Say hello to the Windy City

What to do in Chicago

Chicago’s landmarks and activities should put the Windy City on every traveler’s list. Whether you’re a history buff, art aficionado, or sports fan, you’ll find plenty to keep your interest in America’s third-largest town.

Start your trip at Cloud Gate, also affectionately referred to as “The Bean.” Located in Millennium Park, the massive stainless-steel sculpture is a photo every Chicago first-timer needs. From there, breathe in the beauty of Lake Michigan as you saunter down Navy Pier for local eats and a ride on the Centennial Wheel.

Looking for the city’s best view? Head to Skydeck at the 1,450-foot-tall Willis Tower—formerly Sears Tower—which stood as the world’s tallest building from 1974 until 1998. Yes, the city views are amazing. But it’s the step out onto The Ledge and the view straight down that will flip your stomach.

Love music? This year’s Lollapalooza in Grant Park runs July 28–31. The annual music festival becomes a city unto itself. Miley Cyrus, Marshmello and Modest Mouse are on this year’s ticket—and that’s just musicians starting with M!

For a quieter atmosphere, make your way to the Art Institute of Chicago, where you can bask in Impressionist and post-Impressionist works by Monet, Seurat, Renoir, Degas, and Van Gogh.

And then there’s sports. Michael Jordan’s six NBA championships with the Bulls put Chicago on the map, but the Bears (NFL), Blackhawks (NHL), and Cubs and White Sox (MLB) keep sports fans pumped. Want to root for Seattle during your visit? The Mariners play at the White Sox on April 12–14. Runners can target the Chicago Marathon, held every October and the world’s fourth-largest race by number of finishers.

Finally, don’t forget a Chicago Dog, complete with signature poppyseed bun, mustard, relish, onions, pickles, and tomatoes. Pro tip: If you want to blend in with the locals, hold the ketchup!

To visit a club, members must request a letter of introduction. Log on to Submit club reviews at

More Featured Reciprocal Clubs

Reciprocal Club: London, Ontario
Reciprocal Club: Philadelphia, PA
Reciprocal Club: Norfolk, Virginia