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Willis Tower

I think taking the stairs down from the Skydeck really added to my experience - plus you’ll avoid that elevator wait. Just be ready for a little leg workout!
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!

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!

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

Check the weather before you go. A clear day makes all the difference; I went on a cloudy day, and the views weren’t great

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.

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.
Fleetwood Roller Rink

I recommend going on a weekday afternoon if you can. The place is way less crowded, and you'll have more room to skate around without bumping into people.

I suggest checking their schedule for themed nights. I accidentally went on a disco night and it was a blast, definitely added to the fun and the vibe was awesome!

I think taking a few breaks in between skating sessions is key. The place has a cozy snack area where you can chill and hydrate, just don't eat too much if you're going back to the floor.
Just For Fun Roller Rink

I recommend coming on a Friday or Saturday night for the best vibe and a fun crowd. It's so much livelier and you might even see some cool skate tricks!

I suggest bringing your own snacks if you can. The food prices are a bit steep and I found it hard to find healthy options. A backpack with some goodies can go a long way.