This itinerary combines some of Chicago's premier attractions with outdoor activities and warm-weather escapes. It's perfect for families who love fitness and nature, or couples who couldn't decide whether to spend their vacation in the city or at the lake. And daily highs in Chicago in April and September are normally above 50, so consider parts of this itinerary for a trip in early fall or late spring, as well.
Day One: Spend the morning at Lincoln Park, visiting the zoo, conservatory, and Peggy Notebaert Nature Museum. Then whistle "Take me out to the ballgame" on your way to Wrigley Field, about a mile from the Lincoln Park Zoo, for an afternoon Cubs game. Go Cubs!
Day Two: Take an early morning Architectural Foundation Tour (www.architecture.org ), by foot, bicycle or boat. This is definitely one of the best ways to see Chicago, and you may enjoy it so much that you want to schedule a second tour for later in the week; there are dozens of tours that focus on different parts of town and different architects. In the afternoon, walk up the Magnificent Mile, have dinner, and ascend the John Hancock building -- either to the 96th-floor Signature Lounge or the 94th-floor open-air, screened observatory deck. Watch the sun set over the city.
Day Three: Play tennis in Grant Park in the morning, and then cool off and spend the afternoon in the Art Institute. There is also a family golf center north of Grant Park. Spend the evening on Navy Pier.
Day Four: Reserve the fourth day of your trip for a day trip away from the city. Go kayaking or canoeing on the North Fork of the Chicago River (rent a boat at Chicagoland Canoe Base, 773-777-1489). Alternatively, drive out to the Indiana Dunes (or take the train from the Randolph Street Station on the South Shore Line). Here you'll find beautiful beaches on the shores of Lake Michigan, and sand dunes as tall as 100 feet. The Indiana Dunes National Lakeshore and the Indiana Dunes State Park are both local favorites.
Day Five: After your escape into nature, reimmerse yourself in culture by wandering the Loop, checking out outdoor sculptures and beautiful indoor spots such as the Rookery, the Chicago Board of Trade, and the Palmer House Hilton lobby (also see Greatest Hits tour day seven). Investigate play tickets at Hot Tix in the Loop, near the Washington El station. Or, if your day five falls on the first Friday of the month, spend the evening at Adler Planetarium, instead of at the theater. There you can view the stars at the Doane Observatory, and also check out the StarRider shows and the Sky Theater.
Day Six: Walk south through Grant Park to the Museum Campus, and visit the Shedd Aquarium and the Field Museum. Enjoy a picnic dinner at the 12th Street Beach.
Day Seven: Finish the Summer in the City Tour strong, spending the day on the University of Chicago campus, with visits to the Museum of Science and Industry (in Jackson Park), the Robie House, and the DuSable Museum of African-American History (in Washington Park). Browse in some of the many bookstores around campus, and wolf down a thin-crust pizza like you haven't done since college, at Medici on 57th Street.
Resources:
Baty, Chris. Lonely Planet City Guide to Chicago, third edition. Oakland, California: Lonely Planet, 2004.
Given, Tom. Chicago -- Condensed. Oakland, California: Lonely Planet, 2001.