No big city embraces summer more than Chicago. Sunbathers jockey for space on the sandy shores of Lake Michigan. Millennium Park booms with free concerts and spurting fountains, and streets teem with food, music, and ethnic festivals (for a schedule, go to explorechicago.org).
While adults can take in art museums and architectural history, kids can revel in a children’s museum and an aquarium. Personal experience and locals’ tips helped us cull the best of Barack Obama’s pre-presidential stomping grounds.
Explore Chicago’s patchwork of unique neighborhoods on foot or the L train, the city’s public-transportation rail network. Especially fun are the Bucktown, Wicker Park, and Lincoln Park communities—all with lots of independent cafes and boutiques. Just east of Lincoln Park is a stretch of the city’s walkable 26-mile lakefront.
Anchoring the city’s lively arts scene is the Art Institute of Chicago (111 S. Michigan Ave.; 312-443-3600; artic.edu) and its new Modern Wing, a decade-long project that makes the art museum the second-largest in the country. The new wing holds 20th- and 21st-century works, from European paintings to photography. Like outdoor art? The 25-acre Millennium Park (millenniumpark.org) holds a Frank Gehry–designed concert pavilion, a 50-foot rectangular fountain, and the reflective, bean-shaped “Cloud Gate” sculpture by Anish Kapoor.
In Chicago, culture also takes the form of comedy. Check out a show by Second City (secondcity.com), a 50-year-old troupe that has nurtured such jokesters as Tina Fey, Steve Carell, and Stephen Colbert.
Families can visit 232,500 marine animals at the Shedd Aquarium (1200 S. Lake Shore Dr.; 312-939-2438; sheddaquarium.org) or go to the Chicago Children’s Museum (700 E. Grand Ave.; 312-527-1000; chicagochildrensmuseum.org), where kids can design skyscrapers, simulate a dinosaur excavation, and climb a three-story schooner.
While boat trips are often tourist traps, architecture tours from the Chicago River give an unrivaled look at the Windy City’s significant contribution to building design. One of the best companies is Wendella (312-337-1446; wendellaboats.com), whose 75-minute outings are an informative and fun crash course in architecture’s most important names, styles, and dates.
Less than a year old, the Elysian (11 E. Walton St.; 312-646-1300; elysianhotels.com; rates from $395) is already considered Chicago’s most luxurious hotel. Why? For starters, Carrara-marble bathrooms, rooms that average 890 square feet, and access to luxury cars.
Architecture buffs might prefer the boutique Hotel Burnham (1 W. Washington St.; 312-782-1111; burnhamhotel.com; from $199 in summer), a steel-and-glass building from 1895 that inspired the Chicago skyscrapers that followed. Some original touches remain, including terrazzo-tile floors and marble wainscoting.
If it’s high-rise views you’re after, check into the Dana Hotel and Spa (660 N. State St.; 888-301-3262; danahotelandspa.com; from $189), where most rooms have floor-to-ceiling windows, and there’s a bar on the roof.
Chicago’s food scene has so much depth and variety that the culinary magazine Saveur devoted its October 2007 issue to the city. Articles waxed poetic about Mexican and Polish cuisine, a proliferation of small-batch beer breweries, and even Southern soul food.
Restaurants range from Big Star (1531 N. Damen Ave.; 773-235-4039; bigstarchicago.com)—a new cash-only taco joint from chef Paul Kahan—to the hyper-modern Alinea (1723 N. Halsted St.; 312-867-0110; alinea-restaurant.com), recently ranked one of the world’s 50 best restaurants. In between are scores of good, affordable neighborhood spots; some of our favorites include the $8 grass-fed-beef burgers at DMK Burger Bar (2954 N. Sheffield Ave.; 773-360-8686; dmkburgerbar.com), the constantly changing wall-size Modern American menu at Chalkboard (4343 N. Lincoln Ave.; 773-477-7144; chalkboardrestaurant.com), and the new and charming Kith & Kin (1119 W. Webster Ave.; 773-472-7070; kithandkinchicago.com) near DePaul University; the food is both hangover-friendly (fried chicken) and sophisticated (salmon crudo with lentils).