re: Going to Chicago mid-April for 4 days. Staying in Magnificent Mile area

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We love Italian, but we'll eat anything

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Rosebuds
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Met Joe Pesci there

Also love The Lodge for drinks
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We love Italian, but we'll eat anything

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Piccolo Sogno, Prosecco, Quartino, and Osteria Via Stato are near you (short cab or walk) - I really like Prosecco and Quartino...never been to the others.

Most of the super-trendy/cutting edge stuff is either in West Loop or Wicker Park. I like Avec and Blackbird in the West Loop.

Really, you could spend hours googling around for great restaurants. Chicago is neck-and-neck with San Francisco for second-best in America when it comes to food.

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Should I buy some sort of pass for the Red Line that will last a few days?

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Three days passes are $20 - you'll end up paying about $4.50 or $5.00 for a single round-trip if you take the train anywhere - not a bad idea to get a 3 day pass, especially since you can use the buses with that pass as well.

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Anything really, but I'm sure we'll be doing a lot of shopping

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Architecture tours on the river are pretty cool, and the skyline on the river is magnificent.

If you don't have any kids with you, you could just pick a patio in one of the near north or near west neighborhoods, sip on beverages all day, and enjoy yourself.

You definitely need to check out the bar at the top of the Lincoln Hotel, the J Parker. Awesome views and cool spot.

Edit to add: if you're doing a lot of shopping, hit up the stores near Armitage and Halsted - it's probably the best shopping district in the city outside the Mag Mile.