Chicago is racking up world-class accolades. So we've put together a checklist of classic Chicago activities that include the best of the best.

Whether you are planning a Chicago travel itinerary for a half day, weekend or multi-day stay, these are some of the many must-sees while in the Windy City. But just as Chicago is unique, we invite you to put your personal stamp on your Chicago adventure. So let the fun begin!

Spectacular sightseeing

The Ledge

Visit the second tallest building in North America at the Willis Tower and step out onto The Ledge, a suspended glass box at the Skydeck Chicago observatory that is more than 1,000 feet in the sky. Or brace yourself for the newest thrill experience TILT! at 360CHICAGO. The moving glass enclosure leans you over the edge of 875 N Michigan (formerly the John Hancock Center) and is the first of its kind in the world.

Take a stroll around Buckingham Fountain in Grant Park and enjoy the colorful light and music display as it glows against the backdrop of Chicago's skyline and lakefront. Inspired by the Latona Basin at Versailles, but twice the size as its counterpart, it is one of the largest fountains in the world and one of the city's favorite icons.

Ford the Chicago River by boat tour and explore Chicago's architectural wonders on the only river in America that flows backwards. The reversal of the Chicago River was a pioneering, massive public works effort that saved the Chicago region from waterborne diseases in the early 1900s.

Ride on the Ferris wheel at Navy Pier. It's modeled after the very first Ferris wheel built for Chicago's 1893 World's Columbian Exposition. Rides, shops, restaurants and boat tours abound at the Midwest's number One attraction.

Loop up and around on an architecture tour. Chicago was home to the world's first skyscraper and while it no longer stands (the iron-and-steel-framed Home Insurance Building stood downtown from 1884-1931), the city's skyline is one of the most recognizable and is filled with architectural treasures of the past and present.

Roar with the lions at one of the country's oldest public zoos, which is also one of the last free zoos in the nation. Offering an unforgettable wildlife experience amid a stunning urban skyline, the scenic Lincoln Park Zoo is open to the public for free every day of the year. 

Chicago is home to 77 community areas containing more than 100 neighborhoods, each brimming with their own unique attractions, traditions and histories, including Chinatown — one of the largest in North America — and Boystown — the first officially recognized gay community in the U.S. Go on a culture crawl without leaving Chicago with an itinerary that includes a neighborhood tour

Innovative outdoor park spaces

Crown Fountain

Snap a selfie in front of "the Bean," the famous sculpture known officially as Cloud Gate, at its home in Millennium Park. Also check out the Jay Pritzker Pavilion for a free performance, connect with nature in Lurie Garden, and cool off in Crown Fountain, the glass towers that spout water from its digital faces. Millennium Park is constructed on top of a railroad yard and expansive parking garages — making it one of the largest green roofs in the world.

Runners, bikers, strollers: join the fun on The 606. A 2.7-mile long railway that was newly converted into a stunning path set above neighborhood streets, it is the nation's longest elevated park system. 

Combining elements of whimsy reminiscent of Alice in Wonderland or Charlie and the Chocolate Factory, Maggie Daley Park (located just west of Millennium Park) is one of the newest kid-approved attractions in Chicago. This super playground can't be missed with it's towering play bridges, sky-high slides and a rock climbing wall that is one of the largest outdoor climbing structures in the world.

While most cities build industrially all the way up to their respective waterfronts, Chicago's lakefront has been preserved as a playground forever free and open to the public. Chicago boasts 26 miles of shoreline, 33 sandy beaches and an 18-mile long bike/running path along Lake Michigan to explore during the warmer weather months.

Arts & Culture

Art Institute of Chicago

Take pleasure in one of the world's finest and largest collections of French Impressionist paintings at The Art Institute of Chicago. And while you're there, explore the architecturally stunning Modern Wing, which allows the Art Institute to house great collections of modern and contemporary art.

In the Chicago Cultural Center, the nation's first free municipal cultural center, look up at the world's largest Tiffany art glass dome for a sparkling masterpiece created with nearly 30,000 pieces of stained glass and browse the numerous halls filled with music and art exhibits.  

