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Chicago

My sister’s father in law was the guy who started the beer cup snake years ago. ESPN did a package on it a few weeks back.
Saw that after going to a DC Defenders game
 
Get a beer at the Old Town Ale House, if you're in the area.
Lovely artwork.

EDIT: just noticed the part about your 11- and 14-year-olds. Do not go to the Old Town Ale House.
 
I live in Chicago. My thoughts and recommendations:
  • The architecture boat tour is awesome and a must.
  • Yes, sit on the third base side of Wrigley to avoid the sun beating down on you. The Bleachers are very fun, but you're in the sun and it's a drunken frat party, so not kid-friendly. Big Star (Mexican) and Smoke Daddy (BBQ) are two good restaurants right next to Wrigley if you want to eat before or after.
  • The Art Institute is world-class but not sure an 11 and 14-year old would enjoy. The Museum of Science & Industry is great and more likely to please your kids.
  • Don't do the Willis Tower. It's a tourist trap that takes over an hour to get to the Skydeck (i.e., the top w/ the glass platforms that extend out and you walk on). You just go from one line on one floor to another for an hour+. The John Hancock Tower's 360 Observation Deck is much better.
  • Like VT said, the West Loop has great restaurants.
  • Cindy's at the top of the Chicago Athletic Association has an awesome view of Millennium Park.
  • Lincoln Park Zoo is very meh. I find it depressing like most zoos.
  • Rent bikes and ride up and down the path along the lake. Can't go wrong north or south. Maybe bring your swim suits and hit up a beach. Chicago's a beach town during the summer.
We were in Chicago this past weekend.

Attended the Cubbies walk off win on Sunday. Pregame at Murphy’s is a must. 3rd base side for seating is the way to go. Was fortunate to get a hookup for 6th row seats between home and 3rd. Only annoying thing about a win is that obnoxious “Go Cubs Go” song they play after the game. Right, @Chipper, Cuseguy and SU Barney?

We ate well. Gibson’s, Crosby’s and Armitage Ale House.

Avoid the 360 thing at the Hancock Building. 50 bucks a head.

Architectural Boat Tour is a must.

Just arrived in Napa. The Summer of Bill Orange marches on.
 
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