The Windy City is a fantastic family destination regardless of the time of year and the age of the traveler. Warmer weather means sun and sailing on Lake Michigan, and bike rides through the easily traversable city. The cold of winter brings with it plenty of shopping, Christmas markets and the charm of a snowy Chicago. Whatever the season, though, here are a few things you’ll find fun for the whole family, all year-round.
Museums Galore
Chicago is filled with educational and entertaining museums. The Field Museum is capable of capturing the curiosity of anyone, starting with the giant T-rex, Sue, as soon as you walk in. More than 30 exhibits display the wonders of the natural world combined with fascinating historic artifacts. Nearby, the Adler Planetarium is a great spot to take your budding young astronaut, with the Sky Theater featuring VR journeys through the known universe. The Art Institute of Chicago is equally pleasing, combining recognizable works with modern art.
The Local Wildlife
While you can’t expect to come across too many animals while your family is running around Chicago, you can pay a visit to two beloved spots across the city to get your taste of worldwide wildlife. The John G. Shedd Aquarium features exotic fish from all over, but the real showstopper is the Oceanarium, with gorgeous views of Lake Michigan setting the stage for the dolphin displays. Across town, the Lincoln Park Zoo provides free entertainment all year, and recent expansions mean even more animals to catch your eye as you walk the well-maintained grounds.

Lincoln Park Zoo, Chicago. Photo: Jim Roberts | Dreamstime.com
Festival Frenzy
Chicago always has some sort of festival occurring, whether you prefer food, music, theater, shopping or a mix of it all. With Chicago Ale Fest and Chicago Restaurant Week in January; Theatre Week in February; the Chicago Beer Festival in March; and Baconfest Chicago in April, there’s plenty to do coming up in the next several months.
Major Fun at the Major Leagues
Baseball, basketball, hockey, football, soccer — take your pick. Chicago has the Cubs, White Sox, Bulls, Blackhawks, Bears and more, most just a short cab ride away from downtown, making it easy to catch a game in between shopping, museum visits and dining.
Great Views, Above and Below
If it’s the top views you’re after, you’re in luck. Chicago knows it’s pretty, and gives you several great vantage points for snapping photos. Try Navy Pier for a few hours, where you can walk up and down the pier, snacking your way through the many new restaurants added following its recent restoration. The choices are far from few, and you’ll even find a beer garden or two. Don’t forget to look behind you, though — that’s where you can see a large portion of the Chicago skyline, laid out in all its glory. Take a ride on the pier’s Ferris wheel for shots of both the skyline and the lake.
Want to get a little higher? Take a ride on one of the world’s fastest elevators to the top of Hancock Tower, where you can get a glimpse from the observatory. If you’re feeling particularly brave, you can step out onto the glass overlook and watch the world pass by below your feet.
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