Wow, I love Chicago. Lindsey and I headed to the Windy City with two of our friends, Marissa and Meg back in July for a short but jam-packed trip and truly fell in love with the city. We’re already planning a trip back, but in the mean time, here’s the rundown of how we spent our all-too-brief time in Chicago.


The four of us arrived on three different flights, two of which were pretty delayed. As a self-proclaimed master planner, I was pretty excited when our original flights had us all landing within 5 minutes of each other in the same terminal, however that plan quickly disintegrated. It turned out that Meg and Lindsey’s flights were delayed but still arrived within 20 min of each other, so they met Marissa and me at the hotel. We all changed and headed over to Wrigleyville for a Cubs game.

We all loved Wrigleyville, the neighborhood was so cute, the bars were fun and the baseball game was great. I couldn’t get over how charming the stadium was with all of the ivy wrapping the structure.

After the game and post-game Wrigleyville adventures, we went searching for deep dish pizza. We really overindulged that night. We were waiting for our table at Lou Malnatti’s and were starving, so during our 90 minute wait, we went next door and got some drinks and nachos at a Southern themed bar. We were all so pleasantly surprised at the prices, we shared an $8 sangria fishbowl alongside our delicious cocktails. After our apps, we went back for our deep dish. Personally, I thought I was going to explode with every bite, so I barely finished my slice, but loved my first bites of deep dish. So much, that I ordered some pies on Amazon once we got back to NYC.


We got up and ready pretty early with hopes of beating the crowds at Cindy’s for brunch. We got there and were greeted with a 4 hours wait. Without plans to actually wait it out, we decided to at least stay for a drink on the balcony overlooking the lake, so we were pleasantly surprised when we were about to leave and the hostess said we were next on the list. The food was trendy and good, but the location is really the star. Afterwards, we went to The Bean across the street with the masses.

Hung out there for a few minutes and then headed over to Hampton Social for a quick snack and drink before our tickets for the Architecture Boat Tour. This tour is something on everyone’s list of must see’s but it truly was a great experience. I even say that as someone who is prone to seasickness. Our docent was so knowledgeable, the scenery is beautiful and we really lucked out with perfect weather.

Afterwards, we did a bit of the river walk and grabbed some coffee before heading back to our hotel to change for dinner. We ended up eating at Purple Pig, just around the corner from our hotel. Another great meal. Afterwards, we headed to Three Dots and a Dash for some fun drinks in novelty cups. 


We made some interesting choices when it came to travel, our flights back home were pretty early, so it was a very early wake up call for us. Something that we always struggle with for weekend trips is the balance of the right time to come back on Sundays. Do you go early so you have time to unpack and rest up for Monday or do you say ‘f*ck it’ and come back late night on Sunday? This was our first time picking the early flight. I still haven’t decided which is the better choice…


Our Hotel: Marriott Chicago Downtown Magnificent Mile

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