Navy Pier
Lakefront
Millennium Park
Buckingham Fountain at night is beautiful
They have free trolley rides mostly at all these locations.
If you_re looking for a really great Thai restaurant which was pretty cheap last I looked (full dinner for about $20/person), check out Pingpong. It_s on Broadway a little north of Belmont.
There_s a nice little Guatemalan restaurant at Roscoe west of Damen that_s cheap. The actual intersection is Roscoe and Hoyne. Just down the street from where I used to live.
There_s a great Mexican restaurant called Tecalitlan on Chicago avenue way out west, I want to say between Damen and Western. You can eat there with drinks for less than $20 a plate, too.
Will_s Northwoods Tavern, on Paulina and George, is a good small bar for a drink. Relatively cheap booze. I also like Fizz in that area, and they have surprisingly good food.
There is a lot going on along the lake - North Avenue Beach is the hot spot. Or head up Michigan Ave / State Street for the standard shopping.
Architectural Boat Tours are also great for sightseeing.
There_s also a list of attractions that are always free, which is a good thing to know about. For instance, the Chicago Museum of Contemporary Photography, the Lincoln Park Zoo, and Navy Pier. All free!
You can find the whole rundown here:
http://www.smartertravel.com/travel-guid��
There are other parts of the city too that are good to explore (like Pilsen), but I don_t recommend a new-to-Chicago tourist go alone, but take a local friend. Not because it_s especially dangerous, but you could get all turned around and lost.
Pick up a copy of Time Out Chicago Magazine when you get here. It lists all of the inexpensive things to do, from inexpensive restaurants, to free comedy shows, etc. and it even tells you how to get there on the bus so you don_t have to go broke riding cabs.
I don_t like Lincoln Park Zoo because so many animals die there and it isn_t kept up well. If you really want to see a zoo go see Brookfield Zoo.
You can read more about the events I recommended at the link below.
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