With citypass the line is smaller.
As far as I remember it is the same price no matter if you shop online or right there. Where you can save is if you buy the Chicago city pass that includes other attractions besides the Willis tower. I went in February but I didn't want to go up because those days it was cloudy and snowing and the visibility was really bad. It depends a lot when you plan to go to know if you will line up to buy tickets.
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