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Three Perfect Days in Chicago—Day One

Every year my colleague and I take a group of our college students to a city to uncover its history. This year, we went to Chicago to explore the history of the 1893 World’s Fair and the architecture of the city. In this series, I’m going to take you through my version of three perfect days in this city—immersed in its history and its culture. The series will highlight places to visit in Chicago for a fun weekend getaway. After experience Chicago tourism for years, I highly suggest that you visit Chicago soon!

Where to stay: Chicago hotels are top of the line and are frequently less expensive than other major US cities. I adore the Palmer House Hilton (17 E. Monroe). Built in 1873, it’s a historic hotel with grand public spaces, rich decorations, and lots of ambience. The frescoed ceiling of the main hall is breathtaking. Don’t miss the Tiffany-designed Peacock door off the Monroe street entrance, it is a stunner. The beds are comfortable and each room is nicely appointed, although some of the rooms are quite small. The location holds great appeal—located in the Loop, it is walking distance to many of my favorite historical sites. Staying here I feel truly immersed in the history of Chicago as I ponder the important people who have dined and slept in the establishment.

Day One

Morning—Walking around the city is a great way to see its buildings and experience its past. Many of the wonderful places to visit in Chicago can be seen on foot. Walk around the city and explore the vast art and architecturally-rich buildings. Most of Chicago burned to the ground in the Great Fire of 1871. After that, Chicago architects designed a city that conveyed an image of greatness, elegance, and charm. In the late 19th and early 20th century, Daniel Burnham (lead architect of the 1893 World’s Fair), John Root, Louis Sullivan and many other architects added to Chicago’s magnificent offerings. Today, one can view works of art in the open-air and stroll down streets lined with architecturally important buildings. To get oriented to the city, I suggest that you start your trip with the following walking tour.

  • Start at the arch of the former Stock Exchange Building. Although the building has been torndown, the Louis Sullivan-designed arch stands proudly behind the Chicago Art Institute on Nichols Bridgeway (corner of Millennium Park and Columbus Dr.). Sullivan built the arch in 1893 as a magnificent entryway to the financial institution. He thought that main entrances needed to attract attraction and express monumental importance—this arch does both.
  • From the arch, you are on the edge of Millennium Park. The gardens and artwork in the park are a treasure. Don’t miss an opportunity to take your picture in the “Bean” (Cloud Gate by Anish Kapoor) or splash around in Crown Fountain by Jaume Plensa.
  • Start walking north on Michigan Avenue. Up ahead on your left, you should see a neo-classical building that says “Chicago Public Library” (78 E. Washington). Now the Chicago Cultural Center, the “People’s Palace” is not to be missed. The entrance on the Washington side will take you into the former library—a celebration of learning and humanism. The lobby features a grand Italian Carrerra marble staircase with accents of dark green Irish Connemara and an arch inscribed in jeweled mosaic of the names of great thinkers. Everything about the staircase screams that treasures (books) abound here. The staircase opens into Preston Bradley Hall where people used to receive their books and read them. There is a dome made of Tiffany glass—the largest of its kind. Surrounding the hall are quotations in various languages that inspire learning and honor the many cultures of the immigrants who came to work in Chicago. On the other side of the building is a memorial to the Union soldiers of the Civil War. Dedicated by the Grand Army of the Republic, the opposite hall is somber and sedate. It, too, has a stained glass dome (designed by Healy and Millet), but its hall, decorated in green Vermont marble, reminds us of the horrors of war. Spend some time at the Cultural Center, if you wish, they have neat exhibitions and lots of events (as well as a tourist center).
  • Once you step out on Michigan Ave., continue walking north towards the river. On your left, you will see the Carbon and Carbide Building (230 N. Michigan)—an art deco skyscraper designed by Burnham Brothers. Coming up on the right is the Fannie Mae candy store—I can’t resists their sea salt caramels and maple walnut butter creams. Mmm. Across the carved Michigan bridge, is the last stop on the tour—the Chicago Tribune building (435 N. Michigan Ave.). This neo-Gothic building designed by Howells and Hood was completed in 1925. Pieces of prominent architecture, like the Great Wall of China, are incorporated in the building and allow viewers a chance to travel the world.


By this time you are no doubt hungry, so I would suggest taking the metro up to Wrigley Field and enjoying a hot dog and Cubs mania. If you’re lucky, there will be a game to catch and you can sit in this historic stadium and enjoy a 100 years of baseball history.

Early evening/Dinner

After stopping back at the Palmer House to freshen up—and maybe take a little nap—I enjoy taking the Shoreline Water Taxi for a tour of the Chicago River. Starting near the former Sears Tower (now Willis Tower), the taxi takes you for a leisurely cruise up to Navy Pier where you can enjoy a Ferris Wheel (of 1893 World’s Fame) that overlooks Lake Michigan. Although a little too touristy for my taste, Navy Pier has a beach, lots of activities for children, bars, and restaurants. If you walk to the end, you have a gorgeous view of the Chicago skyline, lighthouses, and one of the greatest lakes in the world.

You’ve earned your dinner now, so I would recommend a hearty Midwestern meal of carbohydrates. I like Eataly (43 E. Ohio), which consistently has fresh pasta, authentic pizzas, a huge selection of vegetarian dishes, fish, meat, and more. Feeling virtuous for walking so much, I would go ahead and have gelato for dessert. This ends my first perfect day in Chicago. Stay tuned for day two!

Check out our fabulous photographic prints on our Etsy shop for yourself or as a gift.

Water view of Chicago Tribune
Water view of Chicago Tribune
Tiffany Dome, Chicago Cultural Center
Tiffany Dome, Chicago Cultural Center
Hot dog in Wrigleyville
Hot dog in Wrigleyville


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