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Willis Tower
I had the best time taking pictures on The Ledge, but it’s super popular, so make sure you keep an eye on your time to snap those shots before it gets crowded!
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I suggest going on a weekday if you can. The lines are way shorter and you can really take your time enjoying the views without heaving crowds everywhere!
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My advice is to check the weather before you go. A clear day is the best for those skyline photos. Nobody wants a foggy view!
John Hancock Center
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I recommend visiting the observation deck right when it opens at 9 AM. It's way less crowded, and you can enjoy the views without fighting for a spot.
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grab a drink or snack at the café up there; prices are steep, but it's a great way to soak in the view while you recharge.
My advice is to take your time on the observation deck – don’t rush through it. The sunset views are stunning if you can stick around until then.
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I suggest taking the elevator up during off-peak hours if you can. I went around lunchtime, and it was packed – waiting was a hassle!