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Windy City Savings
The Travel Tightwad · April 8, 2002

Don't get blown away by high prices when you visit the Windy City. The Internet is a second-to-none resource for discounts in Chicago, and in my final column in our series on how to save money when you travel to a big city, I'll show you where to click.

First, a reality check. Even though they call Chicago the Second City, it isn't necessarily the second-most expensive city. In fact, according to a study by William M. Mercer Cos., it's the 36th-most expensive city in the world, just behind San Francisco, Los Angeles and New York in North America. So don't plan a trip here with the expectation that the bargains are difficult to come by. They aren't.

Downtown Tonight - This year-round collaboration between the Chicago Office of Tourism, Department of Cultural Affairs and more than 300 downtown theaters, clubs, cultural institutions, restaurants and stores, offers links to special events in Chicago's greater Loop, Printers Row, and Museum Campus. But what I like best about it is that you can get a free VIP card that entitles you to year-round discounts at 100 downtown restaurants, shops, and venues. I wish they'd had this when I lived in Chicago back in 1990.

Exploring Chicago - I know what you're thinking: not another "official" site. Yes, but this is a virtual path to everything cheap in the Second City, including the Grant Park Music Festival, the nation's only free municipally-funded outdoor classical music festival. As someone who spent one of the most fun summers of his life in Chicago, I can tell you that this is the best deal in town, no doubt about it. The artists are strictly A-list and the music selection is always terrific.

Hotrooms - This site seems to be the place where everyone finds the lodging deals, and who am I to disagree? You can secure special rates on just about every property in town (and some in the suburbs, too). For example, the going rate for a hotel room at the House of Blues Hotel, the well-known upscale property in downtown Chicago's Marina City Complex, is $329. But Hotroom's got prices starting at just $169. Best of all, you can book everything directly online.

Metromix - Billed as the Chicago's leading entertainment guide, this site really does live up to its name. A recent section highlighted the best brunches in the city with a special emphasis on the most reasonably-priced restaurants. You could stand on a street corner all day and ask people for the same information, but why bother when you can find it all in one place quickly? If it weren't for Metromix I wouldn't have heard out about the free performances of The Sock Puppets Perform 'Showgirls' - a revival of the box office flop in which the lead roles are played by puppets. Next time I'm in Chicago, I'm going to rush to The Side Studio on West Jarvis Ave. to catch the show. After writing an inspired series of columns like this, how could I not?

Ready to come to Chicago? If you're planning a visit, it really pays to log on and surf around for a while. Unlike the other cities I've mention in this column - Orlando, Las Vegas, New York and San Francisco - the real worthwhile URLs are often hard to find. Don't let that discourage you. Keep looking and bookmark these sites as a reference. They could save you a lot of money.

Christopher Elliott is a travel commentator based in Key Largo, Fla. All e-mailed questions may be edited, condensed or republished at the site's discretion.