Krupa KumarComment

How to experience and eat your way through Chicago in two and half days

Krupa KumarComment
How to experience and eat your way through Chicago in two and half days

Up until last year, I never thought I would plan a trip to the mid-west. Chicago was on my list of places but I didn't think we were going to explore it anytime soon. That changed when one of my closest friends asked me if I would be her bridesmaid and of course, I said yes and we took a trip to Indiana and Illinois in May.

The trip felt like a true adventure. As we made our way through our first American wedding, piles of food, and celebrating our wedding anniversary we did our best to take in the unique, history of the Chicago. Here's are my recommendations for Chicago


  • Much like San Francisco, the weather keeps changing so be sure to layer up. Everyone is dressed well and style seems laid back.

Chicago dress

Things to do

  • Explore the Navy Pier. Cotton candy, carnival rides and a fun atmosphere. Highly recommended the Ferris wheel at night, it is romantic and cozy all at once!

  • Go on the architecture cruise to learn about the history and see Chicago's truly unique skyline

  • Walk the magnificent mile & stroll through the river walk to relax and decompress. Soak in the weather and views.

  • Visit The Art Institute of Chicago, they have a variety of exhibits. (love their gift shop)

  • Enjoy a day at the Shedd aquarium. We spent more time here than we anticipated.

  • Go for a morning run in the Millennium park and check out the Cloud Gate statue. Highly recommend checking out Grant park too.

  • Check out the sky ledge at the Willis Tower.


Places to Eat


Places to stay

Pro tip

  • Buy the Chicago city pass or other passes that get you admission into a variety of attractions.