48 Hours In Chicago, Illinois

Above: Chicago’s famous Cloud Gate Sculptureby Indian-born British artist Anish Kapoor. The public sculpture is the centerpiece of AT&T Plaza at Millennium Park in the Loop community area of Chicago, Illinois
Above: Chicago’s famous Cloud Gate Sculptureby Indian-born British artist Anish Kapoor. The public sculpture is the centerpiece of AT&T Plaza at Millennium Park in the Loop community area of Chicago, Illinois

Chicago is one of the most popular tourist destinations south of the border and it’s easy to see why. Have you seen that picturesque skyline along the waters of Lake Michigan? Chicago is a huge vibrant city, the third largest city in the United States. Here’s everything you need to know before booking your next trip there.

What to do?

Chicago has a vibrant theatre scene and numerous museums that are worth checking out – the Field Museum, the Shedd Aquarium, the Art Institute of Chicago and the Museum of Science and Industry. If you are there during warmer weather be sure to check out Navy Pier and take one of the architecture tours on the water. Of course, this city is home to some great baseball, hockey and basketball teams, which are sure to satisfy all the sports fans.

Where to eat?

This city does Brunch well. Be sure to check out Lula Café in Logan’s Square or The Southern in Wicker Park or Mon Ami Gabi in the Lincoln Park area. For lunch, we would suggest hitting the Chicago Eataly outpost or The Purple Pig.  There are far too many amazing dinner choices (yes, there are options other than deep dish) and there are some stand out places you should really try – The Girl and The Goat moved into the West Loop and changed the foodie scene there forever. It is still a must on everyone’s list. But when you are in the loop be sure to check out Publicans, or Green Street Smoked Meats (amazing BBQ). Logan Square also has great choices with Longman & Arrow, Analogue and Scofflaw

Going out?

This is a city that offers a variety of going out options depending upon the neighborhood you are in.  We suggest wandering outside the downtown core, Golden Mile, to experience the city as locals do. River North is a neighborhood just outside the core; be sure to check out The Drifter (a modern day speak-easy hidden in the basement of the Green Door Tavern) or Stout Barrel House if you’re looking to watch a sports game. Head over to Wicker Park for some great craft cocktails at The Violet Hour or check out Rainbo Club for cheap draft (a converted Polka Bar – aka a bar even too hipster for hipsters).  The West Loop offers a relaxed vibe at the Lone Wolf or if a champagne lounge is more up your alley, check out RM Champagne Salon. The real hipsters have left Wicker Park (blame the gentrification – Mar Jacobs store and all) and have gone to Humboldt Park where you can find a classic joint called California Clipper or Sportsman. If you want to still drink after 4am, you can find places in this ‘hood to do so – Continental is the go-to for after hours drinking. The last neighborhood worth checking out is Logan Square with some great locals including Emporium (a huge space with pinball machines, arcade games and a pop up food truck inside), Slippery Slope (a classic dive bar turned hipster bar), The Whistler and The Owl. Oh yeah, this city also seems to be all about the new tikki bar trend – Three Dots and a Dash is the classic (enter through the back alley) and Lost Lake is the newcomer on this scene. Just be sure to check what time is their last call – it seems to be different per bar and neighborhood.

Where to shop?

The Golden Mile is known as the place to shop if you want to hit all the designer boutiques and department stores. Just make sure you wander slightly off Michigan Ave if you want to discover Saint Laurent, Barney’s New York and Jonathan Adler. Head over to Wicker Park to find Marc by Marc Jacobs, a TOMS outpost, Goorin Bros, and for sneaker aficionados there is Stash.

Where to stay?

The hotel options in this city are endless – there’s a Waldorf Astoria, a Trump, a Thompson, a W hotel… But be sure to check out the newly opened Virgin Hotel for something a bit different.

Christian Dare

Christian Dare

Christian Dare spent much of his formative years working in the fashion industry as a Visual Manager before pursuing a Masters’ Degree in Design. He is the Principal at Christian Dare Creative, the co-founder of Stylist Box and runs a successful men’s lifestyle blog, Christian Dare Edited,focusing on menswear, interior design and craft cocktails. You can find him online at www.christiandareedited.com or follow him on Twitter @christiandare but he is more fun on Instagram christian_dare. 

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