Chicago, IL:

            The windy city if my favorite city in the U.S., I love Chicago with or without the freaking freezing winters!  It might not be as flashy as a New York or LA but it has a lot to offer.  Lincoln Park Zoo is the best zoo EVER (free) and is located right off Lake Shore Drive!  Downtown is the best!  Whether you are walking along Michigan Avenue checking out the city (Magnificent Mile) or shopping on State Street there is always something to see or do.  If you want to spend the day walking around head down to Grant Park to watch some 16" softball (real softball), hit Shedd's Aquarium (one of the best),  check out the Planetarium or the Field Museum or go to the awesome Art Institute of Chicago.  Make sure you hit the Mercantile building to watch some traders, Sear's Tower for a great view, Navy Pier (ride the ferris wheel) and the Hancock building for a drink on the 96th floor.  Welcome to sport's land (though not so good these days;-), an afternoon at Cominsky or Solider Field is great but nothing beats the ivory covered walls of Wrigley (Red line on the El from the city)!  There are a ton of bars and restaurants up in Wrigleyville so if you hit a game take your time up there.  Sports Corner, Murphy's and the Cubby Bear are a ground ball away from the park and two of my favorites.  Cab it back or stay on the El, plenty more places to dine and drink at on Halsted, Lincoln and Division.  You can't do wrong with drinks at Mother's, Cavanaugh's, Lucky Strikes and John Barleycorn's.  Some Blues at Lily's and Blue Chicago are awesome!  Cocktails at Tavern on the Green and dinner at Vong's is nice for a date night.  Chicago has some super places to stay and the Hyatt Regency or Fairmont off Wacker (by the Chicago River) are two of my favorites.  For a stay in a more vintage and famous place you can try the Drake or Inter-Continental (great pool).  Enjoy your stay but before you leave have some Chicago's pizza (773-477-2777), the BEST!
 

        St. Louis, MO:

            St. Louis is a fun town.  Even though it is relatively small there are a ton of things to do.  Forest Park and the zoo are great places to visit on an sunny afternoon.  The Galleria in Clayton is great for shopping.  Anheuser-Busch Brewery is a nice tour.  Downtown is a lot of fun with the bars and restaurants in Union Square (refinished train station) and Laclede's Landing.  St. Louis has also has a great river front with its paddle boats (casinos) and the Arch, a ride to the top is an experience (tight but interesting).  The Hill (area in south St. Louis) is a great place for Italian food.  Some good places to grab a beer are Dressel's, Seamus McDaniel and Senior Frogs.  Central West End (CWE) is a great neighborhood to walk around and live (one of the stops off the MetroLink, a great pubic transit system).  There are a ton of stores, pubs and restaurants in CWE and it is close to the Park.  Two of my favorite bars are in CWE, the Pub Above and Tom's Bar and Grill.  A couple great places to stay while in town are the Adam's Mark, Hyatt Regency at Union Square and the Millennium Hotel (revolving restaurant).  If you get a chance try and catch a game at Busch Memorial Stadium.  While it is no Napa, a trip up to St. Charles is very pretty.  Right on the river St. Charles is a great town with a few small wineries, a bunch of shops and some great garden restaurants to hang out at and enjoy the moment.
 

        Iowa City, IA:

            Iowa City is a great college town, whether you are hanging out on the steps of the Old Capital building (use to be the Capital of Iowa) or drinking at Joe's.  The Sheraton downtown is a good place to stay, as you are close to the action.  The pedestrian mall is great to people watch (designed by the same guy who did the Pearl Street mall in Boulder).  Some great places to hang out are the Vine, Fitzpatrick's, the Deadwood and Mickey's.  Make sure you grab a George's gyros when closing down the bars! A must see is Pints on Dubuque street, if you go say hi to Shaggie aka Doug!
 

        Ann Arbor, MI:

            The greatest place to watch a football game!  No place better than sitting in Michigan Stadium with 100,000 plus other people and rooting on the Maize and Blue!  Hail to the Victors!!!!!!!!!!!!!!!!