Chicago is a great place to see. I’ve always told people that it would be great if I could make my money in New York and spend it in Chicago. I’d say Chicago is roughly two thirds or three fourths of what New York City prices usually are. If you pay $45 for dinner for two in a modest restaurant in New York City, it will cost you about $35 in Chicago. A drink at a hot spot in NYC may cost up to $10. IN Chicago it will be up to $8 in the typical hot spot. The regular establishment in NYC will charge about $3.50 to $6 for a drink in NYC and Chicago will cost about $3 to $4. I think you get the idea. (Rent, charters, cabs, taxis, tours, and shows are also priced less than New York CIty.
If you are looking for tickets to see a show in Chicago, you can find them in many places. Check out the Chicago Reader for show times and ticket deals. When in Chicago, you can see many of the great plays and Broadway shows that have run in New York CIty.
I would almost have to say that, any website or guide to Chicago (including this one) is almost irrelevant and obsolete. Why? All you have to do is pick up a copy of the Chicago Reader when you are in Chicago. This newspaper/magazine has everything you need to know about what is happening in Chicago. You can get a look at it right now online if you want, right here.
Places to see: The Chicago River (take a boat tour), Lake Michigan, the Sears Tower, the John Hancock building, the Adler Planetarium, Art Institute of Chicago, The Improv, the Second City Theater, Kingston Mines (famous blues club), Michigan Avenue by the lake, the Navy Pier, Lincoln Park and more.
What I would say to anyone going to Chicago is this. You have to see blues and you have to see jazz. If you don’t, then you are going to a city famous for both and therefore missing out in a big way. It would be like going to New Orleans and not seeing any music. One of the great things to do in Chicago is rent a bicycle (not good for winter though) on the lake front and ride it anywhere you want along the lake. You can return in or leave it off in many different locations making it fun but not a chore finding a return spot or having to bike all the way back. I usually rent a bike in the Lincoln Park area by the lake and ride all the way down to the navy pier where I leave it off. I believe it costs around $15 to $25 but absolutely worth every penny.