Travel Guide: Chicago, IL

Chicago, IL has to be one of my favorite cities in the U.S. It’s both contemporary and history-filled, with tons of places to see and many more activities to partake of. My sister and I took a spontaneous trip to the Windy City. If you’ve never been, here are a few places that you should definitely add to your list:


Millenium Park

Located in downtown Chicago on Michigan Avenue, Millennium Park is a 24.5-acre park and is Chicago’s center for world-class art, music, architecture and landscape design. Here, you can experience everything from interactive public art and ice skating to fine dining and free classical music presentations by the Grant Park Orchestra and Chorus. Among the park’s prominent features is the dazzling Jay Pritzker Pavilion, the most sophisticated outdoor concert venue of its kind in the U.S., designed by Frank Gehry.

Cloud Gate

Affectionately known as “The Bean”, Cloud Gate in Millennium Park is an elliptical-shaped (reminiscent of a bean) sculpture by British artist Anish Kapoor, the first of his works displayed in the United States. The 12-foot high arch provides a “gate” to the chamber beneath the sculpture, inviting visitors to see their image reflected. Don’t forget to take a picture!

The Art Institute of Chicago

If you’re looking for a way to leisurely spend an afternoon, The Art Institute of Chicago is the place to be. The Art Institute collects, preserves, and interprets works of art of the highest quality, representing the world’s diverse artistic traditions, for the inspiration and education of the public and in accordance with our profession’s highest ethical standards and practices.

If you’re interested in visiting both the Art Institute and the SkyDeck (information below), a two-for-one ticket can be purchased at either location for $47 USD.

View the slideshow below for some great snapshots of the works in the Art Institute.

The Sky Ledge at Willis Tower (formerly known as the Sears Tower) 

If you’re ever seen people take pictures in a space completely made of transparent glass, this is the place! The Ledge at Skydeck Chicago is on the 103rd floor, with breathtaking views. You are standing 1,353 feet looking straight down, with a glass boxes extending 4.3 feet out from the Skydeck. Enjoy 360 degree views spanning up to 50 miles and 4 states. The new, multimedia elevator ride gives visitors one of the fastest rides to the top ever experienced in the world, while referencing points of interest that match the ascending height. Atop the tallest building in the Western Hemisphere, Skydeck Chicago is a “one stop Chicago” experience featuring museum quality interactive exhibits.

Navy Pier

Navy Pier is a 3,300-foot-long (1,010 m) pier on the Chicago shoreline of Lake Michigan. It is located in the Streeterville neighborhood of the Near North Side community area. The Navy Pier currently encompasses more than fifty acres of parks, gardens, shops, restaurants, family attractions and exhibition facilities and is the top leisure destination in the Midwest, drawing nearly nine million visitors annually. It is one of the most visited attractions in the entire Midwest and is Chicago’s number one tourist attraction.

If you get the opportunity to go, I would certainly suggest riding the Centennial wheel. Unfortunately, most other activities during my visit were out of season and closed, but the Centennial wheel runs year-round. Enjoy beautiful views of the city skyline and of Lake Michigan at the top!


The Magnificent Mile

The Magnificent Mile contains a mixture of upscale department stores, restaurants, luxury retailers, residential and commercial buildings, financial services companies, and hotels, catering primarily to tourists and the affluent. The area also has a high concentration of the city’s major media firms, such as the Chicago Tribune newspaper, and advertising agencies. The Magnificent Mile includes 3,100,000 sq ft of retail space, 460 stores, 275 restaurants, 51 hotels, and a host of sightseeing and entertainment attractions to more than 22 million visitors annually.


Giordano’s Pizza

Giordano’s Pizza has consistently been voted the best deep-dish pizza in Chicago. Its creation began in a small northern Italian town near Torino, Italy. In 1974, on Chicago’s historic south side, Efren and Joseph opened the first Giordano’s in the world. Over the next 40 years and counting, millions of people, critics included, all Giordano’s the city’s “best” stuffed pizza! In addition to it’s award-winning pizza, Giordano also offers great starters, fresh salads, outstanding pastas and unique sandwiches.

Giordano’s is constantly making headlines, both in Chicago and nationally. The brand garners frequent media coverage and continuously tops “Best Pizza” lists and dining guides. Giordano’s has been acclaimed “Chicago’s Best Pizza” by NBC, CBS Chicago, New York Times, Chicago Magazine, Chicago Tribune, Chicago Eater, Home & Garden Magazine, Concierge Preferred and more!

Unfortunately, I only spent a weekend in Chicago, but if you guys ever have a few more days to spend, I would suggest checking off a few of these items during your visit!

Chicago Bucket List (brought to you by Sky Ledge)

  • Experience Sky Deck and get a photo on the ledge (*)
  • Try a Chicago-styled hotdog
  • Get inspired at the Art Institute (*)
  • See the city via Segway or double decker bus
  • Walk the Magnificent Mile (*)
  • Take a photo at Cloud Gate (*)
  • Fill up with a few slices of deep-dish pizza (*)
  • Glide along the river on an architectural boat cruise
  • Attend a Chicago sporting event
  • Admire the Chicago skyline from Museum Campus or Montrose Point
  • See the white Beluga walked at the Shedd Aquarium
  • Ride the Centennial Wheel at Navy Pier (*)
  • Ice skate at Maggie Daley Park’s skating ribbon
  • Catch a concert or movie at Millennium Park
  • Experience the Taste of Chicago, Blues Festival, or Jazz Festival
  • Explore the inside of a submarine at the Museum of Science and Industry

*denotes visit during trip

I hope you guys have found this travel guide helpful, and that one day you get the opportunity to experience Chicago!