A Day in Chicago: The Insider’s Guide


When it comes to travel, it’s nice to have an insider’s perspective. Here at Blueprint, presented by CBRE, we are fortunate to have an expansive network of local colleagues around the globe who are not only real estate experts, but also local tastemakers. We have asked them to give an insider perspective to some of the best, most iconic cities across the globe. Today we explore Chicago, Ill.

City: Chicago

Country: United States 

Nicknames: The Windy City, the City of the Big Shoulders

Population: 2.7 million


What is your favorite public space? Why?

Chicago’s lakefront. You can rent a boat for the day and get a rare view of Chicago’s skyline. If you get tired of that, you can take the boat through the lock and down the Chicago River to get a quick snack at the new Riverwalk. If boating isn’t your thing, take a walk at Alfred Caldwell Lily Pool. There is a secret entrance into the Lincoln Park Zoo there as well should you fancy seeing some animals. Lastly, Foster Beach at the north end of Lake Shore Drive is a must-visit. A small area is designated for pets, perfect for your furry friends.


Where can you find the best view of the city?

The Terrace at the Trump Tower. This rooftop lounge at the tower is tucked away from typical tourist attractions. It also gives you an intimate view of the Wrigley Building, the Tribune Tower, the Chicago River and the easternmost side of Wacker Drive. If you’re afraid of heights, driving south on Lake Shore Drive towards the city never fails to delight.


You are going for a bike ride. Where do you go?

Rent a Divvy bike and ride the Chicago Lakefront Trail. It runs 18 miles along the coast of Lake Michigan from Lincoln Park to Jackson Park. You can stop by Museum Campus, Soldier Field, Navy Pier, most of the Chicago beaches and three skate parks.

What is the best place to discover local music?

Studio Paris is the birthplace of house music and is still Chicago’s premier venue for local DJs to get their start. If you prefer jazz, the prohibition era and Al Capone, go to the The Green Mill in uptown Chicago. Previously a speakeasy during the Roaring ’20s, it has been played by Chicago jazz legends such as Von Freeman, Franz Jackson and Wilbur Campbell. 

What is the “don’t judge a book by its cover” restaurant?

La Scarola in River West is a hole in the wall but has some of the best Italian food in the city. Come for the food, stay for the atmosphere. Head to The Violet Hour if you want the best cocktails in town. Then there’s Tank Noodle. At first glance it may look like your standard restaurant, but once you taste the pho you’ll know then that you’re somewhere special.

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Favorite place to watch a game?

The Wrigley Rooftops. (Need we say more?)

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Best public transportation experience?

For $10 you can get an all-day pass (on weekends) for the Chicago Water Taxi to see the entire city from the Chicago River and Lake Michigan. Or take a horse and carriage ride on Michigan Avenue.

Favorite place to unwind?

To truly unwind in the Windy City, follow this recipe: Start with an intense class at Core Power Yoga to stretch (and sweat) the stress away. Have an early brunch at a café table at Eataly. And finish with an evening at Three Dots and a Dash for a tiki drink.

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Favorite place to be inspired?

The Art Institute of Chicago. If it worked for Ferris Bueller, then it can work for you.


Best place to be alone?

Northerly Island Park is a 91-acre peninsula that extends into Lake Michigan. The majority of the space is dedicated as a natural area, with walking paths and recreational areas.

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Best place to feel like you’re not in your city?

Green Street Smoked Meats. The BBQ there is as good as any you’d get in Austin, Tex., or Memphis, Tenn.

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Best insider place to take the kids?

From tornadoes to Tesla coils, the Museum of Science and Industry brings learning to life with hands-on exhibits. With unique experiences like an underground tour of a coal mine, a German submarine and a baby chick hatchery, it has exhibits to amaze children (and adults) of all ages.

Best independent shopping venues?

RSVP Gallery on N. Damen Ave is much more than a retail space. Built by local Chicago artist and self-proclaimed “brand architect” Marc Moran, the store was designed as “a space that carried the rarified air of an art gallery, but still gave off the warm, welcoming feel of an intimate retail boutique.” We think he nailed it. 

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Best Hidden Gem Museum?

Chicago is a city with a rich history ranging from disaster to triumph and everything in between. To truly appreciate Chicago, we recommend visiting The Chicago History Museum, which showcases millions of pieces of Chicago and U.S. history.

Best place to get a local specialty?

Well, that depends on whether or not you’re on a diet. The donut ice cream sandwich at Firecakes Donuts is worth whatever impact it may have on your figure. The “dreamsicle” cake from Brown Sugar Bakery lives up to its name. The Koval Distillery makes some of the finest whiskey in the Midwest, and it also offers cocktail classes and whiskey workshops.



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