DAY 1
There's no need to rent a car in Chicago. From the airport, you can easily reach Chicago's downtown by shuttle, taxi or public transport. And after checking in at your hotel, the first order of business is to discover the delights of the Magnificent Mile, one of the world's glitziest shopping boulevards.
You'll want to visit the multi-storied shopping malls like Water Tower Place, 900 North Michigan, Chicago Place and The Shops at North Bridge. But don't neglect the trendy boutiques on fashionable Oak Street, Niketown or that Valhalla for little girls, American Girl Place.
When it's time to think about dinner, you'll have hundreds of restaurants to choose from. Try one of the stylish restaurants along West Randolph Street, a former market district in the West Loop Gate neighborhood that has become the city's favorite new hotspot for dining and nightlife.
If your motor is still running after that, stop in for a nightcap at one of the city's nightclubs or friendly bars.
DAY 2
Start with coffee. Then take a Chicago Trolley Company or Chicago Gray Line tour to introduce yourself to the city. A little culture? Visit the Museum of Contemporary Art whose collections focus on works created since 1945. If you're more of a traditionalist, view the great masters at The Art Institute of Chicago. Of more than 300,000 works, the impressionist and post-impressionist paintings are considered among the best in the world.
After lunch - seafood at McCormick & Schmick's or Mity Nice Grill, perhaps - you'll love exploring a working coalmine or clambering through a German U-boat at the Museum of Science and Industry.
Alternatively, visit the Museum Campus which includes The Shedd Aquarium, the Adler Planetarium, and The Field Museum, home of Sue the largest, most complete Tyrannosaurus Rex ever discovered.
Later, take in spectacular views from The Hancock Observatory or the Sears Tower Skydeck. The Sears Tower is higher, but the Hancock is closer to the Lake. Hmm! Tough choice.
Now it's about time for gourmet dining again. How about a succulent steak at Gibson's, The Saloon, or Ruth's Chris Steakhouse? Or the exotic cuisine of French Indo China at Le Colonial?
End the evening at one of Chicago's famous jazz clubs like The Green Mill or Andy's Jazz Club. Or combine good jazz and fine dining at the Green Dolphin Street.
DAY 3
A hearty breakfast at Lou Mitchell's where the original Route 66 began, then it's off on a Chicago Neighborhood Tour to explore one of the communities such as Wicker Park or Chinatown. Or perhaps a visit to Navy Pier where, among the hustle and bustle of shops and restaurants, you'll come upon one of Chicago's lesser-known jewels - the Smith Museum of Stained Glass.
After lunch, visit the Chicago Cultural Center where you can take a self-guided tour and marvel at its beautiful Tiffany Dome, as well as the thought-provoking, free art exhibits. Then visit Chicago's landmark department stores, Macy's on State Street, "that great street."
Later, try one of Chicago's favorite deep-dish pizzas at Giordano's or the original Gino's East. Sample world-class theater at The Goodman Theatre or Steppenwolf Theatre; enjoy a Broadway-style show at the Cadillac Palace Theatre or Ford Center for the Performing Arts/Oriental Theatre, or improv at The Second City or ComedySportz. Or sample the energetic and wildly popular Blue Man Group.
If you'd prefer music, end your visit with an appropriate flourish with some Chicago Blues at Blue Chicago or Buddy Guy's Legends. All this and you only scraped the surface. Make a note to come back again soon!