Several high school friends and I agreed to meet up late summer in Chicago. We (mostly me?) needed something to look forward to and a Labor Day weekend trip was born. I had briefly been to Chicago in my twenties and looking back on it, all I remember is a foggy vision of a group dinner at a restaurant where we seemed to be as overdressed as our pizza. What’s that about? I do remember it being a good time, though.

My travel companions this time around, Natalie, Jenn, and Rebecca were more familiar with the Windy City, traveling from their home bases on the East Coast for events such as Jenn attending Lollapalooza—jelly! Natalie feels so connected to Midwest culture (except cheese curds), that she’s daydreaming of relocating. It didn’t hurt that we stayed in a posh neighborhood, The Gold Coast, just blocks from Lake Michigan. The area was quiet and clean and our hotel, The Talbot, had smart tile choices in the lobby and our bathroom. Emerald green subway tile hung vertically in the shower, yes please! That’s a refrain for most places we went, excellent tile-work. Even the brass door hardware was noteworthy. These are the artistic flourishes I miss living in a small Oregon town.

My friends have known me since the mid-nineties when I wore ruffle socks with my school uniform, as an allusion (if subtle) to riot grrrls. And still, these ladies welcomed me into their lives. They’ve got style for days, and on the trip, they all agreed on a common accessory: Labubus. They hung these toothy monsters from their purses, belt loops, and boat bags. And by day 2, they were letting me hang one from my purse too.

Don't Knock the Labubu

One of our first destinations was the Popmart store on Michigan Avenue, home of the Labubus, so my buds could ogle over the display cases of Labubus. The monsters are not available at the store; you’ve got to go on TikTok or What’sApp or step into a dark alleyway to obtain them. At first I was skeptical of the Labubu: their earworm song; a QVC-style shopping channel; their scarcity and batch-launch marketing scheme.

But when I look back at the objects that have comforted me this year: full moon infusions; a sack of shells; rose quartz in my palm; I realize the Labubus could be serving my friends on another plane. It’s not out of the realm of possibility. And if these plush monsters can be stuck baring their teeth, while bearing names like Serenity, then who I am to calculate their value?

A Bath in Lake Michigan

We spent the largest chunk of the trip on a boat charter on Lake Michigan. Beforehand, I was tepid about the idea, thinking we wouldn’t get the docent’s version of the architectural tour (nerd alert), or that we’d miss out on too much wandering time. Then Natalie mentioned she was bringing a tortellini shaped float. And I gave way to the potential fun that presented.

The boat did not yield the docent version of the architectural boat tour, but you know what, I was content to hear updates from my friends instead. It was our first day together and Simonne joined us. She’s also a high school friend, currently living in Indiana. Simonne told stories of globetrotting as a digital nomad, from Morocco to Versaille and how she’s set her sights on a new apartment in Mexico City. And then I promptly imagined a group trip to visit Simonne’s new city.

After the river tour, we went to a swimming inlet with calmer waters than the open lake. Natalie was the only one planning to go in, but once the boat stopped and Natalie inflated her tortellini, I followed the urge to jump in the water too. Instant hilarity ensued and squeals of laughter. Was it the cold? Was it the euphoria of a ritualistic bath? Yes to all of it. Jenn and Rebecca soon joined in, with our assurances that the water wasn’t cold — it was warmer than the Deschutes River— and they floated and splashed until the captain told us it was time to call it a day.

Afterwards we napped like toddlers, all four of us, sharing a hotel room. Who does this? Women who want to relax, enjoy each other’s company, and feel a sense of safety.

Chicago Summer Trip Highlights

Here’s a list of more highlights from my trip that may inform your own:

• Dinner at Girl and The Goat. This was the best of the trip, and you cannot go wrong with any dish, but I suppose you could order too much, like we did

• Museum of Contemporary Art Chicago: I’m going to keep it real and tell you the gift store delighted more than the art. I felt guilty about that until a minute ago when I saw the quote on their website from Condé Nast, “One of the best gift shops (ever).” Jenn, Natalie and I all bought gifts. Fine, I bought myself cutting boards too.

• Chicago Jazz Festival: We popped into this free, lakeside event and it gave me a glimpse into residential life in the city. If I lived there, that’s where me and my kiddo would be all weekend. The grand stage and grassy knoll, the casual confidence of the saxophonist. Take me back to Chicago. I still think about the sweatshirt I did not buy there.

• Walks along Lake Michigan: We used the underpasses to dodge car traffic and access the paved trail along the lake.Then we dodged bikes and running groups. We went to the beach, we went to NorthWesten, we went through the Magnificent mile and past the war protesters. 

• Second City: We went for the jokes and left heartened. I had to give my cheeks massages from laughing and smiling so much. We debated which improv cast member we'd see on SNL next on the walk back to the Gold Coast. 

We went to Chicago and we went together

This trip came in a particularly difficult season for me, and yet Labor Day weekend in Chicago stands out as a little light on the bow of tomorrow. We didn’t party hard. We didn’t chase men. We went on long walks, carried Labubus, ate good food, shared with each other and slept well. I couldn’t have asked for a better time.