Stay at a hotel in central Chicago. Consisting of downtown, Lincoln Park, the Magnificent Mile, the Loop, Old Town, River North, Grant Park and the Gold Coast, the central region is well connected with public transportation and houses most of the city's attractions. Staying in the heart of the city will set you up for your exploration.
Get a good city map. All hotels will have a free city maps, so you should use them. Take a few minutes to locate all the things you want to see, and plan out your itinerary. Without a good plan, you could spend a lot of time going from place to place.
Use your feet. Walking and biking are the best ways to see Chicago. The city ranks as the fourth most walkable large city in America, with the Loop, the North Side and Lincoln Park ranking as the top neighborhoods, according to Walk Score. Chicago is also a very bike-friendly city. "The city has bike lanes, valet bike parking, indoor bike racks and more," according to Bicycling.com. Bobby's Bike Hike, located near Navy Pier, lets visitors see the city on two wheels. The tours provide bike rentals, safety equipment and guides.
See the city at night. Navy Pier, Millennium Park and the entire skyline are brilliant once the sun sets. Head to the lakefront to catch the shimmering reflection on Lake Michigan's dark waters. Walk along the waterfront to Navy Pier for fireworks (every Saturday and Sunday), entertainment, food and drink.
Head to the Signature Room's lounge at the John Hancock Observatory before sunset. The Signature Lounge, perched on the 96th floor, is less of a tourist attraction, unlike the Willis Tower Skydeck, and more of a local institution. Providing dramatic views of downtown, the lounge serves drinks, appetizers, sandwiches and desserts. The lounge offers a better view and a more relaxed ambiance than Willis Tower.
Take in a ballgame. You can choose between the North Side's lovable losers or the South Side's blue-collar ballplayers. Wrigley Field, the Chicago Cubs' ballpark, is sacred ground to baseball fans with its manual scoreboard and ivy-covered brick walls. U.S. Cellular Field, the White Sox field, is located in Armour Square. From April till September, and possibly into October, watching Chicago's boys of summer is a great way to experience one of America's great sports cities
