A Cheapskate in Chicago

One June morning, I went to see what the tourists were up to in Chicago, where I live. My mission was to join them while adhering to a strict travel budget. So I started with a free Chicago Greeter tour of the downtown Loop, ground zero for visitors and home to popular attractions like Millennium Park and the Art Institute of Chicago.

Run by Choose Chicago, the city’s tourism marketing organization, the Greeter program pairs visitors with a local volunteer for a guided walk. Our guide, Janice Rosenberg, led me and eight visitors from Spain, Mexico and France on a 90-minute walk around the Loop. She pointed out famous sites like the Millennium Park sculpture by Anish Kapoor, “Cloud Gate,” known as “The Bean,” and hidden gems like the “Rushmore” mural, by the painter Kerry James Marshall, devoted to the women who have shaped Chicago. Ms. Rosenberg also identified hallmarks of classic Chicago architecture, including windows designed to catch lake breezes before air-conditioning was universal, and explained to the Europeans that a department store built in 1893 “is old for us.”

It was a dense serving of Chicago history and culture at an unbeatable price (though tips are welcome; I contributed $5).

Big cities, generally, are good places to cheap out as a traveler. Transportation options tend to be affordable. Chicago’s L train, for example, costs $2.50 a ride; day passes are $5.

And Chicago, newly popular with set-jetting fans of the restaurant-focused FX series “The Bear,” anchors the Midwest, a region known for its thrift. There are plenty of things to splurge on — the venerable Lyric Opera of Chicago or Michelin-starred restaurants — but you can experience excellence here in music, art, theater, food and more without digging deep into your pockets.

I spent a recent week living — and scrimping — like a tourist in Chicago. Here are some of my recommendations on how to save.