On the way to India. Stop at Chicago

CHICAGO, THE WINDY CITY

Lodging and Housing

I'd suggest to experience

Couchsurfing https://www.couchsurfing.org/n/places/springfield-massachusetts-united-states
 and Airbnb.com  https://es.airbnb.com/ 

Food and Nightlife

If possible, the must popular dish is called Deep Dish, and you should visit Giordano's Restaurant. A small pizza will be good enough for one person, and a medium size is good for 3 people. http://en.wikipedia.org/wiki/Chicago-style_pizza#Notable_vendors
If leftovers...ask for a bag to take home. 

Here is a link http://www.choosechicago.com/deals/tours-and-attractions/ of things to do. Personally speaking, I loved the BEAM!, the Illinois Museum, specially, the souveniers store, and lastly, the Navy Pier is awesome at night. Take a ride on the Ferris Wheel. 

Weather in Chicago is awful. This city is well-know as the windy city. So wrap up! 

Transportation at Chicago

In Chicago, you can either take the train, highly recommended, or take the bus. Both services are great. The rail makes a stop at the airport. 

Taking a subway may be overwhelming at first. After a couple of times getting lost, it will be the best experience ever. Especially in Chicago, the train is up-lifted!!!

Each city has its particular features. 
Follow this link http://www.wikihow.com/Use-the-CTA-Rail-System to understand How to Use the "L," "Loop" or CTA 

Official Website for schedules, maps, and faires:
http://www.transitchicago.com/

I think it's handy to have a GPS and an compas app on your celphone so you can easily determine the south and north once you drop off the train. Blocks sometimes are not at a walking distance and you would not want to get into the hussle of walking long distances in the cold.