There are plenty of great threads and information on Chicago on this board. Some really great knowledge.

I copy and pasted some of my older posts.... but def use the search bar and just type in Chicago and dive in!

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Obviously I’m trying to compress a lot into too little time, but tell me if something seems way off.

Sure, but at the same time you'll always be able to do MORE in Chicago. Just so much to do. So don't feel like you didn't get the trip right. Make the most of what yall have planned and enjoy!

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Would you be worried about the safety of the blue line from Ohare to downtown in midday?

Usually fly SW, so come from the Southside and usually anyone from the airports are all the same crowd. So def not too sketch. Should have no issue.

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Is there a particular section of the river walk you recommend?

I'll let others chime in, but the riverwalk really isn't much. We enjoyed Happy Hour at TinyTapp with some live music and relaxing right there, but its not much more than just walking and taking in some sights.

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It’s supposed to be in low 60s with a 10 mph East wind with a rain possibly. How cold is that going to feel to South Louisiana folks?
I know we shouldn’t wear shorts, but do we need jackets/hoodies IYO?

Shorts and a light jacket is perfect. Dress comfortable. If you're doing the amount of walking etc. it's good not to have all those extra layers on and you won't sweat. You'll just enjoy the temps and the sights.

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I guess I left off walking the Mag Mile.

Yeah, they have plenty of stops on Mag Mile that teens would like and enjoy + the sights obv. My 12 year old enjoyed the Nike Store (4-5 levels), and other shops on Mag Mile.

***I always add this in here but the Chicago Athletic Association is always a fun stop. Took my son there, played some pool and other games. Great architecture and great vibes. They'll enjoy. Not far from the Bean etc.

They have a nice rooftop spot that overlooks The Bean called Cindy's there. Altogether a really cool spot/stop. I've been to Chi 3x now and every time I pop in.