Chicago Guide: When Your Best Friend Visits Your City

Chicago Guide

Your best friend of all time is visiting you in Chicago and you only have one weekend to be the best tour guide and show her your city. What do you do? Where do you go? The options are endless right?

In one weekend it is totally possible to show your best friend each side of Chicago: classic Chicago, glam Chicago, and even gritty Chicago. So how do you pack it all in?! Don’t fret- you got this.

My best friend Ella of Mod Med Blog was in Chicago for two weeks doing her medical school interviews before her residency, and the last time she was here was 3 years ago for New Years Eve (SO FUN but SO COLD). So I had to show her my favorite parts of Chicago and take her on an adventure, naturally.Chicago Guide


Starting off the weekend right, I took Ella as my guest to the American Cancer Society’s Skyline Soiree. Ella and I went to support an amazing cause at a lovely venue. She got to see Chicago in full swing at bustling event. After, we ended the night at Esquire Champagne Room in Gold Coast. This is what I mean when I say classy Chicago. We had a delicious bottle of sparkling wine with a few yummy apps. Live piano playing in the background with the touch of pink velvet. Yes Yes Yes.


Rise and shine! Ella and I started off the morning with a glutes camp class with the amazing personal trainer Jeremy at Trump hotel. After we sweat out all the champagne, we had a lovely brunch at Terrace 16 with consisted of fresh made bread, crab roll, salad and sweets. All the while we sat overlooking what I think is one of the best views in Chicago. I have to say- every. single. time. I stop by and see my friends at the hotel, everyone is so welcoming and they strive to ensure your experience is exceptional. Terrace 16 was exactly that.

Afterwards, we walked along the river walk and then got ready for a GIRLS NIGHT OUT. We started off the night at Bounce Chicago on the rooftop, and ended the night at LIQR Box. If you haven’t been to either, you must check these bars out! I love the views at Bounce and I didn’t have a drink (aka juice box) from LIQR Box that I didn’t like! Win win.


Sunday was as Chicago as Chicago can be. Thanks to American Airlines, we were able to catch the Cubs game in style in the 1914 Club. The weather was perfect and the energy was through the roof fun! I am only going to a Cubs game 1914 American Air Club style for sure. Afterwards, we headed over to Chicago Helicopter Experience for a sunset helicopter ride (!!!!!!). I have flown with CHE before but this time was absolutely magical. The sunset was stunning and Ella and I had so much fun from the second we got to the terminal we played games, had champagne, and toasted to a fun flight. Check out my video of our experience HERE.

A few of my other favorites go to-s when your bestie visits your city:


Ella Elli Chicago: Brunch anyone? The decor and food go hand in hand at this Lakeview restaurant! I recommend the french toast and side of potatoes… and their mimosa service 😉

3 Arts Club Cafe: Ella and I went here before and it is one of my top 5 restaurant recommendations when someone is visiting Chicago. The ambiance, chandeliers, fountain, food, Bellinis… need I say more?


The BEAN! A Chicago classic for sure but you must get the perfect shot in front of the bean.

Architecture Tour: Grab yourself some rose and hop aboard the Chicago Architecture boat tour. It is about 90 minutes and so fun to cruise down the river.

Ride bikes along the lakefront: Something so simple but SO fun and its exercising + great views all at the same time.

Ella and I’s adventures went by too fast, but I can’t wait for her to come back and hopefully get her residency here (no pressure Ella 😉 ). What do you love to do with your BFF when they are in Chicago? Holla at ya gurllll and let me know in a comment below!



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