If you like art there is a fine museum on Michigan Ave where impressionists abound. I recommend that as well as a guided architecture tour to see a feww of the iconic buildings there. Frank Lloyd Wright s stuidio is in nearby Oak Park. The Science Museum is world famous. In it they have a Boeing 727, a train and a U-Boat.For entertainment in the evening I can recommend Second City, the breeding ground that gave us so many comedians that we know and love. Many have gone from there to Saturday Night Live. And the Blues!! Several Great Clubs. I like Kingston Mines on Halstead. Sometimes a college ID will get you in. $3 beers. Some great soul food very reasonably priced and two bands giving you six hours entertainment. Shows start at about nine or nine thirty. Rosa s is a good club as well. There is also another club right across the street from Kingston with the famous BLUES sign. Of course ther is Buddy Guy s club, BB king s and the House of Blues, but I think tha6t is more of a tourist thing.You are supposed to eat a Chicago Dog and deep dish pizza, but I think that they were both terribly overrated.
Lots of things to do in Chicago. Do a search on Chicago tourism or consult a guidebook [either printed or on line, e.g. Fodor s, Frommer s, etc.]. Millenium Park, MoSI, the restaurant/bar near the top of the Hancock building. You may have to pay for a drink, but it s cheaper than paying for the observation deck, and if you go at the right time, i.e. after lunch hour and before happy hour, you might even get the view for free. Your girlfriend should definitely check out the ladies room there! Shedd Aquarium, the Art Institute, gallery-hopping in River North, window shopping on the Magnificent Mile.If you want an amazing, adventurous, VERY expensive dining experience, try Moto. The food is molecular gastronomy , the latest fad in dining. They have a website. Dinner will be $100 each without drinks. It s a once-in-a-lifetime treat. [I was lucky enough that someone treated me!] Another interesting spot is Heaven on Seven on the 7th floor of an office building downtown [they have a website, too]. It s Cajun, etc., food in a fun setting - good place for lunch. The dirty burger is great!
Sights:(1) The Sears Tower(2) The Art Institute of Chicago(3) Marshall Fields(4) Navy Pier(5) The John Hancock Building(6) Magnificent Mile Area(7) Shedd AquariumRestuarants:(1) 312 Chicago(2) Adelle s(3) Bistro 110(4) Carson s(5) Dengeos(6) Ember Grille(7) Jane s(8) M. Henry(9) North Pond Cafe(10) P.J. Clarke s(11) Tuscany(12) Yoshi s Cafe(13) ZealousActivities:Beaches:Loyola Leone BeachOak Street BeachNorth Avenue BeachEvanston BeachMuseums:Field Museum Of Natural HistoryMuseum Of Contemporary ArtZoos:Lincoln Park ZooBrookfield ZooTheatres:Cadillac Palace TheatreSteppenwolf Theatre
Loads to do in Chicago. I would consider a road trip to Madison, WI. Great college town - http://www.tripcart.com/usa-regions/Metr��
Navy Pier, Millenium Park, Sears and Hancock towers, theaters, Zoo s, museums, many great bus and boat tours that you can take, just to name a few things.
here is a list of cool stuff i made a few years backhttp://www.listsofbests.com/list/24227