First and foremost, use Search on this board and F&DB for Chicago. There are countless threads. I live here, but wife and I do not have kids. Will help where
I can but probably a few city visitors with kids that might be more helpful.

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Taking the kids to some cubs/white sox games and spending 4-5 nights in Chicago. Any recommendations for a hotel that is kid friendly (cool pool?) and is in a good location with easy access to these areas?

There are so many damn hotels, across all price ranges, in River North, Mag Mile and The Loop.

For Cubs / Sox, your best bet is to be at a hotel near a Red Line station - Grand, Clark/Division, Chicago, Lake, Monroe, etc, etc. However, and coincidentally brought it up in another thread recently, something like The Westin in River North could be perfect - they do have a pool and are in proximity of both Red and Brown Line stations. Upside is, Brown Line for a Cubs game won't be as full as Red. Get off at Belmont and walk straight up Sheffield. For Sox, don't really have another option - will need to be on the Red Line. Not that big of a deal. It's totally fine.

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Bonus points for other fun activities in the city for kids aged 5-11.

Mentioned earlier that somene else may be more helpful for a question like this, but here are some kid-friendly options: Shedd Aquarium, Adler Planetarium, top of the Willis, Lincoln Park Zoo / walk down Lake Shore trail, Logan Square Farmers Market, check out the street festival calendar (assuming you'll be here in the summer; always kid-friendly and great way to see another neighborhood outside of a very touristy downtown), and Montrose beach (great beach and bird sanctuary w/ skyline views).

ETA: Immediate area around The Bean has been under construction since late last summer. Bean is supposed to open back up in the spring, but just a quick warning since I don't know your travel dates.

This post was edited on 3/14/24 at 6:33 am