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A local’s guide to Chicago


As one of the most populous cities in America, the Windy City has no shortage of things to do. It’s no secret that this metropolis is home to some great tourist attractions; the Chicago Theater, Wrigley Field, Millenium Park and Cloud Gate all come to mind pretty quickly. To get the best experiences out of your travels, having an insider’s guide to the hidden gems is unbeatable.

A local’s guide to Chicago

Garfield Park Conservatory

The fast-paced lifestyle of Chicago gives any bustling city a run for its money, but don’t let its skyscrapers and crowded streets fool you. There are lush and beautiful naturescapes to be found here, and Garfield Park Conservatory provides this without even having to venture outdoors. A favorite retreat for locals, it is filled with trees and flowers that make you forget about the city just outside. Plan ahead to participate in one of the special events, like beekeeping and composting demos, or tasting fruit grown within the Conservatory’s gardens. And if you can’t take an island vacation, the building’s tropical temperature makes it easier to pretend you’re beachfront. The warm environment is an especially welcome retreat during the bitter cold of Chicago winters.

Hop aboard the 606

Once an abandoned rail line, the 606 is now considered to be a usable work of art through the city. It was transformed into a recreational trail that is now used as alternative transportation. Locals use the 606 to run, walk, and bike, either for leisure or to get around town. It is set above the streets, giving a unique perspective to the city, and connects four neighborhood parks. It is a great spot to find local artwork, usable green space, and special events.

McCormick Bridgehouse Museum

The Michigan Avenue Bridge, which was the first bridge of its kind ever built, can be fully appreciated at the McCormick Bridgehouse Museum. Spanning multiple levels, this museum offers visitors an interesting perspective on the city’s most famous movable bridge. On lift days, you can watch the giant gears responsible for the raising and lowering of this iconic landmark. After exploring this historic gem, step just outside to experience the Chicago Riverwalk, another of the city’s must-see locales. The museum does have an off-season, so plan accordingly if this one is on your itinerary.

A local’s guide to Chicago

City markets

During the warmer months of the year (and for Chicagoans, warm is a relative term), there are innumerable markets, festivals, and street fairs. You can take your pick from a selection of events and vendors, ranging from antiques, crafts, and artwork, to fresh produce and local cuisine items. As long as you’re visiting in a month with relatively enjoyable temperatures, you should be able to find ample opportunities for outdoor shopping.

Green Mill Lounge

Chicago is famous for its own unique style of jazz music, and the great Louis Armstrong got his start in the city. This storied tradition of producing and celebrating amazing jazz musicians isn’t stopping anytime soon, and if you want to experience the music scene like a local, the Green Mill Lounge is the place to be. Once inside the walls of this bar, its atmosphere transports you back in time.

Laugh riot

What better way to slough off the day’s burdens than with some good belly laughs? Numerous comedy clubs throughout the city means you can find a place that suits your comedic taste. If improv and sketch comedy shows are your thing, Improv Olympics and The Second City are both great options. Looking for something else? There are stand-up comedians, Broadway and Shakespeare parodies, and interactive comedy shows throughout the city.

Fine doughnut dining

Exposed brick walls, deep-stained wood countertops, antique cash registers, and intimate seating arrangements… We’re not describing an upscale gourmet restaurant – this is the Doughnut Vault. Locals are crazy about this place, so much so, that the restaurant closes for the day when they sell out of doughnuts. Get there super early and snag a doughnut with flavors like pink lemonade, dulce de leche, or salted caramel (or just try one of each, no judgement).

Whatever you decide to do on your trip to Chi-town, you will not be disappointed with the offerings. No one will blame you if you want to see all the popular tourist spots, but in case you decide to hit the town like a local, the places on this list will do the trick.