I spent 48 hours in Chicago for the first time and left with 4 regrets

I decided to book a different hotel each night of my trip so I could get a taste of the Chicago travel scene.

I spent my first night at theWit Chicago, a downtown Hilton hotel with a whimsical take on modern luxury. I booked a Spa King Guestroom for one night for $240. It was a corner room on the 16th floor with floor-to-ceiling windows on every exterior wall. Asymmetrical mirrors, cartoonish light fixtures, and mismatched nightstands made my stay feel unique.

While taking a bath in the large soaking tub with a view of downtown Chicago, I felt more wrapped in luxury than I have in some $1,000-a-night hotel rooms, so I was bummed I only booked one night.