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Highlights Tour
Home » Chicago » Chicago: 1-2 Day Itineraries » Highlights TourIf this is your first visit Chicago, this may be the itinerary for you. This itinerary can also be good for families, since it has something for everyone.
Day One: Spend the morning at the Art Institute. This is a world-class collection with masterpieces from every culture and period of art history. Especially famous works include Seurat’s A Sunday Afternoon on La Grand Jatte, van Gogh's Bedroom at Arles, and Monet's Stacked Wheat -- the Impressionist collection is generally regarded as the best outside of France. Georgia O'Keeffe's Black Cross, New Mexico Ayala Altarpiece, Caillebotte’s Paris Rainy Day, Hopper's Nighthawks, and Grant Wood's iconic American Gothic are also at the Art Institute. Do allow yourself time to discover some of the cultural treasures a little off the beaten path, such as those in the many collections of Asian and African art, the European decorative arts, and 20th-century painting and sculpture. Since it is a very large museum, you may want to chart your course through the collections ahead of time so that you can see what you want to see before your feet start hurting.
The Art Institute has its own restaurant, which serves delicious contemporary American food. Sopraffina (closed weekends) or Zoom Kitchen would also be good choices for lunch near the Art Institute (see associated article on activities and restaurants). After lunch, head to the Museum Campus, south of the Loop on Lake Michigan, and visit either the Field Museum of Natural History or the Shedd Aquarium. By 5:00, when both usually close, start making your way through Grant Park back to the Loop. If it's nice out, enjoy the views of Buckingham Fountain or even go up to the Wildflower Works (north of the Art Institute). Finish your eventful day with a delicious, hearty dish of sauerbraten or goulash at the Berghoff, Chicago's oldest restaurant.
Day Two: Get up early and make it to the Sears Tower before the crowds... at least before some of the crowds. It opens at 9:00 AM. Enjoy your incredible view of downtown Chicago; if it's a clear day, you may even be able to see as far as Indiana, Michigan and Wisconsin!
Once you've got your feet planted back on the ground, give yourself some time to wander northeast through the Loop and across the Chicago River, taking in the street-level views of some of the buildings and outdoor sculptures you saw “aerially” from the Sears Tower's observation deck. The beautiful Rookery, the Chicago Board of Trade, Mies van der Rohe’s Chicago Federal Center and Alexander Calder's “Flamingo” sculpture are all within a few blocks of the Sears Tower.
Have lunch at Gold Coast Dogs, one of Chicago's famous hotdog outlets in the Loop. Or, if you'd rather hold out for some delicious Italian deli fare, wait and eat at L’Appetito in the John Hancock Center -- either one is a perfect lunch at a perfect price. One way or another, make your way across the Chicago River and up the Magnificent Mile. Here, you'll have opportunities galore for both people-watching and window-shopping. Near the Water Tower, stop at Hot Tix, where you can get half-priced theater tickets for that night (or for the rest of the weekend, if it's Friday). After a dip in the hotel pool, head back out for dinner and the theater. Go to sleep dreaming of towers and sculptures, dresses and desserts... you've just finished a whirlwind tour of the Windy City!
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