Not to miss

Wrigley Field

Built in 1914 and named for the chewing-gum guy, Wrigley Field - aka The Friendly Confines - is the second-oldest baseball park in the major leagues. It's filled with legendary traditions and curses, as well as a team that suffers from the longest dry spell in US sports history. The hapless Cubbies haven't won a championship since 1908, a sad record unmatched in pro football, hockey or basketball.

If they're playing a home game, you can peep through the 'knothole,' a garage-door-sized opening on Sheffield Ave and watch the action for free. Baseball fanatics can take a 90-minute stadium tour that goes through the clubhouse, dugouts and press box. Tours take place on selected weekends when the Cubs are out of town. Reservations are required.

Art Institute of Chicago

One of the world's premier museums, the Art Institute of Chicago has the kind of celebrity-heavy collection that routinely draws gasps from patrons. Grant Wood's stern American Gothic? Check. Edward Hopper's lonely Nighthawks? Yep. Georges Seurat's A Sunday Afternoon on La Grand Jatte? Here. The museum's collection of impressionist and post-impressionist paintings is second only to those in France.

More than 250,000 artworks stuff the joint, including ancient Egyptian, Greek and Roman art; Chinese, Japanese and Korean art from 5000 years ago onward; European decorative arts since the 12th century; European paintings and sculpture from 1400 to 1800; 19th-century European paintings; textiles; furniture; 20th-century paintings and sculpture; and ever-so-much more.

Friend, you're going to need a plan to make it through here with your feet still intact. While we can get you to a few of the highlights in an hour (see the boxed text, ), you'll likely want to spend far more time absorbing the wonders. Grab a free map at the entrance and design a route that will take you directly to the styles and periods that turn you on. Or rent an audio tour (around 6) from the front desk. They come in different lengths and styles, with the Director's Tour the standout for cutting to the chase and guiding you to 40 top masterpieces.

Note the museum is building a new wing for modern art, scheduled to open in 2009. In the interim, some of the modern works are disappearing from view. You might want to call or check the website to avoid disappointment if there's something in this genre that you're dying to see.

And don't forget: more artwork awaits outside. Edward Kemeys' bronze lions have become Chicago icons since they began flanking the entrance to the Art Institute in 1894; they make a popular keepsake photo. The Stock Exchange Arch, located on the museum's northeast side, is not so much a statue as it is a relic amputated from the great Stock Exchange building when it was demolished in 1972. The AIA Guide to Chicago calls it the 'Wailing Wall of Chicago's preservation movement.' On the museum's southeast side, Augustus Saint-Gaudens' Sitting Lincoln shows lonely 'Honest Abe' in his office chair. Feel his isolation?

The museum's main entrance is on Michigan Ave (where it meets Adams St). The School of the Art Institute is accessed via the Columbus Dr entrance.

There are a couple of things to check out at the main entrance. Curators often give lectures on various artists and artworks. Many talks are free with admission; enquire at the desk to see if anything sparks your interest. Also, be sure to stop in the museum store, which carries an awesome poster selection of the Warhols, Picassos and other famous paintings inside.

Sears Tower

The Sears Tower was the world's tallest building right up until the end of the 20th century. Then the Malaysians built the Petronas Towers, and Sears became a has-been. Its self esteem only got worse with Taipei, Shanghai and Dubai putting up even higher towers. Now Sears has an outright Napoleon complex. But it's still the USA's tallest building, and it's still way up in the clouds.

Its observation platform - the Skydeck - draws 1.5 million people a year who are eager to ascend the 110-story, 1454ft building (most of which is mundane office space). The Skydeck entrance is off of Jackson Blvd. Your journey to the top starts with a walk through an airport-style metal detector, followed by a slow elevator ride down to the waiting area where visitors queue for tickets. A sign will tell you how long you'll have to wait to get high. On busy days it can be an hour or longer, so this is a good time to confirm the visibility - before you invest your time and money. Even days that seem sunny can have upper-level haze that limits the view. On good days, however, you can see for 40 to 50 miles, as far as Indiana, Michigan and Wisconsin.

There's a film to watch while waiting with factoids about the 43,000 miles of phone cable and 2232 steps to the roof, and then more lines before the ear-popping, 70-second elevator ride to the 103rd floor deck. From here, the entire city stretches below, and you can see exactly how Chicago is laid out.

For those who prefer a drink with their vertigo - er, view - the John Hancock Center is a better choice.