5 Things You Can’t Miss: Chicago

by Anthony Losanno
a river with a city in the background

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Chicago has been home since 2014. While you won’t find me at Navy Pier, I do still take every opportunity to explore the third largest city in the US.

Here are five things you can’t miss on your visit.

Architectural Boat Tour Chicago

5. Architecture River Tours

Hop on a boat and learn all about Chicago’s history and varied architecture. I’ve done the boat tours 13 times, so I’m taking a break but this is the best way to see a lot of the city’s most iconic buildings. Did you know that the Merchandise Mart had its own ZIP Code? Or, that Marina City was the first the largest federally-insured downtown housing project in the country? Take a boat ride and you’ll learn all this and more.

Can’t Miss: the boats have bars. Grab a drink while cruising.

Address: Boat tours leave from the river near Michigan Avenue or Navy Pier. There are multiple companies offering tours and all are about the same quality and similarly priced.

Art Institute Lion

4. The Art Institute of Chicago

Ferris Bueller knew this was a must on his day off and you should find the time to visit, too. The Art Institute of Chicago houses some incredible works of art. I find myself saying, “I didn’t know this was here” each time that I visit. Check out van Gogh’s The BedroomA Sunday on La Grande Jatte by Seurat, Hopper’s Nighthawks, and Mao by Andy Warhol.

Can’t Miss: my favorite: American Gothic. The ambiguous figures of the father and his daughter don’t look happy. But what’s their story?

Address: 111 S Michigan Ave, Chicago, IL 60603

The Bean Chicago

3. The Bean (Cloud Gate)

This sculpture has become a symbol of the city. Officially titled Cloud Gate, but known to most as “The Bean,” it’s been one of Millennium Park’s biggest draws since it debuted in 2004. The reflective, stainless steel surface was inspired by liquid mercury and it is constructed of 168 steel plates.

Can’t Miss: Step under “The Bean” and look up while taking a selfie.

Address: 201 E Randolph St, Chicago, IL 60602

Chicago lakefront

2. Chicago’s Lakefront

Some call it the beach and others the lake. Whatever you call it, if you’re here in the summer then you need to get some sun along Lake Michigan. Just minutes from many parts of Chicago you’ll find sand, surf (yes, there are waves), bars, running paths, restaurants, volleyball, and much more. Grab your swimsuit and join the throngs of people that pack the city’s edge.

Can’t Miss: Hollywood Beach might be known as the “gay beach” but the crowd accepts everyone and it offers one of the nicest sandy lakefront spots in the city.

Address: the beach runs along the eastern edge of the city. Hollywood Beach is located on Ardmore and N Sheridan Rd, Chicago, IL 60660

Girl & the Goat

1. Chicago’s Restaurant Row (West Loop)

It would be impossible for me to pick a favorite restaurant on Randolph Street, which is dubbed Restaurant Row between Halsted and Ogden Streets. I live here and have access to some of the city’s best dining just steps out my door. Some of my picks here include: Girl & the Goat for delicious, family-style dishes (try the goat empanadas); Au Cheval (not only for its excellent burgers but also for the matzo ball soup, Foie Gras and scrambled eggs, and blueberry muffins on weekends); Nonna’s for its What the? Sandwich with eggplant, mozzarella, chicken, and Serrano chiles; Bar Siena for a great brunch; and, Forno Rosso for its Neapolitan-style pizza (which is my favorite in Chicago and one of the best outside of Naples). That’s just on Randolph Street. Head a block north to Lake Street and you’ll find even more great eats with Proxi and Alla Vita nearby. One more block north and you’ll find The Publican, Joe’s Imports, Duck Duck Goat, Rose Mary, and many more picks. I have to spend every night on the Peloton to keep up with all of these spots.

Can’t Miss: Time Out Market offers outposts of many more restaurants under one roof with multiple bars and lots of seating. Grab a friend and dig in to everything from Indian to burgers to ramen and much more.

Address: Randolph Street between Halsted and Ogden Streets (plus the surrounding area).

Chicago offers something for everyone. From art to beaches and culture to great eats, the Windy City is a great place to visit (and live).

The Gwen

Bonus Hotel Pick: While I live in Chicago, I have been known to take a staycation and also seem to frequently have family visiting. When they come, they’re put up at The Gwen. The hotel is designed to invoke 1930s vintage glamour and it succeeds on all fronts. The Art Deco facade was crafted by the hotel’s namesake, Gwen Lux. Service, rooms, and location make it a great place to retire after exploring the city all day.

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