As per usual, I didn’t do a great job of getting pictures of the food we ate but I did snap a few.

Mojo Cafe

For breakfast one morning we ate, of all places, in the lobby of the AMA building. Prices were reasonable and the food and drinks were actually pretty great.

Here’s a link to the Majo Coffee website.

The Girl and the Goat

For our “special dinner”, we ate at The Girl and the Goat, a trendy tapas-style eatery that’s not shy about unusual food pairings and snarky t-shirts. It’s not cheap, but if you’re an adventurous eater it’s worth a visit. I don’t think they actually served anything in a mason jar but it’s the type of place that totally would. You’ll likely have to make a reservation.

Again, I didn’t snap every dish we shared but pictured here is their brioche bread (served with relish and pub cheese, because of course), a ceviche-like dish with plantain chips, and some chicken skewers served on cashew butter with what I can only assume is the full and final reserves of oil left in the tri-state-area. The best dish by far, which we did not get a picture of because they got eaten too quickly, were the goat empanadas.

This meal was courtesy of my parents – thanks mom and dad ❤️

Starbucks Reserve (Magnificent Mile)

I wouldn’t normally mention a Starbucks, but this place is next-level. In fact, it’s actually 5 levels with each floor catering to a different type of experience. The top floor, which was closed while we were there 😥, is a rooftop garden overlooking the Magnificent Mile, a stretch of shops and restaurants that runs through the city. The first floor was a relatively typical Starbucks (not in setting but in terms of offering). Other floors focused on special brewing techniques, food and bakery items, and the 4th floor had a full bar that made espresso martini flights. Whether you’re a coffee drinker or not, this location is absolutely worth a stop.

More info on the Chicago Roastery here, including a shot of the building from the outside, which really sells how grand this location is. It kind of feels like what would happen in Apple owned Starbucks.

Portillo’s (for the legendary cake shake)

Though not just in Chicago, I first learned of Portillo’s Chicago location through one of my favorite comedians, Gabriel Iglesias. I can’t explain their cake shake any better than he can, so I’ll let him do it. And surprisingly, this shake cost far less than we both expected it would – and that’s not just the Southern CA effect.

Lou Malnati’s

While perhaps not what I’d think of as the most “authentic” Chicago deep dish, Lou Malnati’s pizza was delicious. It came highly recommended by our friend Tony who knows what he’s talking about when it comes to food. We got this our last night in Chicago… after a lot of walking. Which is to say, please don’t judge us… we got it to go and ate it in bed.

Perhaps worse still… this is not the first time we’ve eaten pizza in bed. 🤷‍♂️

Wilde Bar & Restaurant

I also neglected to get photos of our food at Wilde, but the real memory here anyway was getting to meet up with my old Armor Games friend and colleague, Elza, who is moving to Rwanda soon. It was serendipitous that we ended up in Chicago just a few weeks before she took off for Africa.

Cindy’s Rooftop Bar

On our last evening we stopped by the Chicago Athletic club which has a really neat rooftop bar called Cindy’s overlooking Bean Park… that’s not the name of the park, but that’s how I think of it. Deal with it.

Here’s a picture of Sarah enjoying the view and an aperol spritz. The weather was lovely.

Categories: Chicago 2026