The best way to spend 3 days in the Windy City.

Secret Stacy
Sep 12 · 6 min read

Of all the bucket list large cities in America, Chicago is my favorite. The Windy City sits on the beautiful beaches of Lake Michigan, just south of the Wisconsin/Illinois state line. It boasts beer, music, art, architecture, and an unbelievable array of world class cuisine. Chicago has the New York vibe for less money without the trash, scaffolding, and traffic. Making it the perfect place for a quick big city getaway.

Navy Pier — All pictures courtesy Secrets From the Real World

Day 1: The View From the Top

Chicago has a unique architectural feel. It was founded a little over 200 years after New York in 1833. So the city is relatively young compared to many other major US population centers. That means the design elements of the buildings that make up the downtown Chicago area are much different than the older buildings in other cities. Chicago is sometimes called a “concrete jungle”, and that’s precisely how many of it’s towers were erected. With concrete structures.

The elevated train, the Gothic stone tracings, and heavy white walls lining the city streets give Chicago a distinct Gotham feel. (Many of the Batman movies were filmed on location in Chicago.) One of the most pleasurable things to do in the Windy City is to enjoy the uniquely beautiful views.

Chicago features 4 of America’s top 10 tallest buildings; (Willis Tower, Trump International Hotel, the Hancock Building, and the Aon Center) so you can be sure there is no shortage of beautiful viewing areas.

Terrace 16 at the Trump International Hotel

Check into your hotel, then start your first evening in Chicago with a toast, watching the sunset from the 16th floor of the Trump International Hotel overlooking the Chicago River-walk. There isn’t a bad seat in the house, the Terrace 16 restaurant has an outdoor lounge area with plush couches, fireplaces, and a clear railing, allowing unobstructed views on three sides of the building. (Don’t forget a sweater, it does indeed get very windy.)

After you’ve properly toasted to your trip, have a walk around the Riverfront area to Giordano’s Pizza in downtown. A Chicago style pizza is something you can’t skip, and Giordano’s is a hands down favorite for locals and tourists alike.

Once you’ve had your fill of pizza. (A small can feed four adults.) Try a night cap at a Chicago speakeasy bar. (Chicago has many hidden bars, some of which were in operation during prohibition.) The Watershed is located in a tiny basement in downtown with a small, unique, yet opulent atmosphere, and fantastic service.

When dinner, drinks, and desserts have been had; it’s time to call it an evening and get rested up for your second day of adventures in the Windy City.

Day 2: “Art speaks where words are unable to explain.” -Anon

Chicago features some of the most amazing art you’ll see, paintings, theatre, sculptures, and architecture; this city has it all. Start your second day with brunch in downtown at The Gage, an upscale bistro that serves one the best cheeseburger you’ll ever taste.

After brunch, cross the street to Millennium Park. There’s always plenty to see and do in this public square. Take pictures in front of Cloud Gate, (Also popularly referred to as “The Bean”.) admire the sculptures and fountains, eat a Chicago style hot dog, the park features flower gardens, music, and a host of events.

Once you’ve seen it all, head inside The Chicago Art Institute for a live look at dozens of world famous paintings. At $25 per ticket, The Art Institute may not be the cheapest stop on your trip, but it’s still worth every penny. A large collection of Degas, O’Keefe, Da Vinci, van Gogh, Monet, Sauret, and others adorn the walls in the maze of museum. Lose yourself in the history and beauty. (But also get a map at the information desk, because you really can get lost.)

Vincent van Gogh’s Self Portrait (Much more colorful in real life than in the school books.)

Once you’ve had your fill, head back to your hotel to rest, refresh, and spruce up for an evening of fine dining and theatre.

Get fancied up for dinner at Joe’s Seafood: Prime Steak and Stone Crab. The food is something you can’t experience anywhere else. The tuxedo clad service impeccable. (You’ll want to make reservations well in advance.)

Finish your evening with a show you unlike any other. Chicago has a theatre scene that rivals New York’s Broadway. Get tickets in advance if you like for any shows on the calendar, or try Lucky Seat the day before and gain entry for half the price (or less).

Day 3: Fun in the Sun

“Beach” may not be what first comes to mind when you think, “Chicago”. But don’t sell your trip short. Chicago has beautiful beachfront areas on Lake Michigan. Start your day on Montrose Beach. Play in the sand, soak up the sun rays, rent a paddle board and enjoy your morning on the water, with the Windy City skyline as your backdrop.

After you’ve worked up a proper appetite, grab lunch at The Dock, a beach front outdoor dive bar that sits in between the city, the beach, and Montrose Harbor.

When lunch is finished, call an Uber to deliver you to Navy Pier. Take an architectural cruise, have a ride of the iconic Ferris wheel, shop the local vendors, and be sure to have a cocktail at Offshore Rooftop Bar, with see through banisters, couches, fireplaces, and outdoor family style games, it’s the perfect place to relax and recount the amazing experiences you’ve had over the past three days.

Stay long enough to appreciate the sunset, but before leaving for your flight home, make in one last stop, visiting the Hancock Building’s Signature Lounge for coffee, cheesecake and a breathtaking view of the cityscape from above at night.

Downtown from The Hancock Building’s Signature Lounge

Before you depart for O’Hare, be sure to visit the restroom. The women’s lavatory has an entirely glass back wall, boasting one of the best views in the building. Watch the planes in formation, waiting their turn to land at O’Hare, the Ferris Wheel on the pier turning, and Willis Tower blowing slightly in the wind. The Hancock building is the perfect cap to a delightful getaway in one of America’s brightest big cities.

Have a location you’d like us to travel to? Let us know, you might find us visiting on an upcoming trip!

Secret Coran-Stacy is an author, entrepreneur, and artist living the dream as a middle class suburbanite in Central Arkansas. Find out more by visiting

Secret Stacy

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⭐️Life and Politics Contributor @citizensource ⭐ Author ⭐️ Entrepreneur ⭐️ Conservative ⭐️ Lover of the American Dream ⭐

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