Chicago's name derives from a Native American word meaning wild garlic or "place of the skunk". There's nothing of the skunk about Barack Obama's home city. Within a day's drive of more than half the country, Chicago, with its bold architecture and rich cultural and sporting life, just feels right, due in no small way to the city's green arc known as the "emerald necklace". It's a fine example of visionary urban planning, yielding a people-friendly 42-kilometre swathe of city parks, tree-lined boulevards and grassy squares.
Frank Lloyd Wright's Oak Park (www.flwright.org/) is a picturesque, historic neighbourhood easily reached by train. Wright developed a new American architecture – the Prairie style – in his Oak Park studio. Take a self-guided tour with audio guide to view the world's highest concentration of Wright-designed structures. Lincoln Park is a green, hip neighbourhood, home to the acclaimed Steppenwolf Theatre (www.steppenwolf.org/) – think August: Osage County – and The Second City (www.secondcity.com/), for terrific improvisational comedy. Alumni include Tina Fey, Alan Alda and Bill Murray.
As well as deep-dish pizza, try The Art of Pizza (www.artofpizzainc.com/) – Chicago loves a prime steak. In River North, within easy walking distance of central Chicago, is Bavette's Bar and Boeuf (www.bavetteschicago.com/food/). This sophisticated French-influenced, jazz-era steakhouse serves exceptional quality food and lethal cocktails. Nearby Kinzie Chop House (kinziechophouse.com/) is also meat central, while RPM Steak (www.rpmrestaurants.com/rpmsteak/chicago/) is where President Obama recently enjoyed a "Kansas City" cut with baked potato and Grey Goose martini. 42 Grams (www.42gramschicago.com/) received two Michelin stars in its first 10 months. It's pricey ($US243 [$342] with no alcohol) but the 15-course tasting menu is a work of art.
The Art Institute of Chicago (www.artic.edu/) in Grant Park is considered one of the world's finest galleries. Its extraordinary modern art collection includes nearly 1000 works from Europe and the Americas and includes Matisse's Bathers by a River, Picasso's Old Guitarist and Wood's American Gothic. Numerous restaurants/cafes allow visitors to collapse and revive. Buy tickets online to bypass queues, from $US29.
Chicago's architecture reflects America's architectural history. The Chicago Architecture Foundation (www.architecture.org/) runs excellent river cruises (as well as walking, bus, bike, trolley and "El"-train tours). Docents (who ask not to be tipped – remarkable!) know everything there is to know about Chicago's past. Book at Ticketmaster (www.ticketmaster.com.au). Cruises resume in April.
The city has its share of flashy hotels, like the Waldorf Astoria (www.waldorfastoria3.hilton.com/), the Peninsula (www.chicago.peninsula.com/) and the Thompson (www.thompsonhotels.com/) but for a touch of America's retro golden era, the Hotel Allegro (www.allegrochicago.com/) is a little art deco beauty centrally located in the downtown theatre district, within the Loop and walking distance from Union Station. Meet other guests at the evening hosted wine receptions. Try for an upper room to avoid traffic noise.
Three suggestions: Hire a bike ($US30 per half-day) from Bike Chicago at Millennium Park (www.bikechicago.com/) and cycle the Lake Illinois 29-kilometre trail. Gawk at the Beaux Arts-style Great Hall at Union Station (www.chicagounionstation.com/). Visit the Friendly Confines of historic Wrigley Field (www.chicago.cubs.mlb.com) to experience the camaraderie and family atmosphere of a Major League Baseball Chicago Cubs game.