One of the quintessential things to do when visiting Chicago, in my opinion, is to go to a Chicago Cubs baseball game. The White Sox are also fun, especially for baseball fans, but if you are new to the sport and want to enjoy "America's pastime", going to a game at Wrigley Field to watch the Cubs is the better choice. First, the stadium is located in a great neighbourhood and I definitely recommend getting there early or staying after the game to have a beer at one of the local bars. The Cubby Bear and Murphy’s are two good choices. Second, the atmosphere is simply fun... even for people like my wife who don't love baseball but really enjoy people-watching. Get bleacher seats if you can.
My second tip for visitors to Chicago is to take one of the architectural boat tours that go into the city along the Chicago River and out into Lake Michigan. Any of the boat tours are good but it is much more interesting to pay just a little more for the architectural tour. Chicago is famous for its architecture and the stories about the history of each building are very captivating. Both Wendella (http://www.wendellaboats.com/chicago.htm) and the Chicago Architectural Foundation (http://www.architecture.org/tours.aspx) tours are recommended.My third tip is that when in Chicago, you need to hear the blues. I am sure there are better places for pure blues music, but my two favorites are BLUES on Halsted and Smoke Daddy on Division. BLUES is a small place on the North Side, right across from another blues venue called Kingston Mines. I never have made it into Kingston Mines but I hear it is bigger with two stages and a little too touristy. BLUES is smaller and my experience always has been good. I suggest getting there a little early to get a seat. Smoke Daddy is great too, and also a good place for some barbecue. More of a diner-type restaurant with good music.
A lot of the typical tourist attractions are worthwhile, and some are not. Both the Shedd Aquarium and the Field Museum are fantastic but can be extremely crowded on weekends. Navy Pier is ok, perhaps worth a stroll or some quick dinner or to see the fireworks in the summer, but I wouldn’t recommend it as a must see. The views from the Sears Tower and the Hancock Observatory are great, but don't pay to just go to the observation deck. The better way is to go to the Signature Room at the John Hancock Building and order a drink. The drinks are expensive but you avoid the $10 price and the view is really the same. The Magnificent Mile to me is just shopping, but I am not personally a big fan of shopping! I do recommend walking to where Michigan Avenue hits the river… the views are great. Taking a run or a walk in Lincoln Park is worth it if the weather is good.A few small travel tips… traffic to O'Hare during rush hour is terrible and you are much better taking the "L"... Chicago's subway named the "L" because it is in many cases an elevated train. You definitely don’t need a rental car in the city... taxis, public transportation and walking will be enough.
Metromix is a good site that covers things to do, restaurants, movies, sports and music. http://metromix.chicagotribune.com/The best thing I can say about Chicago is that those who live there are more proud of their city than any other city in the United States. Even in winter. Have fun!
Alan
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