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 3-4 days is good to get a feel for the ‘windy city’. But is Chicago unique and a must see city in US? May not be but if you love watching skyscrapers like I do, Chicago cannot be missed.
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 city skyline. This is one flight where a window seat is special.
Places to see
Many of the attractions are in the downtown or nearby areas. Combination of walk and public transport is fine but will require more than a day.
- The riverfront area is great for a walk/boating and for drinks/casual dining-with tall buildings dotting both sides. Plan to visit during the day a well as night. With lights on, the views are stunning. Plenty of places to sit down, relax and watch life go by.
- 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. Costs ~USD 32 per adult. 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. Entry is free but you have to pay for just about everything else!
- 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. Entry is free.
- The Shedd Aquarium. I did not visit but was told it is worth a visit. Entry cost is over USD 40 per adult.
- 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. Couple of temples as well and I visited the architecturally impressive BAPS Swaminarayana Temple. 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! Renting a car is an option but it is not needed for exploring downtown. I rented a car during my second visit in 2024 and drove on the expressway next to Lake Michigan(Lake Shore Drive), stopping at couple of ‘beaches’ and Swaminarayanan Temple. But I avoided getting close to downtown.
Rental Car
During my second visit in September 2024, I stayed near O’Hare International airport primarily because I had planned to visit nearby neighbourhoods to meet friends. Renting a car was the only economical option in the absence of convenient public transport and expensive taxis.
Renting a medium sized car from the O’Hare International airport was a breeze and it cost $150 (including liability protection) for 48 hours. The agent at Fox-rent-a-car tried hard to sell me some kind of a toll pass for~USD110. I was not sure how much toll I would end up paying but I anyway declined because the amount just seemed high. I eventually paid $24 in total, including $6 extra as I took wrong turns, getting out of expressways and then getting back in, resulting in additional tolls!
The car rental parking area at the airport was conveniently located and I could use the internal train to/from both domestic and international terminals. Adjoining my hotel (Springhill Suites) was the paid parking facility that cost ~USD25 per night.
Paying tolls in Illinois
For rental cars without transponder/I-PASS, it is very convenient to pay tolls online. I had to create an account with licence plate and provide credit card details for auto debit. The only hitch
was that it did not accept international credit cards(or forex, debit cards). Once the tolls are uploaded to the account(which could take over a week from travel date), it has to be paid
within 14 days to avoid additional fines and penalties. Good thing is that predating is possible. I created the account for the period of my car usage and got the account deleted about a month after toll payment.






