Ultimate Guide to the Best Things to Do in Chicago: Unmissable Attractions and Experiences

Ultimate Guide to the Best Things to Do in Chicago: Unmissable Attractions and Experiences

By Jack
10 min read

Step into Art History at the Art Institute of Chicago

The Art Institute of Chicago is one of the oldest and most comprehensive art museums in the United States, housing more than 300,000 works of art from around the world. Founded in 1879, this institution is a gem for art lovers, offering galleries filled with classic masterpieces as well as contemporary collections.

Highlights of the Collection

  • Impressionist and Post-Impressionist Art: Home to one of the largest collections outside of France, featuring works by Monet, Renoir, and Degas.
  • American Gothic: Grant Wood’s iconic painting, beloved for its portrayal of Midwest Americana.
  • Modern Wing: A striking contemporary structure designed by Renzo Piano, housing works from artists like Picasso and Warhol.

Visitor Tips

Plan to spend at least a few hours here, as the museum is expansive. Check the website for guided tours or audio guides to enrich your visit.

The grand entrance of the Art Institute of Chicago, featuring its iconic bronze lion statues and classical architecture.

Walk the Chicago Riverwalk for Views and Vibrancy

Stretching over a mile along the Chicago River, the Riverwalk is a scenic pathway offering unparalleled views of the city’s impressive architecture, delightful dining, and recreational activities.

Must-Visit Riverwalk Stops

  • Kayaking and Boat Tours: Book a kayak or take a guided river tour to view the skyline from the water, with narration that provides insights into the city’s architectural history.
  • Public Art Installations: The Riverwalk features rotating art installations that enhance its urban charm, making each visit unique.
  • Dining Along the Water: From casual eateries like Tiny Tapp to the more refined City Winery, the Riverwalk offers a diverse range of dining options with waterfront views.
A lively scene along the Chicago Riverwalk, featuring waterfront cafes, lush greenery, and iconic skyscrapers reflected in the river.

Experience the Skydeck at Willis Tower

Once the tallest building in the world, the Willis Tower (formerly known as the Sears Tower) offers breathtaking views of Chicago and beyond from its Skydeck. Located on the 103rd floor, the Skydeck is famed for its glass balconies, known as The Ledge, that extend four feet outside the building, giving you a heart-pounding view 1,353 feet above the ground.

Why Visit the Skydeck?

  • Unobstructed Views: See as far as four states on a clear day, and enjoy panoramic views of Lake Michigan, the Chicago River, and the downtown skyline.
  • Unique Photo Opportunities: Capture unforgettable photos with the cityscape as your backdrop.
  • The Ledge Experience: Step onto this all-glass box if you’re looking for an adrenaline rush.

Insider Tips

To avoid long lines, consider visiting early in the morning or during off-peak hours. Purchasing tickets online can also save you time on arrival.

A breathtaking view from the Skydeck at Willis Tower in Chicago, featuring the glass-bottom Ledge with panoramic city views.

Visit Millennium Park and Admire Cloud Gate

Millennium Park, a part of the larger Grant Park, is home to some of Chicago’s most beloved attractions, including Cloud Gate, affectionately known as “The Bean.” Designed by artist Anish Kapoor, Cloud Gate reflects the skyline and creates an interactive experience as visitors walk around and under it.

Other Must-See Features

  • Crown Fountain: This multimedia fountain features changing LED faces of Chicagoans and is especially popular during the summer when children can play in the water.
  • Jay Pritzker Pavilion: An architectural marvel that hosts free concerts during the summer, including the Grant Park Music Festival.
  • Lurie Garden: This 5-acre garden is a peaceful oasis filled with native plants, designed to represent Chicago’s motto, “Urbs in Horto” (City in a Garden).

Best Time to Visit

Millennium Park is open year-round, but summer is particularly lively with concerts, art installations, and festivals. Winter visitors can enjoy ice skating at the McCormick Tribune Ice Rink nearby.

A vibrant view of Cloud Gate, also known as “The Bean,” reflecting the Chicago skyline and visitors at Millennium Park

Explore Chicago’s Iconic Neighborhoods

Chicago’s neighborhoods reflect its cultural diversity, each offering a unique blend of food, art, and history. From the artsy murals of Pilsen to the historic sites of Bronzeville, exploring these areas offers a deeper connection to the city’s heritage.

Notable Neighborhoods

Chinatown: A must-visit for foodies, Chinatown is filled with authentic Chinese restaurants, shops, and the colorful Chinatown Square.

Pilsen: Known for its Mexican-American heritage, colorful murals, and authentic cuisine. Stop by the National Museum of Mexican Art for cultural insights.

Wicker Park and Bucktown: Hip and eclectic, these neighborhoods are packed with indie shops, bookstores, art galleries, and vintage boutiques.

A vibrant street scene in Chicago’s Wicker Park neighborhood, featuring boutique shops, colorful murals, and outdoor cafes.

Revel in Nature at Lincoln Park and Lincoln Park Zoo

As the largest public park in Chicago, Lincoln Park offers a vast green space for relaxation, recreation, and exploration. The Lincoln Park Zoo, one of the nation’s oldest and free to the public, is home to animals from around the world.

Attractions within Lincoln Park

Nature Boardwalk: A restored ecosystem around a pond, offering a haven for local wildlife and a beautiful spot for a walk.

Lincoln Park Zoo: The zoo hosts a variety of animals, from polar bears to giraffes. It’s open year-round and often hosts seasonal events.

Chicago History Museum: Located within Lincoln Park, this museum provides fascinating exhibits on Chicago’s history.

