chicago is a beautiful city, to me personally, one of the most beautiful big cities in American continent. a few things worth you take a peek:
1. the lake Michigan is so beautiful, it is giant and it water color changes all the time because of the weather and seasons. the city has built a route near the city for walk or bike; it is worth to take a long walk there. the scenes of those high-rises and the lake change. it could take you a day if you want.
2. chicago is famous for its architecture. a lot of modern architecture revolutions were developed here (due to a 19 century city fire burned down the city entirely, except the water facture which you still can see in the famous Michigan Avenue-the American so called magnificent mile, similar the 5th avenue of NY, where you can go shopping). To tour the architectures you can join the boat tour which is organized by the architecture society...plus, i recommend you explore those building not just see those building outside but walk in...you will see the decorations inside are so different and beautiful, for example...diffent building use different marbles...walk in to have a look, that is the best way to explore a city, of course, it fits for the weekdays, not weekend. Most buildings closed during weekend. chicago harbored a few dozen F 500 company headquarter, worth to walk in to take a peek, hehe...but watch your dress. do not act like a tourist ...hehe.
3.chicago is a big city so it has all those things can be enjoyable in the city: museums like chicago art institute, field museum...and more, chicago art institute is not as good as metropolitan museum of NY, its level is among those second tier museums like those museums in DC's museums like American art G. and etc. Tuesday is free. Shopping you can go to Michigan ave., and state street, if you like jewelries, go to Wabash(?), you can find a lot of barging there. a lot of good famous restaurants (it is pity mostly are not chinese). During night, a lot of shows you can go to, like the "Goodman theater" was just finished its renovation and ...other than that, you can go to various bars or night clubs for the night. But if you go to those Southside of them, be aware of the safety, south of the chicago have more color of black, not all, some place have "jungle" out there. financially, chicago has the largest future and option exchanges of the world, just like NYSE, you can have a tour. And a lot banks
Anyway, good luck! I feel tour chicago should use the same way tour NY, have your gym shoes on, walk around and have fun, tired then sit, hungry then eat (although ny is big, ny has both down town and up town worth to explore, chicago only down town is good, uptown has nothing).
