From whatever means you are traveling to Chicago be it the train, plane or the bus, the first time as soon as you land in Chicago is to buy a travel pass for sufficient number of days and get as many different maps of the city as you can. You should be able to get it from any station. Now the first thing you should know is that touring Chicago is best by bus transport and a person should know how to follow the map directions to catch different buses. Some of the important places you should see while you are there in Chicago are:
- Navy Pier
- Shedd Aquarium
- Millennium Park
- Chicago Art School
- Devon Street (If you like Indian food)
- China Town (if you want to have some Chinese, Vietnamese or Korean good food)
- John Hancock (has a nice observatory at the top)
- Sears Tower (2nd biggest building in the world)
And so on, there are a lot of other places where you can go around but the above ones are the best ones. Also, a person should at least plan for one full week to enjoy all these places since they are not just sight seeing places instead they need attention and provide with a lot of fun if given time. Chicago has huge markets if you are a shopping freak and you can enjoy yourself in big malls out there.
One thing to keep in mind is, don't be hungry till late night because most of the hotels and restaurants close very early around 9 pm and it's very hard to get anything in the night. Obviously if you can find a McDonald then it's great since it's a 24 hour service. Enjoy!