Despite living for years in the Midwest, it wasn’t until I returned to America’s Heartland that I found time to venture to the capital of the region: Chicago.

My friend Rick and I went all out when we visited the Windy City for a music festival back in July. We bought our tickets and then spent some time figuring out what to do in Chicago. Inundated with options, we decided to just dive right in. We found a nice hotel room at the Fairmont, scribbled out a list of museums to see and were off. 

The concert festival was held in Union Park, which is a beautiful spot located in the heart of the city. That experience, however, is a whole other story. Let me instead focus on the other fun things we did.

La Pasadita

La Pas is arguably the best Mexican food chain in the country, and three of its flagship restaurants sit on the same street block. Walking down Ashland, it was hard to choose which restaurant to enter. Ultimately, we chose the newest location, which was commandeered from an Italian who thought he might open a Tex-Mex spot on the same street. The food is authentic and must be tasted to be believed.

Garfield Park Conservatory

The Garfield Park Conservatory is a quiet and beautiful part of Chicago that often gets lost in the hustle and bustle of the large city. There’s so much to see in the Windy City that trees and foliage seem to hold less interest.

The conservatory is home to thousand of types of plant life, and often hosts plant rescue sales that place needy specimens to good homes. They were recently victimized by a hailstorm in Chicago that destroyed almost half of the glass panels protecting the plants inside. It remains open to the public, and is still beautiful as it ever was. In fact a visit now could mean a great deal to the institution.

Jazz Clubs

Many cities have respected jazz clubs, but none like Chicago where Jazz was born out of one of the most notable periods in American history. As Capone was making millions off of illegal alcohol, Earl Hines and his Grand Terrace Café Orchestra were setting the tastes of the nation broadcasting coast-to-coast live from Chicago. As a result of the Prohibition culture and the Jazz that came after, Chicago has some of the best Jazz bars in the world.

Formerly owned in part by one of Capone’s Henchmen Jack McGurn, the Green Mill Cocktail Lounge has seen its share of slit throats and cut-out tongues. Business roared through the 30's, 40's and 50's with people stopping in after shows at the Uptown, Riviera, or the Aragon Ballroom. In the 80's it was purchased by its current owner and restored to its Prohibition era décor. A must see for any Chicago traveler.