25 Fun Things to Do in Chicago

In a city this amazing, the choices really are endless.

Photos courtesy of Choose Chicago

Skyscrapers of steel and glass tower over shimmering Lake Michigan. The crack of a bat echoes as the Cubs and White Sox vie for major league glory. Sunbathers laze along miles of sandy beaches. Ah, Chicago in the summer. It’s one of the best times to explore the nation’s third-largest city—a place full of new discoveries and classic experiences.

From buzzy outdoor music festivals to gritty blues joints, unparalleled art museums to floating architecture tours, you won’t soon run out of things to do in Chicago—in summer or any other time of year. Here are some of our favorites, and information about how to use your AAA Membership to upgrade your experience.

Go museum-hopping.

The Field Museum’s SUE is the largest Tyrannosaurus rex specimen ever found.

With so many things to do in Chicago, deciding where to go first can be tough. Luckily, many of the city’s world-class museums are clustered together, making it easy to immerse yourself in science, art, history and more.

Start at Chicago’s Museum Campus, home to three of the city’s most well-known attractions. The Field Museum holds a treasure trove of natural history, starring Maximo the titanosaur and SUE the Tyrannosaurus rex. At the Shedd Aquarium, tens of thousands of aquatic animals swim, waddle, crawl and paddle. And at the Adler Planetarium, you can touch a moon rock, peek inside the Gemini 12 spacecraft, and see planets and stars like you’ve never seen them before.

Just a few blocks away, the Art Institute of Chicago houses one of the world’s finest art collections, including works by the likes of Vincent van Gogh, Edward Hopper, Georgia O’Keefe and more. June 18–Aug. 15, 2021, the institute will display portraits of former President Barack Obama, painted by Kehinde Wiley, and former first lady Michelle Obama, painted by Amy Sherald, which were commissioned by and originally displayed at the Smithsonian Institution’s National Portrait Gallery.

Venture to the Hyde Park neighborhood, and you’ll find Chicago’s Museum Campus South, home to seven intriguing museums. Full of hands-on exhibits, the Museum of Science and Industry is the largest museum of its kind in the Western Hemisphere. Through Oct. 24, 2021, you can celebrate your favorite day-savers at the “Marvel: Universe of Super Heroes” exhibit. Among the other delights on campus: the Frederick C. Robie House, designed by Frank Lloyd Wright; the DuSable Museum of African American History; and the Oriental Institute Museum, the Smart Museum of Art, the Renaissance Society, and the Reva and David Logan Center for the Arts, all of the University of Chicago.

Pro tip for AAA Members: Save on tickets to select attractions, such as with the Chicago CityPASS that combines entry to five Chicago must-visit places.

Spend time in the parks.

The Cloud Gate sculpture in Millennium Park.

With more than 600 parks throughout the city, there’s never a shortage of things to do outdoors in Chicago—whether you’re looking for high-energy fun or a peaceful stroll. The city’s downtown gem is Millennium Park. This lakefront campus is home to the famous Cloud Gate sculpture (aka “The Bean”) by artist Anish Kapoor; Crown Fountain, designed by artist Jaume Plensa, with its larger-than-life video wall; flower-filled Lurie Garden; and kid-favorite Maggie Daley Park. Daley Park boasts a 40-foot climbing wall; an 18-hole miniature golf course; and the Skating Ribbon, a curvy path for walking and inline skating in summer (and ice-skating in winter).

Beyond downtown in the Woodlawn community, check out Jackson Park and its Japanese Garden filled with cherry trees. This lush space dates to 1893 when the Japanese government built a temple and small garden there as its pavilion for the World’s Columbian Exposition.

Pro tip for AAA Members: Whether you want takeout for a picnic in the park or prefer a dining experience that’s a bit fancier, the AAA Mobile app can help you find AAA Diamond restaurants near you.

Experience Chicago’s superlatives.

The Ledge at Skydeck Chicago gives you a view from 1,353 feet in the air.

The tallest, the largest, the highest—some Chicago attractions come with a “wow” factor that can’t be matched. Take Skydeck Chicago for example. The highest observation deck in the United States also features The Ledge, which lets you step outside the 103rd floor of Willis Tower with only glass under your feet. The jaw-dropping views can reach nearly 50 miles on a clear day and give you a glimpse of up to four states. Before heading up, explore Chicago’s history, culture, cuisine and architecture at Skydeck’s new interactive museum on the lower level of the tower.

A Chicago classic, the lakefront Navy Pier is home to 50 acres of rides, restaurants, shops, museum space and more. After a spin on the 200-foot-tall Centennial Wheel, stop for dinner and drinks at Offshore, home to the nation’s largest rooftop venue. The 36,000-square-foot space delights with panoramic views of Lake Michigan and the Chicago skyline.

