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Jun 13, 2025

Out and about in Chi-town

Be blown away by all the Windy City has to offer.


Getty Images 1421910139

Chicago is home to the AAD headquarters and the birthplace of the new Pope Leo XIV. But it boasts more for tourists beyond deep dish pizza and selfies at Cloud Gate (aka The Bean). Discover other exciting opportunities to include in your long weekend schedule.

Anchors aweigh

Navy Pier is a well-known Midwest destination, and for good reason. Situated on Lake Michigan, the area has something for everyone in the group or family, including restaurants, shops, boat cruises, sightseeing tours, and, of course, the 150-foot Ferris wheel. Visitors can view the beautiful backdrop lit up by fireworks in a free show on Wednesdays at 9 p.m. and Saturdays at 10 p.m.

Look out below

If it’s heights you’re looking for, don’t miss the chance to observe the city (and more) from above. Skydeck Chicago, located on the 103rd floor of the iconic Willis Tower, provides panoramas of up to four states. Those who are extra daring can step onto The Ledge — a suspended box with 1.5-inch-thick glass that is 1,300 feet above ground.

Family forward

Chicagoland may not be Disneyland, but it does have numerous activities for kids or kids at heart. The Lincoln Park Zoo, the Chicago Cultural Center, or Garfield Park Conservatory are entertaining and educational low- or no-cost options. Explore an acclaimed museum, such as Shedd Aquarium, Adler Planetarium, Art Institute of Chicago, or the Museum of Science and Industry. Stroll to Millennium Park or find a nearby playground, like Maggie Daley Park, to let the little ones burn some energy.

Breaking bread

Again, Chicago has dining options that are sure to please all palates. To satisfy cravings of local delicacies, check out Lou Malnati’s Pizzeria for a slice of pie, Portillo’s for a traditional Chicago-style hot dog, or get a pint of Goose Island beer at its dedicated taproom. For a celebrity experience (or possible sighting), make a reservation at Chef Art Smith’s Blue Door Kitchen & Garden, Chef Grant Achatz’s Alinea, or Next — winner of the James Beard Award for Best New Restaurant and a Michelin Star.

After hours

The Windy City is home to The Second City, the legendary improv-based sketch comedy company that has produced many famous entertainers. Hangouts such as Green Mill Jazz Club and The Redhead Piano Bar are great places to feast on live music or join in a sing-along, respectively. Sports lovers can visit Wrigleyville, which hosts themed bars, or take themselves out to a ballgame at Rate Field, where home team Chicago White Sox will battle the Cleveland Guardians.

The Magnificent Mile

This renowned shopping district stretches 13 blocks down Michigan Avenue from the Michigan Avenue Bridge to Oak Street. The street is dotted with giant fashion retailers along with restaurants, hotels, and galleries. Other popular shopping locales include: luxury-lined Oak Street, State Street and its Jeweler’s Row, the unique Armitage-Halsted Hub, and the historic Maxwell Street Market.

Visit Choose Chicago for more things to see and do around town.

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