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Located on the eastern edge of the beautiful Washington Park, this museum is named after Chicago’s first non-native settler, Jean Baptiste Point du Sable. The permanent exhibits here celebrate other firsts, such as the first black US astronaut, Major Robert Lawrence, and Chicago’s first and only African-American mayor, Harold Washington. Thought-provoking exhibits include rusted slave shackles and the “Freedom Now” mural, depicting 400 years of African-American history from the early days of slavery to Civil Rights marches.

Chicago’s elevated trains (the El) provide an inexpensive roofline tour of the city. The Brown Line in particular warrants riding en famille from Chicago Station south over the Chicago River and around the Loop, threading between the massive buildings of the financial district. Sit in the first row of the front car for an exciting view of the city ahead of you (see The El).

The Benevolent and Protective Order of Elks, an American fraternity (founded in 1868 and still going strong), built this magnificent structure in 1926 to honor its World War I veterans. It’s since been re-dedicated to pay homage to World War II, Korean and Vietnam war veterans. Two larger-than-life elk statues flank the wide entrance steps, while inside, every inch is richly decorated. The 100-ft (30-m) marble rotunda, murals depicting the Sermon on the Mount, intricate windows, and allegorical bronze sculptures are awe-inspiring.

The impressive 13-story Sky Lobby offers a great place to unwind, with its soaring atrium. Glass-sided elevators whisk guests to suites with amenities that include high-speed Internet access and microwaves. Full American breakfast is also included.

This hotel’s seven-story garden atrium makes a pleasant retreat from the hustle and bustle of the nearby convention center and airport. Suites have all the necessary facilities; cooked breakfasts and an airport shuttle are complimentary.

In Chicago there’s a theater company for every demographic and Emerald City is its troupe devoted to young audiences. Expect lively productions such as Where the Wild Things Are as well as holiday season shows in weekend-only midday matinees at Lincoln Park’s Apollo Theater.

Born in Oak Park, this hard-living author (1899–1947) left the suburb of “wide lawns and narrow minds” at age 19.

Chef Erwin Drechsler offers up a “melting-pot” cuisine, complemented by a superb wine list. Sunday brunch is a real treat.