Feel the power of Chicago's dazzling theater scene. As the nation's only city with five Regional Tony Award-Winning theater companies — including Goodman Theatre, Victory Gardens Theater, Chicago Shakespeare Theater, Lookingglass Theatre Company and Steppenwolf Theatre Company — Chicago delivers unforgettable performances every day of the week.  

The term "Jazz" was first coined in Chicago in 1914. Check out the many live jazz clubs across the city that keeps this great music tradition alive. 

Submerge yourself in the U-505 German Submarine at the Museum of Science & Industry, the largest science museum in the Western Hemisphere.

Find yourself Deep in Space at the Adler Planetarium's Grainger Sky Theater. As the world's most advanced digital theatre, the Grainger boasts images that are eight times sharper than your digital cinema.

Dive in to a coastal environment of Beluga whales, dolphins, sea otters, and seals at the Shedd Aquarium's 3-million-gallon saltwater Oceanarium, the largest Indoor marine mammal habitat in the world.

Pay a visit to the largest, most complete, best preserved T. rex ever discovered. You can meet the T. rex named Sue at The Field Museum. Don't worry, she doesn't bite.  

A Culinary Epicenter

Hot Dog

The "Oscars of the food world" are the James Beard Foundation Awards and our city is proud to boast over 40 James Beard award winnersChicago chefs, restaurants and restaurateurs are truly among the best in the nation.

Chicago is one of only four U.S. cities to have its own Michelin Guide, an international standard for excellence. Build your dine-around itinerary with prestigious Michelin-star Chicago restaurants

Indulge in some cheesy goodness at the famous pizzerias that serve up our award-winning Deep-Dish Pizzas, Chicago originals with layers of cheese and buttery crust over an inch thick. Who serves up the best pies? That's for you to decide!

Classic local eats also include the Chicago-style Hot Dog, which piles on a whopping seven toppings! For authenticity you'll find: yellow mustard, chopped onions, bright green sweet relish, a dill pickle spear, tomato slices, spicy pickled sport peppers and a dash of celery salt. And absolutely no ketchup.

Smell the wonders of Chicago's famous Chicago Mix before you even reach the storefront door at Garrett Popcorn Shops. The intriguing blend of caramel and cheese popcorn is well worth the wait.

Need more proof of our culinary pedigree? How about the fact that Chicago has over 4,700 restaurants, with new ones popping up nearly every week. Taste test through the top spots earning accolades for Chicago from experts like Forbes Travel Guide, AAA Diamond awards and Zagat best lists.

From television personalities (Top Chef winner Stephanie Izard and television personality Chef Rick Bayless) to ethnic cuisines of every flavor and beloved foodie events (such as Taste of Chicago and Chicago Gourmet) — our dining scene is a showcase of the best and the brightest.

Related Listings

Buckingham Fountain
Columbus Dr. and Congress Parkway
Chicago, IL 60603
(312) 742-4847

Navy Pier
600 E. Grand Ave.
Chicago, IL 60611
(312) 595-5300

Millennium Park
201 E. Randolph St.
Chicago, IL 60601
(312) 744-6050

Adler Planetarium
1300 S. Lake Shore Dr.
Chicago, IL 60605
(312) 922-7827

Museum of Science and Industry
57th Street and Lake Shore Dr.
Chicago, IL 60637
(773) 684-1414

The Field Museum
1400 S. Lake Shore Dr.
Chicago, IL 60605
(312) 922-9410

360 CHICAGO (formerly John Hancock Observatory)
875 N. Michigan Ave.
Chicago, IL 60611
(888) 875-8439

Skydeck Chicago
233 S. Wacker Dr.
Chicago, IL 60606
(312) 875-9696

Garrett Popcorn Shops
625 N. Michigan Ave.
Chicago, IL 60611
(312) 944-2630

Art Institute of Chicago
111 S. Michigan Ave.
Chicago, IL 60603
(312) 443-3600

Shedd Aquarium
1200 S. Lake Shore Dr.
Chicago, IL 60605
(312) 939-2438

Lincoln Park Zoo
Cannon Dr. at Fullerton Parkway
Chicago, IL 60614
(312) 742-2000

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