Skip the Sears Tower
Chicago’s most iconic building, the Sears Tower, is overrated. Even with the addition of the new glass-bottomed balconies, $15 is a bit much to pay for a view.
Instead, head to the John Hancock Center where you can skip the admission fee by ascending to the 96th-floor Signature Lounge. Drinks are on the pricey side, but the chance to take in the views (which many feel are better than those offered by the Sears Tower anyway) from the comfort of your own seat is worth the cost.