Earlier this year, I went to a work conference in Chicago. I had a GREAT time. I was a little anxious, but I ended up hanging out with a coworker the entire trip and we ended up being a perfect travel match. I’m sharing what we did – food, drinks, and exploring the city a little. I’d recommend every place we went!

Food + Drink

Starbucks

Chicago is home to the largest Starbucks in the world. It has 5 floors, with a different theme on each floor (I have a photo shown below that lists the floor details). I loved that it had a bar with coffee themed cocktails (I tried the Cold Brew Spiced Rum and it was fantastic) and a rooftop, perfect for sipping said cocktails with a view!

Kyuramen

It ended up being a little chilly while we were in Chicago, which was perfect for me. I’d definitely rather be too cold than too hot, and Ramen sounded like the perfect way to warm up. I’m still having dreams about the chicken ramen and Passion Fruit tea I had there! The restaurant was also really nice, with little nooks and booths for the seating.

Cerise Rooftop Bar

We just happened to find Cerise Rooftop Bar while we were on Google Maps looking for something near where we already were. Man, what a find! The cocktails were delicious (a bit pricey, but honestly that’s pretty average for Chicago), and the VIEW! The view was incredible, with the Sears (Willis) Tower in the back. The rooftop itself is 26 stories up, and I LOVED it. A pretty cocktail with a pretty view is my dream bar scenario, so this would definitely be on my list to check out for anyone who visits.

Portillo’s

I’ve been to Chicago quite a few times, but I’d never been to Portillo’s until this trip. It was one of the spots I wanted to be sure to hit, so we had dinner there one night. I love a good Italian Beef Sandwich, and theirs did not disappoint. The decor was really interesting too. I was looking around, discovering little things they’d put in the whole time we were eating.

The Redhead Piano Bar

While walking back from Portillo’s, we decided to stop into this little bar we passed while walking there from the train earlier in the night (that was a lot of our trip, honestly, and it ended up being a fun adventure!). The Redhead Piano Bar sounded interesting (especially as a redhead myself), and it was! There was a girl playing piano, very well, people dancing, and great cocktails (I tried the Sonya’s Juicy Peaches, and of course, The Readhead, and both were great). I think we could’ve stayed there quite a bit longer, but we had a long commute back to our hotel and didn’t want to be exhausted for the conference the next day.

Fogo de Chao

I spent most of the week with just my coworker, but our boss also wanted to take us to dinner one night. We decided to try a place near our hotel, Fogo de Chao. It’s a Brazilian steakhouse that was within walking distance. The food was great (the lamb was fantastic, and there was a lemon chicken I’m still drooling over), but the service was terrible. I love Brazilian steakhouses, but I don’t think this one is on my list of places to return, just from the service.

King’s

After the steakhouse, my boss headed back to the hotel while my coworker and I explored a little more. We found King’s, a sports bar with a bowling alley. We stopped in for a couple of beers before heading back to the hotel for the night.

Hot Woks Cool Sushi

We debated between Thai and Indian food, and Thai ultimately won. We picked a place close to our previous location, and decided to check out Hot Woks Cool Sushi (Michigan Ave location). It was pretty good! I had the mango chicken and a mango cocktail with some crab rangoon.

Views

Chicago has so many beautiful views. I love a big city skyline, and this was definitely the place for that!

Things to Do

The Medieval Torture Museum

I found this museum while looking at Google with my boss. It sounded right up my alley, and was the one thing I definitely wanted to do. My coworker was completely on board with it, and I think we both really enjoyed it! I’ll save the more gorey photos for a separate post, but it was a fun little museum if that’s your thing!

Conference Outfits

We DID go for a conference, so I got to dress up a little. I love fun work outfits. You can check all of my Chicago outfits here and more of my work outfits out here.