Jason Lindsey / Alamy
Amy Tara Koch
August 12, 2014

For families, Chicago’s famous zoo, lush parks, interactive museums, lakefront beaches, and triumphant sports teams provide endless entertainment no matter the season. In this well-connected hub, getting around is half the fun. Take the kids around on their first trip to the Second City with a ride above ground on the El train, or enjoy of the balmy temperatures in summertime and tour the city’s outdoor sights (architecture, public art installations) by foot. Drop by Navy Pier, and picnic later at Grant Park. Check out Wrigley Field, and take advantage of the always-free, always-open Lincoln Park Zoo. If you’re in town during a frigid winter week, tough it out Chicago-style and enjoy ice skating at Millennium Park, or get a guided (heated) trolley tours. Fill your afternoons with museum visits and warm up in the evening with frothy hot chocolate at any one of the cafes lining Michigan Avenue. Fuel-up after a packed day with a family-sized Chicago-style deep-dish pizza.

Willis Tower Skydeck

All children wish they could fly like Peter Pan. At the Willis Tower Skydeck, this dream can be realized. Step out on the ledge, a staggering 103 floors and 1,353 feet high, and feel as though you are soaring over the city. On a cloudless day, it is possible to see clearly into three neighboring states: Indiana, Wisconsin, and Michigan.

Chicago Children’s Museum at Navy Pier

Dedicated to the art of play, exhibits such as WaterWays (pulleys and pipes, toy boats) and the Artabound Studio (paint, clay, and draw with trained art professionals) are hands-on experiences that encourage experimentation and creative thinking. The Tinkering exhibit is DIY-bliss for pint-sized inventors. Kids are invited to grab real tools and everyday materials, and to transform them into new objects. 

Peggy Notebaert Nature Museum

For science buffs, this Lincoln Park museum is paradise. Amble through ecosystems, bird watch with binoculars, and get wet while learning about river flow. The piece de resistance is the Judy Istock Butterfly Haven, a 2,700 square foot greenhouse with 1,000 butterflies from 11 different countries. Watch them flit around their tropical habitat and move slowly; one of these vibrant specimens might land on your shoulder. 

Behind-the-Scenes Wrigley Field Tours

Almost nothing symbolizes a Chicago-experience more than a hot dog (with all the fixings) and an afternoon baseball game. In 2014, Wrigley Field celebrated its 100th year, and offers fans a chance to sit in the dugout, step onto the field, visit the press box, and learn the inside truth about the infamous Curse of the Goat. 

Lincoln Park Zoo

With more than 1,250 animals, Lincoln Park Zoo ranks as one of the finest in the country. Don’t miss the Endangered Species Carousel or Regenstein African Journey—an interior exhibit that mirrors a safari experience. Afterward, meander over to the Nature Boardwalk where wooden pathways span a pond filled with wildlife, including largemouth bass and fathead minnows. 

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