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Discover Why Chicago Is the Ultimate Summer Vacation Destination


Image by Milko Valnev via Trover

The “Windy City” is known less for its summer gusts than its glistening skyscrapers, picturesque views of Lake Michigan, and outdoor attractions that are best enjoyed in the year’s warmest months. It’s time to look toward the Midwest’s favorite city for an action-packed, summer getaway that will place you in the city and steps away from the sand.

The following four events, activities, and attractions are guaranteed to make your upcoming visit to Chicago the best summer getaway yet.

Hit the Town, Then the Beach 

Images of towering skyscrapers and shimmering office buildings make it difficult to imagine Chicago as a summer beach getaway, but the sandy shores of Lake Michigan offer an abundance of places to take a dip in crystal clear waters and construct sandcastles. Jackson Park’s 57th Street Beach is a favorite among locals and visitors for its easy access from downtown Chicago hotels through a pedestrian-friendly underpass and its abundance of concessions, restrooms, and lifeguards. Others venture to the South Side for kid-friendly fun at 63rd Street Beach, featuring free volleyball games, playgrounds, and an interactive spray fountain.

Explore Navy Pier When the Weather’s Nice 

Chicago’s famous Navy Pier is open year-round, but locals aren’t afraid to admit how much better it is in summer. This 1.5-mile-long outdoor boardwalk offers quirky tourist shops, iconic restaurants with outdoor seating, theaters, the Navy Pier Beer Garden, art, museums, carnival rides (including the Centennial Wheel ferris wheel), cruise boats, and games for all ages. Visitors can access Navy Pier by taking the Metra commuter rail to the CTA buses, which arrive directly at the pier. Parking is available on-site for personal vehicles as well.

Root for the Home Team 

No visit to the Windy City is complete without a visit to historic Wrigley Field. The home of the Chicago Cubs, Wrigley Field is known for its ivy-covered outfield wall and history dating back more than 100 years. You don’t have to be a Cubs fan to feel the infectious spirit of the Chicagoans, who view baseball more as a way of life than a game. Watch the die-hard fans, dine on tasty ballpark eats, spend time with your kids in the First Timers Booth, and admire the history of one of baseball’s most iconic stadiums. Whatever you do, don’t forget to root for the home team.

Become a Part of the Skyline

There’s no better way to experience Chicago’s skyline than to become a part of it. Admire some of the city’s best views from the Ravenswood neighborhood’s Fountainhead high-in-the-sky whiskey and beer-focused bar. Or take in some of the best views of Millennium Park and Lake Michigan from Cindy’s, a rooftop bar serving well-executed American eats from the top of the Chicago Athletic Association Hotel. From the Magnificent Mile to Lincoln Square, The Loop, and everywhere in between, there’s a Chicago bar or restaurant nearby that’s taking advantage of its outdoor space.

Chicago’s springtime excitement and temperatures are on the rise, which means it’s officially time to start planning your summer escape.

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