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Harvey

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I will be going to Chicago with my wife the last week in May.

I have never been to Chicago and will be staying at The Blackstone on South Michigan Ave.

While she is attending a convention, what should I do there?

 
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Looks like the Cubs are in town...go to Wrigley for a game!

Also, Get a pizza at Pizzeria Uno

29 East Ohio Street

Final Suggestion: A piano bar in Chicago called Howl at the Moon (26 West Hubbard Street) that is really fun and rowdy at night. My wife and I had a blast there the last time we visited.

 
Museum of Science and Industry was a good suggestion.

I took my kids to Shed Aquarium, but I'm originally from Florida and am kind of sick of looking at fish.

 
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Definitely try and catch a Cubs game at Wrigley, check out Millennium Park and the Mag Mile(Michigan Ave). There's a good deal of scenery along that walk. Try and hit the Shedd, the Planetarium as well as the Museums if you have time. If you can buy tickets in advance as the lines can be a bit insane.

Jeremy

 
A very nice time to come to Chicago. A short walk east will put you at Buckingham Fountain. A little further and you'll be at the lake. Go north form there and you'll be at Navy Pier or south to the museum campus. You can walk a little north on Michigan Ave to Millennium Park or a little further to the Chicago river and do the site seeing boat ride.

 
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