If you prefer ground-level greatness, check out Garfield Park Conservatory—one of the largest botanical gardens in the country (and recently named the top garden in North America by Yelp). Indoors, you can wander amid thousands of plant species from around the globe in eight display gardens under glass. Outside, more than 10 acres hold outdoor gardens, play spaces for kids, a water lily pond and more.

Art lovers can experience contemporary works in a BIG way at Art on theMart, the largest permanent digital art projection in the world. A rotating gallery of images is projected on the 2.5-acre facade of theMart building—a breathtaking way to appreciate art during an evening stroll along the Chicago Riverwalk.

Gawk at the amazing architecture.

Chicago’s Pullman Historic District is the city’s only U.S. national monument.

Chicago is renowned worldwide for its abundance of architectural styles. The clean lines of modernism mingle with Beaux Arts, Victorian and even Gothic Revival—survivors of the Great Chicago Fire. For the best look at the city’s masterpieces, board Chicago’s First Lady for one of the Chicago Architecture Center’s river cruises. The boat takes you past more than 50 iconic buildings along the Chicago River, while guides share the structures’ fascinating histories.

Beyond downtown, seek out architectural gems like the Pullman neighborhood. Built in the 1880s as a planned industrial town for employees of the Pullman Company, which manufactured railcars, the area is now a historic district and Chicago’s only national monument. A self-guided walking tour reveals the many original buildings that remain, including company houses (from executive mansions to worker cottages) and the elegant Hotel Florence.

Another architecture-rich neighborhood to explore is Bronzeville, the heart and soul of Chicago’s African American community. The neighborhood’s historic district contains several buildings of landmark status, including the art deco Chicago Bee Building, once home to the Chicago Bee newspaper, founded by African American entrepreneur Anthony Overton.

Pro tip for AAA Members: Stay in amazing hotels—with a member-exclusive discount. Find the right one and book now.

Listen to melodious music.

The Green Mill Cocktail Lounge dates to 1907.

Of the many things to do in Chicago, seeking out live music might be one of the easiest. The city overflows with music venues, from downtown blues joints to sultry jazz clubs to festival-filled outdoor arenas. And since 2021 has been designated the Year of Chicago Music, it’s the perfect time to get in tune.

Start downtown in Millennium Park, where the Jay Pritzker Pavilion hosts a summer music series along with annual outdoor music festivals. This summer, Chicago in Tune, Aug. 19–Sept. 19, celebrates the city’s music scene with concerts at the pavilion as well as at venues around the city. Even if no one’s playing, you can stretch out on the Great Lawn and marvel at the pavilion’s Frank Gehry-designed crown of stainless steel panels and trellis of curving steel pipes.

For a more intimate experience, head to the Uptown neighborhood, where the Green Mill Cocktail Lounge has been hosting live jazz since 1907. This historic venue offers a speakeasy vibe that’s been captured in several TV shows and movies, including Ocean’s 12 and High Fidelity. Or, opt for blues at iconic Kingston Mines in Lincoln Park. Founded in 1968, it’s Chicago’s oldest continuously operating blues club.

Get some fresh air—and a little exercise, too.

Chicago’s many waterfronts, trails and green spaces make the city a perfect playground for active visitors. Get out and about along the pedestrian-friendly Chicago Riverwalk, which runs 1.25 miles along the south bank of the Chicago River. Grab an alfresco lunch by the water, explore a museum or even launch a kayak. You can rent one from Urban Kayaks for a leisurely river paddle past towering skyscrapers or opt for a guided tour with a quick kayaking lesson and insights into the city’s history and architecture.

Downtown isn’t the only place to find waterfront fun. Chicago’s 26 lakefront miles include more than two dozen free beaches. Those who enjoy recreation on the water will want to head to Margaret T. Burroughs Beach to rent personal watercraft, pontoon boats, kayaks and paddleboards. Animal lovers, head north to Montrose Beach. After kayaking or stand-up paddleboarding on the lake, you can birdwatch at Montrose Point Bird Sanctuary and dote on puppies at the dog park.

Bicyclists looking for things to do in Chicago should pedal on over to the Lakefront Trail. This 18-mile paved path follows the Lake Michigan shoreline past peaceful nature sanctuaries, bustling boardwalks, parks, beaches and more. (Don’t miss the new Navy Pier Flyover; the new elevated path helps walkers and bikers navigate the trail near Navy Pier more safely.) Or head to Chicago’s northwest side for a spin along The 606. What was once an abandoned railway line is now a 2.7-mile elevated park and trail winding through some of Chicago’s hippest neighborhoods.

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