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This soaring tower, built in 1974 as the headquarters of retailer Sears Roebuck and Co. (who have since moved out), can be seen from almost anywhere in the city. Its Skydeck affords sensational views (see Sears Tower & its Views).

An architectural superlative, the tower offers breathtaking bird’s-eye views from its 103rd floor Skydeck, where you’ll find yourself standing on top of 76,000 tons of steel (see Sears Tower & its Views).

The city’s skyscraping superlative is actually made up of nine tube-like sections. The views are absolutely awesome: on a clear day, you can see up to 40 miles (64 km) from the 103rd-floor Skydeck.

Since 1959, Chicago’s famed Second City comedy troupe has launched such comic lights as John Belushi, Mike Myers, and Bill Murray. Actors improvize their lines in a series of skits connected by a current events theme on the cabaret-style main stage. Reservations are a must.

The El tracks are an apt symbol of hard-working Chicago, and they feature significantly in the romantic comedy While You Were Sleeping (1995). Sandra Bullock plays an El station clerk who falls in love with a handsome commuter. He tumbles off the platform, Bullock saves his life, and comedy and romance ensue.

Housed in the basement of the Chicago Theological Seminary on the University of Chicago campus, it’s fitting that this bookstore has a well-respected academic section, especially humanities and social sciences.

Upon arrival, head straight for the Oceanarium to watch the thrilling dolphin and beluga whale show. Staff trainers frequently choose children in the audience to help them reward the marine mammals with a snack after each trick. At the daily Tide Pool Touch and reptilian Animal Encounters kids can indulge their urge to lay hands on the critters (see John G. Shedd Aquarium).

The large, stylish guest rooms here offer fantastic lake, city, or river views. The hotel also has its own business center, boat dock, health club, and five restaurants. Popular with conventioneers.

This lakefront road’s low speed limit is perfect for gawping at the palatial, architecturally diverse homes that line it as you drive north to Evanston and beyond. Art buffs might like to stop at the Martin D’Arcy Gallery at Loyola University, which specializes in art from Medieval to Baroque times.

Find some of the best cruising at this vast, four-room bar with more than two dozen video monitors that highlight a different theme (like show tunes or 1980s music) every night.