May 21, 2015 – It was my first time in Chicago. I spent just a little over one full day there, but I think I got about a full weekend’s worth of activities done. I actually arrived late night on Wednesday and only had time for a late dinner at Pequod’s Pizza. Then it was bed time, but the next day was filled with lots of. I was able to eat at places where there is usually at least an hour without having to wait at all. The trick? Eat during the off hours. I was also able to catch a show at the Second City called #DateMe: An OKCupid Experiment. It was hilarious and I highly recommend it especially for people in their late 20s and 30s.
Here’s a quick rundown of my itinerary:
Wednesday, May 20: I arrived at around 8:30pm and headed straight to Pequod’s Pizza for some deep dish pizza. Some say it’s the best, and it was definitely good, especially its caramelized crust; however, my favorite deep dish is still Little Star Pizza in San Francisco.
Thursday, May 21: Aside from non-stop eating, I was also able to walk the Magnificent Mile, making a visit to Millenium Park and the famous Cloud Gate, and also passing by other sites such as the Art Institute of Chicago and the Willis Tower (aka Sears Tower). But more importantly, here’s what I ate:
Stan’s Donuts – Very bright and clean shop with very pretty donuts. I went for their pistachio lemon old fashioned donut. It was tasty, but too sweet for my liking.
Do-rite Donuts – Unlike Stan’s Do-rite was more of a dive, but still very clean and welcoming. Just so I could easily compare, I went for their pistachio Meyer lemon glazed donut. The donut was more like a cake donut and the whole thing was not as sweet as Stan’s, which I liked. I will definitely have to return for their bacon donut and their fried chicken donut. JONASAPPROVED!
Hero Coffee Bar – I’m no coffee connoisseur but I thought their coffee was just okay. No pretty latte art or anything, but their coffee got me through the rest of the day, and it was a very long day.
Coco’s Deep Fried Lobster – I’m super Asian, so if there’s two things I like, it’s deep fried and lobster. Even better – no peeling involved. JONASAPPROVED!
Portillo’s Hot Dogs – I had deep dish the night before and I had to check the Chicago dog off my list too, specifically from Portillo’s, the most famous of them all, and the original location on Ontario St. The hot dogs were pretty small, especially since I’m used to Costco size, but there’s a certain freshness that you can taste with their hot dog and bun. Next time, I must try their Italian beef. JONASAPPROVED!
Signature Lounge at the 96th floor of the John Hancock Building – Why pay to go up the 94th floor of the John Hancock Building for a view of Chicago when you can pay for a (slightly overpriced) drink instead and be two floors higher? The lounge looks dingy but it’s the outside that matters. The view is amazing. JONASAPPROVED!
Glazed & Infused – It’s my third donut stop. This one I liked because their donuts were a little fluffier (and a lot bigger). Still, as I type this, my favorite donut is still Twisted Donuts in San Francisco.
The Purple Pig – We arrived during happy hour, but they are so popular they don’t need a happy hour menu. We were fortunate to be seated immediately, and which seemed to be the last open seats. The food was amazing, especially the deep fried pig ears. JONASAPPROVED!
Girl & the Goat – Again, we arrived at an off time, around 10pm, and we were able to secure a walk-in spot in the lounge. A few minutes later, an actual table opened up for us, but we were already comfortable at the lounge and the full menu was available there anyway so we stayed. This was the perfect end to a one day trip, or any day trip. Everything was great. My favorite was probably their roasted pig face, and definitely their budino to end the night.