City Guides

Explore the Windy City: Chicago City Guide

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Sinatra bet that you would “lose the blues” in Chicago and it’s easy to see why. One of the largest cities in the United States, Chicago mixes the natural beauty of Lake Michigan with the architectural wonders of its unique skyline.

With so many established classics, vibrant startups, food, attractions and more, it can be hard to decide what to do first when visiting the Windy City.

If you’re planning a move or a trip to Chicago, here are a few not-to-miss stops to get you started:

For the Industrious Ladypreneur

Onward Coworking
Photo via Onward Coworking.

Co-working spaces are a must-have for hardworking entrepreneurs on the go. Chicago has a gorgeous selection of both short- and long-term spaces, and Onward Coworking is no different. Beautiful exposed brick, 100-year-old hardwood floors that display the building’s character and history, exposed beams and simple design makes this space easy on the eyes. A kitchen, a variety of generously sized work spaces and a rooftop deck make it a great place to get your productivity pumping and creativity flowing.

For a Cocktail Experience

Green Mill
Photo via Green Mill

If you’re looking for a great jazz bar, Green Mill hits all the right notes. Although it is rich in history, you don’t need to be on museum behavior. This bar is classy and character rich, yet it’s also fun and friendly. Come for fantastic jazz music, signature Chicago drinks and the chance to brag that you sat in Al Capone’s very own booth – within sight of every exit, of course.

For Famous Food

Girl & The Goat
Photo via Girl & The Goat.

For fantastic food from a James Beard Award winning chef, check out Stephanie Izard’s Girl and the Goat. This Chicago native rose through the ranks of the culinary world, won Top Chef, then returned to Chicago to open her new restaurant. Her goal is to serve her guests a “family style menu of tasty, bold-flavored foods with global influence in a fun and lively setting.” Great food is accompanied by Chicago craft beers and signature cocktails. Open seven days a week, the restaurant welcomes both reservations and walk-ins. Yes, you should try the goat.

For a Shopping Spree

The Magnificent Mile
Photo via Getty Images.

If you’re looking for a spot in the city that has it all, check out The Magnificent Mile. In these 13 blocks of North Michigan Avenue – from Chicago River to Oak Street – you can find anything you want: shopping, hotels, restaurants, bars, entertainment. From Ann Taylor to Gap, Burberry to Chanel, the 460-plus shops are sure to have a few baubles to tickle your fancy. For the best experience, use The Magnificent Mile site to download a map and find up-to-date information about upcoming events.

For a Culinary Classic

Photo via Giordano’s.

No trip to Chicago would be complete without sampling its signature dish: the deep dish pizza. Although every restaurant will claim to have the first or the best deep dish pizza, few have the undisputed lineage of Giordano’s. The founders of Giordano’s brought their mother’s famous Italian Easter Pie recipe – a dish beloved by her Italian hometown to Chicago back in 1974. It has been a Chicago must-eat ever since.

For a Nature Break

Photo via Mapzio

Once you’ve had your fill of urban life, take a trip over to the Chicago Botanic Garden. Admission is free – though there is a $25 parking fee – and you have until sunset to enjoy the plants, sculptures and birds that make up this beautiful retreat.

For a … Wait, Don’t Tell Me

Wait Wait...Don't Tell Me

NPR’s hilarious news quiz, “Wait Wait … Don’t Tell Me!,” has been a Chicago staple since 1998. Attend a live taping at the Chase Auditorium and watch as panelists like Mo Rocca, Alonzo Bodden and Paula Poundstone compete under the witty judgement of Peter Sagal and Bill Kurtis to see who is up to date on the week’s news and trivia.

Sarah Landrum

Sarah Landrum is a freelance writer and career blogger. She is also the founder of Punched Clocks, where she shares advice about finding happiness and success in your career. Follow her on Twitter @SarahLandrum and subscribe to her blog newsletter for more great tips.