re: Chicago, first of April?

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Weather could be 70's or 20's

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Last three years, we've had ~25 days with temperatures 70+ compared to just 5 days below freezing. The annoying part for a visitor, especially that early in April, is planning for that one day the weather doesn't cooperate. Snow has been pretty non-existent (0.5" accumulation in three years), which is good.

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The French Market is fun to walk around one day at lunch

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Solid enough during the work week but it's just so enclosed that it feels like you're in a basement. Some of the vendors that were supposed to re-open after COVID, never did. Just a bit of a bummer because I always enjoyed walking over there before the pandemic.

For OP, Time Out might be a better option. Right in the heart of West Loop, has a full bar, ton of seating, and feels way more open. Can pop over to Guinness for a beer then walk up to Gangnam Market if he's still hungry for some food hall / market options.

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If you want a good steak, go to Gibsons or Gibsons Italia, or Erie Cafe. I've heard Jordan's is good but there are a lot of tourists.

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On the steak subject, would add Smoque Steak and Butcher and the Bear to the list if he's willing to move on the train. Butcher and the Bear has been one of the more anticipated openings in awhile - lives up to the hype, for sure. Easy hop on the Brown Line to Diversey. Also, just a great part of Lincoln Park and Lake View to walk.