DAY 1
Summer in Chicago means a visit to Navy Pier - Chicago's favorite summertime spot for recreation, entertainment and outdoor fun. Enjoy a ride on a speedboat, motorboat or sailboat, or enjoy a meal on one of the boats that offers lunch and dinner daily the Seadog, the Spirit of Chicago, the Odyssey and Mystic Blue Cruises.
Later, get an eagle's eye view of the Chicago skyline from the seat of one of Chicago's most famous inventions the giant Ferris Wheel. Wander down Dock Street and enjoy the roving entertainment.
Later, visit the North or South Side of Chicago to enjoy a night baseball game at Wrigley Field (Chicago Cubs) or U.S. Cellular Field (Chicago White Sox) - don't forget to try a Chicago hot dog!
DAY 2
Spend the day at the Museum Campus and purchase a CityPass to enjoy the Adler Planetarium, Field Museum and Shedd Aquarium. Use it later at other locations, including The Hancock Observatory and the Museum of Science and Industry - an unmatched adventure of inventions and ideas situated in Hyde Park, home to the University of Chicago.
Time for lunch? Enjoy La Petite Folie, a delightful Hyde Park French bistro. Afterwards, come back downtown for a walk through Grant Park to marvel at Buckingham Fountain, a Chicago landmark since 1927.
In the evening, enjoy one of the many free music concerts taking place in the park during the summer festival season such as the Grant Park Music Festival. If it's a Tuesday in the summer, take a blanket and picnic under the stars while watching a classic film at the free Outdoor Film Festival.
DAY 3
Begin the day with a jog or a swim at Oak Street Beach - a perfect stretch of white sand and blue Lake Michigan water right in the middle of the city where sand castles are built alongside skyscrapers. Stop at the Lincoln Park Zoo - one of the only free zoos in the world - then visit the unique The Notebaert Nature Museum.
Later, wander back to the hotel through Old Town and perhaps discover one of the many film shoots in action that add excitement to Chicago each year. You might also stumble upon an arts and crafts festival showcasing artists from all over the country displaying their creations for sale.
For dinner that evening, enjoy some world class Chicago-style spare ribs at Carson's Ribs or Twin Anchors! If ribs aren't your style, try one of those relaxing dinner cruises on Lake Michigan or a fun meal at the family-favorite, Hard Rock Café.
DAY 4
Depart from the hotel in a rental car - drive to a Chicago favorite, Eli's Cheesecake World, and learn how one of America's favorite desserts is made at this state-of-the-art facility - even decorate your own slice of cheesecake!
After driving back downtown, the next adventure begins with a drive along Route 66 in Illinois, which originates in Chicago, at the corner of Columbus Drive and Jackson Street.