Five things to do while in the Windy City.

Chicago has a lot of nicknames: the Windy City; the Second City; and the City of Broad Shoulders, just to name three. But whatever you choose to call it, there's no denying it's one of the most dynamic and culturally rich cities in the US. The next time you find yourself with a few free hours in the lakeside metropolis, here are five things we think are worth checking out.


1239 W 18th St, Chicago, IL 60608

The food scene in Chicago has rightfully earned its place as one of the best. At S.K.Y., Chef Stephen Gillanders is creating buzz with his Asian-accented cuisine made with all the precision he learned after a decade working alongside Chef Jean-Georges Vongerichten. The signature fried chicken with fermented hot sauce alone is worth the hype.


1852 W 19th St, Chicago, IL 60608

A third of Chicago's nearly 3 million residents are of Latino ancestry, and most are specifically of Mexican descent. With such a thriving Mexican population, it's logical, then, that the city is also home to one of the nation's best spots to view Mexican art. A strong program of exhibits and guest speakers keep it engaged with its surrounding community and admission is free to all visitors.


427 S Dearborn St, Chicago, IL 60605

Chicago's skate and streetwear culture doesn't usually get the attention it deserves, but Jugrnaut is a one-stop shop for its favorite apparel. Inside the South Loop boutique, customers will find industry giants like Stüssy and Bape mixed in with brands outsiders might be less familiar with, like Cazal and 10 Deep.


3733 N Southport Ave, Chicago, IL 60613

The Music Box Theatre was built in 1929 and, aside from a few brief closures, has remained in constant operation since. Today, its grand architecture is home to a program of independent and foreign films, as well as the occasional showing of classics (cult or otherwise).

Barry Butler Photography


5491 S Shore Dr, Chicago, IL 60615

Chicago's lakefront measures more than 18 miles on the city's eastern border. That's a lot of ground to cover and while there are many beautiful spots, some gems stand out above the others. Jutting out into Lake Michigan, Promontory Point has what a certain subset of locals considers to be the most striking skyline views in town. It's not far from the University of Chicago campus, which is also in the Hyde Park neighborhood and features a central grassy field dotted with bonfire pits available to the public. Take a seat on the stone steps tracing its perimeter to watch the tide come in and out with Chicago's remarkable architecture in the background.