A Week in Chicago

I love Chicago. If I thought I could handle the winters they face there, I would seriously be tempted to trek up north. However since there is a reason I live in the South, I will settle for visiting as often as possible.

It’s not very often I get to have companions on my trips, but when I do the company is wonderful. One of my best friends, Kassi, and I were catching up over dinner in February when I mentioned an upcoming trip to Chicago in April. We talked about how much fun it would be if she could join me and before we knew it, she bought herself a ticket that night.

Kassi is from Chicago so I was even more excited to go with her and have her show me around not as a tourist. This was my 9th time to Chicago in the past 4 years (it doesn’t seem like that many!) so I’ve seen quite a bit, but I was still so excited to visit this time with one of my best friends.

With Kassi joining me for a work trip, it meant my original plan of 4 days was extending to 7 days instead. Granted, the first 4 I spent a lot of time working my event, but that’s still a long time to be living out of a suitcase at once. And I will admit I’m the worst at combining work and vacation trips because I pack everything. My suitcase was just one pound under the airline limit for overweight.

Despite the fact that I’ve been to Chicago a bunch of times over the last couple of years, I’ve still never had Chicago style deep dish pizza. Kassi was determined to change that, so naturally after I arrived on Sunday, the dinner spot was to Lou Malnati’s for a slice of pie.

Y’all – I can’t even describe how delicious and wonderful it was.

Just look at all of that cheese. And the bottom was still so crispy. My eyes may have been bigger than my stomach because I definitely went in for a second slice. It was completely worth killing myself in the gym the next day.

Tuesday was another fun day where we hit up a local bar called Bub City for some live band karaoke. I am no singer but I will always be someone’s back up singer and sing along with them! It was such a fun time and is a great whiskey bar.

Thursday Kassi and I stopped by Cindy’s Rooftop on top of the Chicago Athletic Center for some pre-dinner cocktails. It’s one of Chicago’s trendiest bars right now and has an incredible view of Millennium Park, so it was a no brainer for us to check it out.

Even though it was overcast and cold, the view was still something else. I definitely recommend it for dinner and drinks! You would eat dinner inside but the huge windows and skylights make you feel like you’re out doors without the cold.

Friday we decided to play tourists and hit some of our favorite spots. It was still chilly that day so we ended up not doing as much as we thought, but we made sure to hit The Bean and took one of the Wendella Boat tours.

Because, did you really even go to Chicago without a picture at the Bean?


Kassi is a huge Cubs fan and I’ve never been to Wrigley (I know, for someone who visits Chicago so much there was a lot I’ve never done!) so it seemed like destiny that we visited during Opening Week. Saturday we headed down to the stadium to see the Cubs take on the Pittsburgh Pirates.


We were able to meet up with our girlfriend who works for the Cubs and she used some of her employee perks to get us some killer seats for the game.

Although the Cubs lost, we tried to not let that dampen our spirits. We headed to the field after the game for a quick picture then decided to grab a few beers in Wrigleyville.

Thankfully Kassi had some extra Cubs gear for me to wear to the game so I could fit in! We ended the night with a low key dinner and headed back to the hotel by 11pm.

On Sunday we had a few hours to kill before our flight home, so we decided to venture off for a late brunch at another trendy spot, The Hampton Social. The food was delicious and the rosé of the day was a great way for us to spend a few hours. Plus, how could you not love this sign on their wall?

After 7 days, both of us were exhausted and ready to head home. After over indulging on food and drinks for a week, returning to a routing this week is going to be welcomed with open arms. It was an amazing trip though and I am already counting down to when I’ll be back in Chicago!

What’s your favorite thing to do while visiting Chi-town? Let me know below!


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