stroll along the recently completed riverwalk and stopped for pictures with the giant deer…

This is the definition of #random. Source

…before sitting down to rosé and a cheese plate at City Winery. The people-watching was excellent as party boats and kayakers trawled the Chicago River and people meandered alongside it.

Here’s my “day” outfit:

You can tell I’m super happy to be in my favorite city with some of my favorite people. The guy behind me, however, might be picking his nose. Can you spot the Chicago theater sign?

Shirt: Zara – thrifted
Shorts: American Eagle – thrifted
Crossbody bag: Marco Avané – thrifted
Necklace: DIY from thrifted vintage bracelet (closeup below)
Sandals: Saltwaters by Hoy – retail
Sunglasses: Ray-Ban – retail

I tucked the front of this split-hem shirt into my shorts to give the outfit a jaunty little flair and let the back hang out to give some interest and showcase the two-toned gold thing going on. Sorry I didn’t get any side shots! I still feel a little weird asking people to take outfit pics, even though people generally oblige and they always turn out better than what I take myself.

Next up: dinner at Momotaro, a very hip Japanese restaurant. I swapped my shorts for my white Banana Republic trousers to dress up my dinner look a bit; the gold lamé shirt I already had on took care of the rest.

What our table looked like.  Source

We feasted on small plates like tomato tartare with milk bread, mentaiko spaghetti with cod roe and an egg, age dashi tofu (a round tofu cake with watermelon turnip purée, scallions, and flaked tuna), shishito peppers, una kyu (barbecued eel roll), and sashimi and beef fried rice for the half of us who eat meat/raw fish. Black currant mochi and green tea chocolate crunches were dessert.

I unfortunately took no pictures, since the lighting was so dim and we were all too focused on salivating over our meal (that part’s not unfortunate!), but here’s what the internet shows for the tomato tartare:

YUM.  Source

My favorites were the tartare (not actually involving any meat) and the shishito peppers, but everything was delicious, including the cocktails. Thanks abundantly for dinner, Steph (and David)!

Next we headed up to the rooftop bar at London House, the hotel where another friend had snagged us a comp room thanks to how often her husband travels for work.  Many, many thanks Maddie (& Dan)! The view was incredible – and kind of scary? especially after a cocktail or two:

Source

By this point I was feeling extra fancy since my normal vacation digs are friends’ guest rooms and my normal vacation fare = Subway on the road. After much laughter and only one broken glass, we headed back to our room and drifted off to dreamland.

The next morning I was up for a run along the lakefront. Running in a different spot from my normal route is one of my favorite parts of vacation; there’s something truly invigorating about taking your exercise while taking in a new (or newly revisited) view.

With Chicago in particular, I have a lot of memories: visiting downtown often for field trips and theater as a kid, interning one summer on Michigan Avenue, and taking a college course on Chicago architecture in literature. So I still love to get facetime with treasured landmarks like the Art Institute lions, the Field Museum, the bronze Bowman and Spearman, the Congress Hotel, and a distant Sears Tower (I will always call it the Sears tower). I even tipped my hat to the alien monstrosity that has landed on Soldier Field, then turned around to run on the lakeside, ending back at the Wrigley and Chicago Tribune towers by the hotel.

Views from the hotel:

So many architecturally magnificent buildings masquerading at ground level as 7-11s (or in this case, Hard Rock):

When you randomly meet a dinosaur on your run (Field Museum):

Railyard with a great view:

Part of Millenium Park being put to good use:

It’s a fountain; the mouths of the people portrayed spit water. I always wonder who those people are and if they ever get weirded out seeing their gigantic selves as part of a public art installation…

I got several more GREAT shots but my phone is still misbehaving and corrupted most of them. Grumble grumble grumble.

Breakfast and a shower later, I was ready for the train ride back to my parents’ house for lunch and goodbyes to all:

Shirt: Madewell – thrifted
Shorts: Bebe – thrifted
Braided leather belt – unnamed, thrifted
Accessories: same as above

^^That is the best my mane ever looks – right after I went for a run (and didn’t wash my hair). Go figure.

Closeup on the bracelet-turned-necklace:

All this packed in the Samsonite Silhouette I borrowed from my mom, the tan twin to my grandma’s aqua blue bag – you can see it below.

Fistbump to Cori, who wants you to know she thrifted everything in this rad outfit except the shirt (and who is my environmental soulmate; she snagged that empty Starbucks cup beside us for recycling):

Oh hey Wrigley building and Tribune Tower.

Cheers, ladies – here’s to friendship and to next time!