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If I'm not around to show you the town myself.

I can't think of a sensible way to approach hometown in this site, except to imagine someone coming to town when I am out of town myself.  What should they do?
 
A big part of what makes Chicago Chicago is the neighborhoods and the ethnic variety.  Having a meal in Greektown or one in the Italian area along Taylor Street are two of the most accessible ways to experience something that usually takes a car.  Check out recommendations in Chicago Magazine.
 
Everyone I meet from Mexico says that the best Mexican restaurant in the world is in Chicago, Topolo Bombo and its companion, Frontera.
 
One of the few German restaurant survivors is the Berghoff, which is in the Loop.  Some new dishes have been added to the traditional menu, which features favorites such as sauerbraten.
 
Everyone wants to go to a steakhouse, but Chicagoans don't do this much themselves, except when there are guests around.  An old place that Chicago families have gone to for years is Gene and Georgetti's, near the Merchandise Mart.
 
Many visitors want to check out blues clubs.  Again, the most accessible one is Kingston Mine, a short taxi ride away.
 
For museums, the Art Institute, Field Museum (natural history), and Museum of Science and Industry are world class.  You will be best off taking a car the the Museum of Science and Industy, which is on the South Side, near the University of Chicago.  The Aquarium, including the Oceanarium, is a great visit with kids, and is close to the Field Museum.  If you do only one thing in Chicago, see the impressionist collection at the Art Institute.
 
For those interested in architecture, the walking tours given by the Chicago Architectural Foundation and the boat tour up and down the Chicago River are very informative.  Those interested in Frank Lloyd Wright should get in a car and drive to the Frank Lloyd Wright Home and Studio, and then walk or drive around to see the other Wright buildings in Oak Park and River Forest.  They also are scattered around other suburbs, but this is the best concentration.
 
Hidden architectural gems?  Try these.  When security blocks you, just look around the lobby as best you can.
  • For those with a little extra time, visit the public rooms in the Cultural Center, formerly the library.  Michigan between Randolph and Lake.
  • The State of Illinois building is a fascinating modern experiment -- all atrium.  Take a ride up an elevator.
  • 77 West Wacker (corner of West Wacker and North Clark).  The classical lines epitomize the 1990's.  Designed by Catalan architect Bofil.
  • 190 South LaSalle.  Designed by Philip Johnson.  The ostentation of the 1980's.  Yes, that is a gold leaf ceiling in the cavernous lobby -- about one molecule thick!
  • LaSalle Bank Building, 135 South LaSalle.  Enter on Clark or LaSalle and walk through this Art Deco masterpiece.  Old-timers still call it the "Field Building."
  • Marquette Building.  140 South Dearborn.  The lobby is a turn of the century gem.
 
Inside advice?  Many think the views from the Hancock Building are better than the views from Sears Tower.  There is a restaurant near the top, where you can take in a meal and the view, without paying for the observation deckSignature Room at the 95th
875 N. Michigan Ave. (900N, 200E), Chicago
Tel: (312) 787-9596
 
For a drive out of the central city, drive north along Lake Shore Drive until it ends, then follow Sheridan Road north as it bends along the lake.  Try to stay on the main road; try to keep the lake on your right.  You will be in sight of the lake many times, and you should stop at public beaches beginning at the lighthouse in Evanston.  Just before then, you will pass Northwestern University.  Not long after the light house, stop at the Bahai Temple in Wilmette.  You can't miss this landmark "God's orange juice squeezer."  The gardens are among the best in town.  Keep following Sheridan Road through Wilmette, Kenilworth and Winnetka.  If you aren't lost by then, you will go through a series of ravines.  Along the way, you will see some fantastic mansions.  After the ravines, you can declare victory, turn around and go home.  If you have the rest of the day to kill, seek out the Botanic Gardens along Lake Cook Road.
 
Everyone walks up and down Michigan Avenue, the Magnificent Mile, whether I suggest it or not.  It looks great these days, with a lot of plants and trees.
 
There is a private riverwalk with outdoor cafes and shaded benches along the Chicago River.  You can reach it by going down the stairs at the northeast corner of the Michigan Avenue bridge (look for the bridge sculpture labelled "Discoverers."  Walk along the river toward the lake.  Near the end, turn left (heading north), and make your way to the North Pier area.  You will be surprised to find a group of buildings built around a lock.  This used to be a commercial wharf, and is a pleasant, unexpected area, especially if you sit outdoors on the south side of the water and face north.  This is a great hide-out from the frenzy of Navy Pier, which is just a few blocks away.