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Ah, Blues Fest is my signal to know that summer has arrived in Chicago! It seems to kick off the season of festivals and fun all summer long! At the end of summer the Jazz festival kicks in, and I start feeling sad for the loss of summer.
I don't know where you will be staying, but going to the Blues Fest will have you in the 'new' Millennium Park so you'll see the 'Bean' as you wander around. In Grant Park (adjacent) we have Buckingham Fountain which is spectacular when lighted at night.
You need to spend some time walking down the 'Magnificent Mile', ...Michigan Avenue...especially from the river and points north. There you will see the Tribune Tower and many other architectural beauties. The street is filled with beautiful, artistic and clever plant arrangements in summer as well as many shops, including things like Tiffany's and Gucci as well as some a little more practical.
If you have the time, and weather permits, you might feel like 'beaching' it, and Oak Street beach is the place to be and be seen. The whole lake front has walking and biking paths all along the way. And farther down that way (north) is our Lincoln Park and it's wonderful zoo...perhaps the only free zoo left in the country. There is the Shedd Aquarium, Adler Planetarium, right on the lake near the festival, if things like that interest you. We have a great Science and Industry museum, but that's a little south of the city center.
There are some great architectural tours by boat along the river if you have an interest. The architecture in the Chicago area is fantastic, from Louis Sullivan to Frank Lloyd Wright and in between.
There are cruises out on the lake, jazz brunches and night cruises that give a great view of the city at night, and that also has entertainment. Every ethnic group you have heard of has a restaurant with their specialized cuisine in Chicago.
I am sure you will enjoy Buddy Guy's place, and hopefully someone will surprise the customers with a sneak visit...that happens now and then. I actually saw Buddy with Koko Taylor one time in a small joint south of the city.
I'm sure that I have described more than you would have time for, and also perhaps more than you would be interested in. I know you will have a great time! Enjoy, and welcome to Chicago!!!
Oh, .....and it's "Go White Sox" in my neck of the woods!!!
Thanks for all of the wonderful suggestions. We'll be staying not too far from Grant Park, so I will definitely check out some of the things you suggested. More than likely we'll spend most of the time at the festival. I was originally going to go to a Cubs game on Sunday but that might not happen. That way I'll have time to see more of the city.
Yep festival season is officially here. For us it is the Doheny Blues Festival that kicks things off. That was just this past weekend. In spite of the overcast skies it was excellent as always.