If you were asked to do a roundup of all the fun places to go in Chicago, you’d come up with a pretty exhaustive list. It may take a lifetime to tick off all the boxes, in fact. Anyone feel like doing a ‘Groundhog Day’ scenario in the Windy City? Take a number, folks. But since nobody lives forever, here are a few solid choices to get you started.
This former hipster enclave on Chicago's near west side is going decidedly mainstream, but it’s not all bad! You’ve got solid restaurants, art galleries and a very chill vibe at your disposal when you explore this part of Chicago. Winter visits can include a spin on the neighborhood’s outdoor ice rink. Browse original pieces of art and jewelry for sale at the neighborhood’s iconic Flat Iron building, then finish things off at one of the many packed watering holes along Division Street.
This neighborhood has long been associated with Chicago’s working class Latino community, but things are looking a bit more hip in Logan Square these days. And while that creeping gentrification might be a tad regrettable, at least the hipsters had the good sense to keep the Mexican food. The annual beer-infused carnival sponsored by New Belgium Brewing Company, Tour de Fat, happens right at the heart of Logan Square each summer. This freewheeling festival combines art, bicycles and (you guessed it) beer in a display of weirdness that’s distinctly Chicago.
This bustling district is the seat of most of the packed office buildings and skyscrapers in Chicago, and many people might hang on to the notion that it empties out after dark. But with the addition of Millennium Park to showcase stunning landscape design and host open air concerts in a Frank Gehry-designed band shell. And with the infusion of fun, original entertainment venues such as AceBounce, the Loop is becoming a place to linger long into the night. The Chicago Loop Alliance sponsors regular hangouts in alleyways and side streets that showcase local artists, musicians and offer Loop-ers a chance to mingle, sip beverages and appreciate a side of Chicago that many locals didn’t even think twice about in the past.