As the third largest city in the United States and one of its leading transportation hubs, Chicago has long served as the crossroads of America. It is the place where everyone from farmers to mobsters, musicians to financiers, and athletes to actors have gathered to stake their claim to the American dream. It is a city rife with history and remains of the country’s main cultural and intellectual centers. 

Take a look at the guide below and post your thoughts and suggestions as well.

Willis (Sears) Tower

233 South Wacker Drive

At the time of its completion in 1973, this iconic Chicago landmark was the world’s tallest building, surpassing the World Trade Center in New York. Today, you can still go up to the 103rd floor Skydeck and see all the way to Indiana.
www.theskydeck.com

The Field Museum

1400 South Lake Shore Drive

Discover Sue, the world's largest and most complete Tyrannosaurus Rex. Or descend into an Egyptian tomb and see 23 Egyptian mummies and 5,000-year-old hieroglyphics. Whether you’re with the kids or touring alone, this natural history museum is one of the city’s must-sees.
http://fieldmuseum.org

Grant Park

Between Michigan Avenue and Lake Michigan

Often called “Chicago’s Front Yard,” Grant Park is a large open-space park with walkways, gardens, performance venues, and sporting and harbor facilities. It is bordered on the north by Randolph Street, on the south by McFetridge Drive, on the west by Michigan Avenue, and on the east by Lake Michigan. If the weather is mild, the park is great for a mid-afternoon or early evening stroll.

Wrigley Field

1060 West Addison

The Cubs won’t be playing, but it's still worth a stop at one of baseball’s most famous addresses, where you can take tours of the ballpark starting in March. Tours can include visits to the seating bowl, press box, bleachers, visitor's clubhouse, Cubs' clubhouse, and Cubs' dugout, as well as a chance to step on the field.
http://chicago.cubs.mlb.com/chc/ballpark/tours/index.jsp?content=daily

Navy Pier

600 East Grand Avenue

A 3,300 foot pier extending into Lake Michigan, the Navy Pier is Chicago’s number one tourist destination. Originally built for commercial and entertainment purposes, today it is center for shops, restaurants, and amusement park rides and entertainment. Make sure to ride the famed 260-foot Ferris wheel, if weather permits.
www.navypier.com

The Magnificent Mile

Michigan Avenue between the Chicago River and Oak Street

Feel like shopping? Explore more than 460 exclusive stores and 200 restaurants in this one-mile stretch of Michigan Avenue (between the Chicago River and Oak Street). In addition, you can see numerous prestigious buildings located along the Magnificent Mile, such as the Wrigley Building and the John Hancock Center.
www.themagnificentmile.com

Willie Dixon’s Blues Heaven

2120 South Michigan Avenue
1-312-808-1286

Former home of Chess Records, the famed blues label, this building housed a studio and recording company that begat legendary recordings by Muddy Waters, Chuck Berry, Howlin’ Wolf, Bo Diddley, John Lee Hooker, Etta James, Koko Taylor, Buddy Guy, and Aretha Franklin. For a small donation, you can still take a quick tour of the office and studio and see memorabilia from the greats.
www.bluesheaven.com/tours/

Biograph Theater

2433 North Lincoln Avenue

You can see a live show at the theater these days but that’s probably not the reason most tourists come to this small theater in the Lincoln Park area of Chicago. It was here where bank robber John Dillinger was shot by FBI agents after watching a gangster movie on July 22, 1934. For more Chicago gangster landmarks, you can take a gangster tour to see famed landmarks such as the Holy Name Cathedral, where gunmen hired by Al Capone famously killed Earl "Hymie" Weiss in a hail of gunfire, leaving a bullet wedged into the cornerstone.

Second City

1616 North Wells Street
Tickets/Box Office: 1-312-337-3992

The famed theater group/comedy club that spawned the likes of John Belushi, Bill Murray, Tina Fey, Steve Carell, Stephen Colbert, Second City continues its role as a key breeding ground for the nation’s comedic and improvisational talent. Shows nightly.
www.secondcity.com

Millennium Park

201 East Randolph Street, between Michigan and Columbus Avenues
1-312-742-1168

Hosting more than 525 free events each year, Millennium Park is an award-winning center for art, music, architecture, and landscape design. Weather permitting, you can take an afternoon or evening to stroll through the 24.5-acre park, which features the work of world-renowned architects, planners, artists, and designers.
http://explorechicago.org/city/en/millennium.html

The Art Institute of Chicago

111 South Michigan Avenue

During ASCD's Annual Conference in Chicago, the Art Institute will be hosting a major exhibition celebrating the work of artist Pablo Picasso. More than 250 of the Art Institute’s collection of Picasso’s paintings will be on display, including sculpture, prints, and drawings as well as major loans from private collections in the city.
www.artic.edu/aic/