A serene view of Lincoln Park in Chicago, featuring lush greenery, a tranquil pond, and the skyline in the distance, with Lincoln Park Zoo nearby

Visit Navy Pier for Fun and Festivities

Navy Pier is one of Chicago’s most popular attractions, offering a range of entertainment options including a Ferris wheel, dining options, and seasonal events. Originally built as a cargo facility, Navy Pier has transformed into a dynamic recreational space.

What to Do at Navy Pier

  • Centennial Wheel: This iconic Ferris wheel provides panoramic views of the city and is especially enjoyable during sunset.
  • Chicago Children’s Museum: Perfect for families, offering interactive exhibits and educational activities.
  • Crystal Gardens: An indoor botanical garden with fountains, palm trees, and lush greenery.

Seasonal Events

Throughout the year, Navy Pier hosts fireworks displays, holiday markets, and summer music series, making it a hub for family-friendly activities.

A vibrant scene at Navy Pier in Chicago, featuring the iconic Ferris wheel, bustling visitors, and views of Lake Michigan.

Enjoy Chicago’s Diverse Food Scene

No visit to Chicago is complete without sampling the city’s iconic dishes. From deep-dish pizza to fine dining, Chicago offers an array of culinary experiences that are as rich and varied as its neighborhoods.

Must-Try Dishes

Italian Beef Sandwich: A sandwich overflowing with thinly sliced beef and au jus, often topped with giardiniera (Italian pickled vegetables). Try Al’s Beef for an authentic taste.

Deep-Dish Pizza: A Chicago staple, with thick, buttery crusts and layers of cheese and sauce. Popular spots include Lou Malnati’s and Giordano’s.

Chicago-Style Hot Dog: An all-beef hot dog “dragged through the garden,” topped with mustard, onions, relish, tomatoes, pickles, and peppers on a poppy seed bun—never ketchup.

Discover Science and History at the Museum of Science and Industry

Located on the South Side, the Museum of Science and Industry is a must-see for those interested in technology and innovation. Housed in the former Palace of Fine Arts from the 1893 World’s Columbian Exposition, this museum offers hands-on exhibits across a range of scientific topics.

Highlights of the Museum

The Coal Mine Exhibit: A re-creation of a coal mine that takes you underground to learn about the history of mining in the U.S.

U-505 Submarine: This real German WWII submarine offers an interactive tour that provides insights into naval history.

Science Storms: An exhibit that recreates natural phenomena such as tornadoes, lightning, and tsunamis.

The grand exterior of the Museum of Science and Industry in Chicago, surrounded by lush greenery and a clear blue sky.

Catch a Game or Tour at Historic Wrigley Field

For sports fans, visiting Wrigley Field is essential. Built in 1914, this baseball stadium is one of the oldest in the country and is home to the Chicago Cubs. Even if there isn’t a game during your visit, Wrigley Field offers stadium tours that provide a behind-the-scenes look at its storied past.

Why Wrigley Field?

Neighborhood Vibe: Known as “Wrigleyville,” the area surrounding the stadium is filled with sports bars, restaurants, and shops dedicated to Cubs culture.

Game Day Atmosphere: Cubs games are known for their energetic fans and historic traditions.

Behind-the-Scenes Tours: Walk through the press box, dugouts, and outfield for a comprehensive look at the stadium’s history.

The iconic exterior of Wrigley Field in Chicago, with its famous marquee and excited fans gathering for a game.

Take a Scenic Cruise on Lake Michigan

A lake or river cruise offers an entirely different perspective on Chicago’s skyline and architecture. Architectural cruises along the Chicago River are led by expert guides who provide insights into the city’s famous buildings and unique history. Lake Michigan cruises offer spectacular views of the skyline and are especially popular at sunset.

Types of Cruises

Dinner and Brunch Cruises: Enjoy a meal while taking in Chicago’s iconic views.

Architectural River Cruises: Ideal for learning about Chicago’s architectural heritage and seeing the buildings up close.

Lake Michigan Sunset Cruises: A perfect choice for romantic views of the city as the sun sets.

Admire the Exhibits at the Field Museum of Natural History

The Field Museum, located in Grant Park, is a premier destination for those fascinated by history, anthropology, and natural sciences. Its collection includes everything from ancient Egyptian artifacts to towering dinosaur skeletons.

Must-See Exhibits

Cyrus Tang Hall of China: This exhibit dives deep into the history, culture, and innovations of ancient and modern China.

SUE the T. rex: The largest and most complete Tyrannosaurus rex skeleton ever discovered, now on display in a dedicated exhibit.

Inside Ancient Egypt: A meticulously designed exhibit that transports visitors to the world of ancient Egypt, featuring authentic artifacts and a replica tomb.

The grand entrance of the Field Museum of Natural History in Chicago, featuring its iconic columns and banners showcasing current exhibits

Final Thoughts: Discover Chicago’s Endless Wonders

Chicago’s multitude of attractions and experiences make it an ideal destination for travelers seeking culture, history, and excitement. From museum marvels and architectural cruises to vibrant neighborhoods and culinary delights, the Windy City guarantees unforgettable memories.

FAQs

When is the best time to visit Chicago?

May to October is ideal for outdoor activities, with warm weather, festivals, and fewer crowds in early fall.

Are there free museums in Chicago?

Yes, some museums have free admission days, like the Lincoln Park Zoo and Chicago Cultural Center. Check specific museum websites for details.

What’s the easiest way to get around?

Chicago’s “L” trains, buses, and bike-sharing make it easy to explore without a car. Walking and public transit are best for reaching major attractions.

About the author
Jack
Hi, I’m Jack from LensandTravel! I share travel inspiration, guides, and photography tips to help you explore new destinations and capture stunning visuals. Let’s create together!

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