Spinoff...Chicago

Solid location. Don't spend much time downtown unless I am at work during the week, but...

A drink or two at Cindy's on the rooftop of the Chicago Athletic Association then going to dinner at The Gage is never a bad choice. Neither is particularly cheap, but quality stops and close to the Palmer House.

Other than that, I would recommend venturing outside of The Loop for food and drinks.

The Red Line station at Monroe can take you north (Howard) to Addison for the Cubs and south (Dan Ryan / 95th) to Sox-35th for the White Sox. The Blue Line station at Monroe can take you north (O'Hare) into Wicker Park or Logan Square. If you want to go to West Loop for restaurants, etc., you can easily Uber or take a Pink/Green Line train from Adams/Wabash. The Brown Line to Kimball runs a, somewhat, similar route to the Red Line going north and is also on the elevated tracks at Adams/Wabash.

ETA: How are you planning on getting to Milwaukee? Union Station isn't more than 15-20 minutes from Palmer House. Hop the Hiawatha (Amtrak) for 1.5 hours and less than $30. Miller Park is a very fun spot to tailgate. You can Uber from downtown or take a bus.

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Revival Food Hall- it's basically an upscale food court of local Chicago restaurants. Highly recommend.

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Good call on Revival. Caters to the M-F crowd, so it's actually closed on Saturday and Sunday, but now that I looked at OP's post, looks like both games he'll be at are at night during the week. Revival would be a good spot to grab a bite before taking the train north and/or south.

Actually have a rental from Chicago to Milwaukee. Buddy of mine goes all out for these trips. He got a hummer for the whole group to surprise the boys. Some special rental with the Lamborghini doors. There's 12 of us total...5 dads and 7 boys ranging from 10-15. Will definitely have lunch at Revival one day.