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Chicago is a city of choices: you can splash out on the fanciest meals and pricey theater tickets or opt for fun activities that don't cost a dime.

If you plan to hit several major attractions, consider a Chicago cityPASS at participating locations or online (www.citypass.com/chicago). It will save you a combined total of about $80 on admission to these major attractions: Shedd Aquarium, the Field Museum, Skydeck Chicago at Willis (Sears) Tower, either the Museum of Science and Industry or John Hancock Center Observatory, and either Adler Planetarium or the Art Institute of Chicago. To save even more, time your museum visit for a day or time when admission is free.

From spring to fall, neighborhood fests and free concerts abound. The most stunning place to catch a free concert is the Frank Gehry–designed Jay Pritzker Pavilion at Millennium Park. Daytime and evening concerts showcase everything from classical to jazz to punk rock.