The third largest city in USA is a multi-faceted city
The United States is a huge country. Whenever foreigners think of US as a holiday destination, the locations that come to mind readily are New York, Washington DC, Niagara Falls, Florida, Las Vegas and the Grand Canyon, San Francisco and Los Angeles. Chicago is not really on the list but this city too has its own charm. I would think 4-5 days is good to get a feel for the ‘windy city’. But is Chicago unique and a must see city in US? I am not so sure.
Located on the banks of Lake Michigan, it rivals New York when it comes to skyscrapers. It is called the windy city but I am not sure why? It was far from being windy while I was there in the month of October. I thought San Francisco is windier than Chicago! But yes, Chicago can get very cold in winters. Last winter, Lake Michigan froze and the temperature in Chicago was lower than that in Antarctica. Chicago is not the place to visit during the long winter months(say November to April).
Just before landing, my flight flew over the city, and then over the Lake Michigan before taking a turn towards the airport. Great views of the skyscapers and the Lake.

Places to see
Many of the attractions are in the downtown or nearby areas.
- The riverfront area is great for a walk/boating and casual dining-with tall buildings dotting both sides,
- the Willis Tower has an observation deck on the 103rdfloor(~1350 ft) that offers expansive views of the city. There is glass deck that extends 4 ft out. Generally crowded.You can book online to save time in the ticket counter queue. The question is – day or night or both? The alternate is John Hancock Building.
- the Navy pier with its rides, shops, restaurants etc is great for families,
- the Millenial park with the mirrored, bean shaped sculpture. Though a bit long, one can walk from Millenial park to Buckingham fountain and Grant park.
- The Shedd Aquarium
- Michigan avenue, a very attractive boulevard. The Magnificent Mile, the famous shopping destination, is a section of Michigan avenue. Largely branded stores and hence can be skipped.
There are other places of interest-museums, including the Art Institute of Chicago that opened in 1879….this is where Swami Vivekananda delivered lectures at the World’s Parliament of Religions in 1893, Brookfield Zoo, Adler Planetarium, the deck on John Hancock Building, beaches, Lake Shore drive, The Little Italy, Greek Town and Chinatown. For the academically inclined or families with teenagers, Chicago is home to Northwestern University( famous globally for Kellog school of management) and University of Chicago. Visiting campuses is always inspiring.
Depending on your interests, buying a city pass will help you save on entrance fees. Taking the hop on hop off bus is also a good way to see the city. Public transport-a combination of trains and buses-is also an option. Taxis will be expensive but convenient for point to point commute. I preferred a mix of taxis and my feet!