Cheers to a much needed mini vacay with Pammie and Donna! The last time we vacationed together was three years ago in Kauai, so this trip was long overdue!

On Friday night, we missed our Nobu rooftop res because it took us 45 minutes to be driven 2 miles. Downtown Chicago traffic is no joke, especially during Lollapalooza weekend.

We ended up at Booze Box, a secret bar in the basement of a sushi restaurant. Right when we walked in, this japanese lady pulled open a side gate and led us down some sketchy ass stairwell into the coolest little dive bar ever. The music, drinks and late night maki def hit the spot.

I couldn’t go to Chicago without going on a river boat tour à la My Best Friend’s Wedding (that scene gets me every. damn. time.). While there was no slow dancing or tearful realizations, I honestly was so impressed by the beautiful architecture. The only other time I visited Chicago was over a decade ago for a weekend in the dead of winter. All I remember was that it was St. Paddy’s Day and they dyed the river green. It was too cold to really do anything back then. Even though it rained the day before I arrived this time, the weather was absolute perfection.

Coffee and vodka? Yes, please (@ Starbucks Reserve Roastery)

Later that day…

Donna: Why is my heart racing???
Me: Maybe it was that flight of espresso martinis you downed? ¯\_(ツ)_/¯

I’m that friend who only orders california rolls at sushi restaurants.

While Pammie and Donna enjoyed the (mostly raw) tasting menu at Nobu, I feasted on this glorious 28-day dry-aged prime ribeye.

If my A5 wagyu isn’t prepared this dramatically, I don’t want it.

The best thing I ate at Nobu (and possibly my entire life) was this whisky cappuccino dessert. Holy shit, you guys. Once that whisky foam hit my lips, I left my body, floated up to heaven, saw my grandparents, came back down, and finished off the remaining layers of espresso gelato, toasted cinnamon crunch and cardamom cream. Their recipe is posted online, but why go through all that trouble when you could just take me to the Nobu in Malibu??? 😏

Since we all binge-watched The Bear, we wanted to try an authentic italian beef sandwich. One of our uber drivers, Kendrick, told us that the best one was at Clark Street Dog. We could kill two birds with one stone and get a chicago dog there, too. He warned us not to ask for ketchup, as if he knew about that one time I asked for it at a steakhouse and was shamed by my entire table. As he drove us around, he also pointed out where people had been recently shot and what areas to avoid walking at night unless we wanted to get popped! So full of useful information, this guy…

We ordered our food and headed over to the attached bar for picklebacks, mules, and quite possibly the worst thing I’ve ever put in my mouth – Jeppson’s Malört. According to our bartender, Evan, it’s a Chicago tradition for out-of-towners to take a shot of what can be accurately described as “rotten grapefruit with the lingering after taste of a tire fire” (among other things). He also suggested we hit up the nearby L&L Tavern where Jeffrey Dahmer and John Wayne Gacy used to troll for victims. Who doesn’t love a good murder bar??? I’ll have to come back when I’m not stuffed with italian beef.

We woke up at the butt crack of dawn to stand in line for an hour before this restaurant opened (sorry for anything I said before I got some cold brew in me 😅). Kasama is the only michelin-starred filipino restaurant in the world, and respect had to be paid.

This trip couldn’t have come at a better time. I got to celebrate an unexpected promotion at work and have a little fun before conference season starts up this week and I’m blacked out for the next couple of months. Excuse me while I cry into my empty Garrett Popcorn tin…