Chicago, first of April?

Google “Chicago restaurant recommendations tigerdroppings” and there are some really great threads with a ton of good options. Personally I wouldn’t go to Michael Jordan’s steakhouse with so many other better options.

-Field Museum is solid
-Boat architecture tours are awesome; weather in April probably won’t be great though
-Chicago Art Institute gets a lot of love
-Stroll around Lincoln Park and the Zoo
-Cubs are in town playing the dodgers that weekend. Definitely recommend catching a game from the outfield bleachers

For weather April it likely won’t be great but you could get lucky. The times I’ve been in April it’s consistently been windy, rainy, highs in the 50s maybe 60s

Weather could be 70's or 20's. Check the day you leave, bring options like sweater, vest, coat. Don't bother with flip flops because the chances of rain or snow are very high so think good all-weather shoes. It is a walking city.

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.

I hate touristy stuff but check out the Sears Tower, it is really high up. Also live hockey is great, a Hawks game could be fun.

The French Market is fun to walk around one day at lunch. If you are into comedy, Second City is great fun for the money.

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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.

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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.

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I'm sorry to hear that, too. I lived in town for quite a while and really enjoyed Saigon Sisters and the Belgian Fry Stand. There wer probably 5-8 good places to have lunch in there and the whole family could really pick and choose.

I do know what you mean about the basement feel, that is absolutely right. Especially back where the tables are. Not a great vibe.

Don't go to Michael Jordan's. I'm partial to Bavette's for steak.

Weather is a huge x factor, as others have said. Cubs game would be fun if it's decent.

We did a Frank Lloyd Wright walking tour in Oak Park around that time of year. It was chilly, but worth it if you’re into that sort of thing.

FLW Tours

Giordano’s for Deep Dish
Shopping along Michigan Avenue
Steppenwolf Theater (See if the show they’re running interests you)

And agree with everything else ppl have suggested.