Have a great time--Chicago_s a fun city.
Take him to Tommy Guns Garage for dinner and a show. It is a wild night! You have to give a password at the door :) and then you have a great dinner and an interactive (there is audience participation!) show about gangsters and prohibition and runnin_ booze in Chicago in the _20s. It is a hoot!
You could really pull one over on your hubby - he_ll get a kick out of you _knowing_ the password at the door!
http://www.tommygunsgarage.com/
It is Chicago_s longest running audience interactive dinner theater show - most obviously because it is GREAT!
http://www.fogodechao.com/),
a meat lovers restaurant. You pay one price and are served about seven different kinds of meat by waiters dressed as gauchos who bring it to your table on skewers and slice it right there. Beef ancho, fillet mignon, pichana, alcatra (top sirloin), fraldinha (bottom sirloin), cordeiro (lamb), frango (chicken drumsticks and chicken breasts wrapped in bacon), etc. They give you a card and when you_re ready for something new, you flip the card the green side and when you want to take a break, you flip it to the red side. It_s a unique dining experience.
As far as a show, try Zanies comedy club (
http://www.chicago.zanies.com/).
It_s the top stand up comedy place in town. There are different acts almost each night, but I_ve had a good time every time I_ve gone. And they say that laughter is a great aphrodisiac :)
You might also want to check out the Green Mill Jazz lounge (
http://www.greenmilljazz.com/).
Even if you_re not a big fan of jazz, you_ll love the atmosphere. The place used to be the hangout of Al Capone and still retains some of that aura. There are dark booths, waiters in ties and aprons and great music almost every night of the week (except Sunday when they hold the weekly Poetry Slam, which is also a great time). Dress up a little (you don_t have to, though) and pretend you_re both members of the Rat Pack waiting for Frank or Sammy to show up. I was there one time and to my left Ani DiFrank (an indie music star who had a concert nearby) and former SNL star Nora Dunn, and on my right was Jeremy Piven and John Cusak. It was weird. But be warned: lines have been known to form to get it. The place isn_t that big, so you may want to get there earlier in the evening.
Personally he might like a good steak dinner at one of the many steak houses just north of the Loop area. From Ruth Chris_s to Mortons (which is more local) there might be a steakhouse just for him.
Theaterwise....if you can find tickets, Blue Man Group might be one of the most unique shows you will ever see....caution though as tickets sell out way in advance. If you want a taste of Broadway, the Broadway in Chicago shows are cool to see as well. Currently Wicked is continuing its long run at the Ford Center for the Performing Arts....also The Color Purple which is based on Oprah Winfrey_s bestseller is playing.
But if Broadway is not your thing, there are many smaller more intimate theaters. As was mentioned in a previous answer, Second City which is in Old Town is an excellent choice. All around the city there are other more local theaters you can check out as well.
Have fun...Chicago is a great place to go in the summertime!!
http://www.gejascafe.com/
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