How to Visit Chicago in One Day and Two Nights

I have visited most of the great cities of Europe and North America but it took until the third third of my life to finally visit Chicago. Because I wanted to visit Mackinac Island, I chose the 8 day “Mackinac Island” tour by Collette because it started in Chicago. Finally, I would get to see this great city even if it was only for one day and two evenings.

The Magnificent Mile

I visited in September and the weather was perfect. The Marriott Courtyard, with its Art Deco-inspired design, sits just around the corner from Michigan Avenue, the “Magnificent Mile”. Four hundred sixty stores line this wide, flower-filled boulevard. Every upscale shop imaginable resides here. This is where we spent the first afternoon.

Facts About Chicago

• 3^rd largest U.S. city
• Population 2,718,553
• Located in the heart of the Midwest
• Home to 77 distinct neighborhoods
• First skyscraper built in Chicago (Home Insurance Building)
• 26 miles of lakefront
• 26 beaches
• 58 parks and green spaces
• 7,300 restaurants
• 65 craft breweries

Palm Court At The Drake Hotel

That first evening we asked the bellman if he knew of any local venues that offered ballroom dancing. He told us to check out the Drake Hotel and we did. It was a short taxi ride to the hotel where we entered the beautiful Palm Court. A giant dried flower arrangement on the table in the center of the room greeted us.

Built in 1920, the beaux-art Drake Hotel is designated an “Historic Hotel of America” It is home to the iconic Palm Court known for its afternoon tea lounge where Queen Elizabeth II and Princess Diana once visited. In the evening it becomes dance and cocktail room.

When we arrived, couples were dancing to the live band playing on the stage. We joined in and spent a wonderful few hour dancing in this elegant room.

City Tour

The next day we joined our fellow travelers on a tour bus to see the city. Highlights of the tour included Michigan Avenue, the Wrigley Building, the Loop, the lakefront and a walking tour through Millennium Park.

A city bus tour is always a great way to get the lay of the land and figure out where you might want to spend some extra time especially when your time is limited.

Chicago Pizza

Chicago is known for its deep-dish pizza so of course, we had to try some at Gino’s East Side. Just off the Magnificent Mile, Gino’s has been one of the most popular pizza restaurant chains since 1966. The interior is unique and colorful and the pizza was delicious.

Millennium Park

This 24-acre park sits in the heart of the city.  Completed in 2004, it is a lively gathering spot for 5 million locals and visitors. It is an urban icon of beauty and culture offering free events and exhibits, film and music programs and recreation. There is also a 3.5-acre urban garden sanctuary as well as stunning architecture, sculpture and landscape design.

The Bean

Cloud Gate is a work of public art in the heart of Chicago. The sculpture is one of the world’s largest permanent outdoor art installations. Although officially named Cloud Gate, it is known as The Bean because of its shape. The monumental work was unveiled in 2004 and quickly became one of the Chicago’s most iconic sights. 

What Does The Bean Mean?

The Bean’s reflective surface was inspired by liquid mercury. This shiny exterior reflects the people moving around the park, the lights of Michigan Avenue, and the surrounding skyline and green space — perfectly encapsulating the Millennium Park experience. The polished surface also invites visitors to touch the surface and observe their own reflection, thus giving it an interactive quality.

The reflection of the sky above the park, not to mention the curved underside of The Bean serves as an entrance that visitors can walk under to enter the park, inspired the sculpture’s creator to name the piece Cloud Gate.

The Bean is 33 feet high, 42 feet wide, and 66 feet long. It weighs about 110 tons — roughly the same as 15 adult elephants.

John Hancock Center

After the city tour we had the afternoon free so we headed over to the John Hancock Center, a 100-story, mixed use skyscraper located in Chicago near the Magnificent Mile. It was originally named after one of its early developers and tenants, the John Hancock Mutual Life Insurance Co. Even though its name was changed to 875 North Michigan Avenue on February 12, 2018, it is still colloquially called the John Hancock Center.

360 Chicago

The 360 Chicago Observation Deck is located on the 94th floor of the John Hancock Center.

In addition to the 360-degree views of the city, it contains the TILT attraction—Chicago’s highest moving experience which debuted in the spring of 2014.

TILT is an enclosed, glass and steel moveable platform that holds up to eight visitors per cycle. Once safely situated inside, the platform slowly tilts outward to an adventurous angle, generating downward-facing views of Chicago – from one thousand feet above The Magnificent Mile.

Even though solid glass protects the participants, I cannot say I was brave enough to try it. My partner did and said it was not scary. To each his own!

Summary

I finally visited Chicago and am very glad I did. Even though we spent only 30 hours in Chicago, I am completely satisfied with my visit. I feel as though I experienced the flavor of the city and would readily return if the opportunity presented itself.