If you are planning to go to an observation deck like the Willis Tower (formerly known as the Sears Tower) or the John Hancock Building, an elevator pass is ~$20. The BEST tip is to actually go up to the lounge in the Signature Room Restaurant. It's on the 95th floor of the Hancock Building so only a couple of floors different than the observation deck. So you can buy a drink and sit right by the glass. Elevator is free so the money buys you a couple of drinks. Much better atmosphere as well.
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