I didn’t expect to love you this much Chicago, but you definitely won me over. A beautiful city filled with culture, fast-paced lifestyle and really good food. My favorite type of cities are ones that have a certain hustle to it, yet have dedicated public spaces with beautiful architecture.

ITINERARY

  • November 2016 - 2 days @ Loyola Chicago

  • November 2016 - 3 days @ Airbnb in DT Chicago (ANOTHER GREAT AIRBNB. It was this huge loft that fit all 10 of my pbros. So cozy on a Thanksgiving night!)

  • May 2017 - 3 days at ALoft City Center

  • September 2018 - 3 days at ALoft City Center

  • March 2020 - Celebrating all time #fav Chris Wang’s 27th birthday!

HIGHLIGHTS

  • Walking through Millennium Park on a cold brisk morning and seeing all the cool public art. Go for the Bean and Crown Fountain!

  • Catching views at Willis Tower. If the wait isn’t that bad it is definitely worth the view and photo op. I out’d out of it the first time and really regret it because John Hancock Center view does not compare to Willis Towers’. I’d say it’s only worth if the line is short and you can get up within 30 minutes. Otherwise, ya– skip it.

  • Doing the architecture tour! It was freezing in November, but way better when I went back and did it in March and September. Chicago has some beautiful architecture because they rebuilt they city after a fire in 1871.

  • Spending a cold winter day inside the Art Institute of Chicago.

  • Eating at Blackbird --  a Michelin Star restuarant and three course meal for $25.

  • Loving the unique flavors of Jeni’s Splendid Ice Cream -- I got a mix of riseling poached bear and goat cheese with red cherries. 

  • Sharing tapas at Girl and the Goat. Easily one of my favorite restaurants in the US to date! Girl and the Girl has a few sister restaurants including Little Goat Dinner and Duck Duck Goat which I have yet to try yet!

  • Brunching (and instagramming) at The Hampton Social. 

  • Visiting Northwestern Kellogg and UChicago Booth. MBA tours are such a great way to visit a school, get to know the culture, and have the ability to really picture yourself there.

  • Fun nights out in Chicago. One of my favorite bars I went to was Slippery Slope felt like such a cozy dive bar with all the Christmas lights strung up! Mother, Tao, Bounce, Prysm are also other fun / chill bars to check out.

  • Head to Cindy’s after Millenium Park for amazing views. Bomb views, and so hip that we ran into girls from the Bachelor there! (Jasmine Nguyen was SO nice.)

  • Drink omakase at the Aviary. Totally worth the hype, recommend doing your research before hand because some drinks are hella cool. My favorites— Branding Iron (off the drink menu for cool wooden coaster), Circle Drink, Westward Expansion, Time After Time, In the Rocks. Also, the truffle popcorn and chicaroon here is bomb.

  • Happy hours galore! One of my favorite things about exploring a new city is trying out different happy hours. (If I'm not working, I wanna be drinking LOL) Ema was such a great find. Amazing Mediterranean tapas (my fav type of meal hehe), $5 eggplant spread, $5 beers / wines, $5 hot / cold tapas. 

  • Playing Whirlyball, bowling, and lasertag. Fun for a team offsite!

  • Spending some amazing quality time with friends and coworkers.

    • Seeing one of my first friends in college, Caressa killing it in grad school.

    • Planning a trip where my fraternity pbros (Insun, Christina, Candice, Liang, Stephen, Adam, Mich) who flew up to reunite from all over the country. 

    • Getting to celebrate good friend Chris Wang’s birthday! Happy to get to spend time with Chris Wang, CBest, Morris, Grace, Jpark, Vishnu, Daniel Li in a bomb city!

    • Cooking an early Thanksgiving dinner with some of my great friends from college. 

 

LOWLIGHTS

  • Freezing on the architecture boat tour in November. Not the best idea in 48°F.

  • Being forced fed overhyped Chicago style pizza. Not sure what all the raves are about…. It’s just breaded lasagna at this point. (But if it is your first time in Chicago it is still definitely worth cehckin gout. If you are looking -- Chicago Pizza and Grinder Oven Company, Giordano Bros., and Lou Malnati's all can give you an authentic experience.)

  • Paying $15 for drinks at the John Hancock center. It is a great view, and I don’t have to wait in line but wasn’t anything spectacular.

  • Overhyped and long longs at Wildberry Pancakes and Cafe. Waited almost two+ hours for this, and honestly did not see the hype.