A Chicago Weekend

I’ve mentioned a few times that I visited Chicago over Labor Day weekend for a wedding. I knew I was going to have a blast in the Windy City and was pretty excited to hang out with friends from college who I haven’t seen in years. And to see one of the most beautiful weddings of all time. Where I cried several times so fingers crossed that’s not captured in photos for all eternity. My friends and I arrived in Chicago on Friday afternoon and had about 48 hours until we had to get wedding-ready so we decided to hit the town. And hit the town we did.

First stop: Get a slice of Chicago deep-dish pizza. Priorities, people.

I asked for deep dish recommendations and we set off in search of Lou Malnati’s. Unfortunately, there was about a 2 hour wait and we were already well on our way to hanger system so we scrambled for a Plan B. Geno’s was also on the list and nearby and (score!) we were able to get a table right away. An appetizer of roasted brussels sprouts and 2 glasses of wine later, our pepperoni and sausage deep dish arrived…and was promptly devoured. It was absolutely delicious and I couldn’t stop after just one slice. Thank you, Geno’s waiter, for recommending the sausage patties instead of crumbled. It was 100% the right call. Stuffed to the gills, we (slowly) walked back to the hotel suite after a quick stop for libations. We were celebrating after all.

On Saturday, we all wanted to explore the city. But first, brunch. To Little Goat Diner! As it turned out, Little Goat Diner happened to be one of the cutest restaurants I’ve ever seen. And home to the Best.Damn.Bloody.Mary.Ever. I’m still dreaming of this Bloody Mary. It was one of those moments where you wanted to keep sipping but knew that each sip meant you were closer to the end.

Little Goat’s menu was extensive and filled to the brim with just about every breakfast dish to satisfy your craving. It would’ve been a tough choice to make but once I locked eyes on the “Big Fat Elvis Waffles,” I was sold. Waffles that would (I’d imagine) rival those of JJ’s Diner, peanut butter butter, maple syrup, sliced bananas and BACON!!! Dear god, it was majestic. Whatever peanut butter butter is, it was pure magic. If you’re in Chicago or visiting Chicago, RUN to Little Goat Diner! Your stomach will thank you.

Stomachs full, we decided to walk to Millennium Park…Well, to be specific, we walked to Cindy’s Rooftop Bar overlooking the Park and Lake Michigan. Cindy’s specializes in craft cocktails and U.S. News recently named it a Top 10 Rooftop Bar in the U.S.! It definitely earned its spot with strong cocktails with names as creative as their ingredient lists. Watching the bartenders work was mesmerizing and it took awhile to choose a drink. I went with the “Howl at the Jun,” a take on the classic French 75. I needed both hands to hold this drink, no exaggeration.

Later that day, I went on a little solo stroll to just walk around the city and take it all in. I also stepped into Goddess and the Baker for an iced matcha latte to help balance out the pizza, Bloody Mary, waffles and cocktail. Their “Eat Now Caffeinate” sign drew this blogger like a moth to a flame (No shame). Once I rejoined my college friends, we went back out on the town to a karaoke bar and even found a late night arcade. Sunday morning flew by in the blink of an eye and before I knew it, we were heading to the Adler Planetarium for a wedding.

Chicago was an incredible time and I am so happy I could be there for my friend’s big day! I loved catching up with friends and dancing the night away. Chicago, I’m definitely coming back for a Round 2.

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