Chicago

Flights And Sights

Flying To Chicago With American Airlines

See the Windy City with an American Airlines flight to Chicago. Crane your neck at prime examples of the modern skyscraper, shop in style on Michigan Avenue and take in selections from the 250,000 works of art at the Art Institute of Chicago when you fly to Chicago with American Airlines.

Tour the architecture of the Loop, an encyclopedia of modern styles.

See the groundbreaking steel and glass of the 1890 Reliance Building, the mixed materials of the elegant Rookery and, of course, the industrial black of the Willis Tower (a.k.a the Sears Tower), the tallest building in the U.S. – which you can ascend for views from the Skydeck on the 103rd floor.

Check out the masterworks of the Art Institute of Chicago

Seek out Seurat's painstaking A Sunday on the Island of La Grand Jatte – 1884, Hopper's iconic, lonely Nighthawks, and the immediately recognizable American Gothic, by Grant Wood. Afterward, stroll into Millennium Park to see your distorted reflection in the Cloud Gate sculpture.

Take the family to Lincoln Park

Lincoln Park has a world-class zoo full of outdoor habitats for zebras, alpacas and Amazonian turtles—admission is free. Make time, too, for the nearby botanical garden called the Lincoln Park Conservatory and activity-filled waterfront. Finally, venture to Lincoln Park neighborhood, where the Wiener's Circle is a brash place to taste your first Chicago-style hot dog.

Catch a day game at Wrigley Field

Wrigley Field dates to 1914 and is the second-oldest Major League Baseball stadium. The ivy-covered walls help give the place its "Friendly Confines" nickname, though the way the bleacher bums—diehard Cubs fans—throw back any home runs hit by the opposition might give you a different impression.

Shop the Magnificent Mile

For designer names and upscale shops, the upper part of Michigan Avenue is the place. Many spots are tucked into soaring malls like Water Tower Place, which themselves are interspersed with monumental skyscrapers – note the terracotta Wrigley Building and Gothic Tribune Tower. Finish off with a classic cocktail at the Drake Hotel's 80-year-old bar, Coq d'Or.

More Things to Do in Chicago

Travel off the beaten path with American Airlines to find more things to do in Chicago. Explore several of master architect Frank Lloyd Wright's visionary houses, see a German U-boat at the Museum of Science and Industry, and sample great food and entertainment options all over town.

See the South Side for Hyde Park

Besides its intellectual center, the University of Chicago, you can visit the Robie House – a Frank Lloyd Wright design – and the Museum of Science and Industry, highlighted by the German submarine U-505, which was used in World War II.

Feast on meals by celebrity chefs

While most known for its pizza and hot dogs, Chicago boasts some of the top names in contemporary American cooking. Choose among Marcus Samuelsson's C-House, Rick Bayless (owner of Mexican exemplars Frontera Grill and Topolobampo) and Grant Achatz, whose trendsetting Alinea restaurant is renowned as one of the top 10 in the world.

Laugh out loud at Second City

The famous comedy club whose troupe has supplied Saturday Night Live with many cast members over the years, including John Belushi, Bill Murray, Gilda Radner, Mike Myers, and Tina Fey. On the other side of Old Town, the Steppenwolf Theatre Company puts on highly regarded modern drama; founding troupe members include Gary Sinise and John Malkovich.

Celebrate diversity in Chicago's ethnic neighborhoods

The City of Big Shoulders is also one of immigrants, and vitality can be found checking out some of the main streets in districts such as Andersonville, a Scandinavian-dominated area; Rogers Park, with Jewish, Russian and Indian populations; and Pilsen, a lively place settled by Germans that's now characterized by a working-class Mexican community living alongside artists.

Follow the trail of Frank Lloyd Wright in Oak Park

Wright created Prairie Style architecture, emphasizing natural light and horizontal lines, at his home and studio here, and 25 more Wright buildings dot this southern Chicago suburb, most of which are private homes. Take a tour of the studio or of his concrete Unity Temple, with an interior that continues the exterior's geometry.

Book a flight to Chicago with American Airlines today to discover more things to do in Chicago.

View more destinations

American Airlines Vacations