First-time visitor’s guide to Chicago

First time in Chicago? This guide’s for you. We’ve got all your must-see sights and experiences, whether you’re here for a day, a weekend, or a week.

Chicago is one of America’s great urban destinations. We’re a city known for our wide-ranging cultural impact — an influential music scene, iconic architecture, a world-class dining scene, just to start — so there’s a lot of ground to cover. A good first-time visit will give you a little taste of everything (with plenty left to do on your next visit).

Chicago itinerary Inspiration

Ready to start planning your first visit to Chicago? This sample itinerary offers some inspiration, but feel free to mix and match based on your interests!

To make the most of your inaugural visit, add these attractions, experiences, and events to your itinerary.

Things to do in Chicago for first-time visitors

Check out these top things to do in Chicago for first-time visitors all year round. And make sure to check out seasonal happenings, like holiday markets, music festivals, sporting events, and more to customize your itinerary to the time of year.

Explore the Millennium Park Campus

Millennium Park is classic Chicago, with a long list of iconic things to see and do. Splash around in Crown Fountain, grab a spot in the grass and enjoy free live music, wander a hidden garden, and say hi to “The Bean.” Plus, you’ll be in a prime location to stop into top museums and downtown spots.

First-time visitors guide to Millennium Park:

• Snap a selfie with Cloud Gate, aka “The Bean,” one of Chicago’s most iconic sights.
• Check the calendar for the Pritzker Pavilion, which hosts free movies, concerts, and fitness classes in the summer.
• Admire Crown Fountain, two towering sculptures that blend video and water into interactive art.
• Lurie Garden offers a peaceful oasis tucked away from the hustle and bustle.
• McCormick Tribune Plaza is a popular beer garden in the summer and a free ice rink in the winter.

On the southern edge of the park, the Art Institute of Chicago is a must-visit for first-time and returning visitors alike. The renowned collection spans global art styles, with an Impressionist gallery that rivals the Louvre.

Tip: Wonder what’s on the other side of that long, winding bridge? Follow the snake-like structure to Maggie Daley Park, a whimsical lakefront haven with rock climbing, tennis, mini golf, a playground, and more. It’s also home to the famous ice skating ribbon in the winter.

Check out Navy Pier and the lakefront

Navy Pier is a must-see Chicago destination. This family-friendly attraction has endless options for things to see and do: scenic boat rides on the lake, summer fireworks displays, outposts of local dining options, the largest rooftop bar in the country, free outdoor music, carnival rides, and so much more.

First-time visitors guide to Navy Pier:

• The Centennial Wheel is one of Navy Pier’s most famous sights. Soaring nearly 200 feet in the air, this climate-controlled ride is inspired by the world’s first Ferris wheel that debuted at Chicago’s World’s Fair.
• Bring the kids to more classic rides at Pier Park or the whimsical and interactive Chicago Children’s Museum.
• Grab tickets for the latest show at the Chicago Shakespeare Theater, featuring traditional stories and modern adaptations.
• See the city in a whole new way with the immersive Flyover Chicago.
• Offshore Rooftop, the world’s largest rooftop bar, is the perfect spot to soak in the lakefront views.

Another favorite: summer fireworks displays every Wednesday and Saturday from Memorial Day to Labor Day. They’re especially jaw-dropping when watched from the deck of one of Navy Pier’s many boat tours.

Weather permitting, this is a great opportunity to explore the city’s scenic lakefront. Rent a bike, join a bike tour, or just take a stroll along the Lakefront Trail, a popular pedestrian path that hugs the Lake Michigan shoreline.

Tip: Looking for an easy way to make the most of your time in Chicago? Big Bus Tours offers a convenient hop-on, hop-off sightseeing experience that’s perfect for first-time visitors.

Stroll the Chicago Riverwalk

The Chicago Riverwalk is a must-do during your Chicago visit, no matter how many times you’ve been to the city. In the summer, you’ll find locals and visitors stepping onto boat tours, sipping wine on waterfront patios, and soaking in the incredible city vibes.

First-time visitors guide to the Chicago Riverwalk:

• Grab a bite or a drink on one of the many outdoor bars and restaurants on the Riverwalk.
• Hop on a kayak rental or tour to see the skyline from a whole new vantage point.
• Take an architectural boat tour to learn the stories behind the city’s most famous riverfront landmarks.
• See the inner workings of the city’s famous movable bridges at The McCormick Bridgehouse Museum.
• In the evening, view the largest video-projected artwork in the world during Art on the MART.

Tip: The Chicago Riverwalk is a popular starting point for many river boats, from informative architecture tours to lively tiki-themed cruises. Find your perfect boat tour.

Visit top Chicago museums

No visit to Chicago is complete without a visit to at least one of our biggest museums.

A good first stop is the Museum Campus — three world-class cultural institutions sitting on the scenic shores of Lake Michigan. The Field Museum, Shedd Aquarium, and Adler Planetarium are all excellent places to spend an afternoon.

Another top museum is the Art Institute of Chicago, located right next to Millennium Park. Further down the lakefront, the Griffin Museum of Science and Industry attracts science lovers of all ages.

First-time visitors guide to Chicago’s museums:

• The Field Museum is home to icons like Máximo the Titanosaur and SUE the T.rex.
• Meet sharks, belugas, stingrays, and more aquatic creatures at the Shedd Aquarium.
• Get tickets for a Dome Show at the Adler Planetarium, the country’s oldest planetarium.
• The Art Institute of Chicago is the country’s second-largest art museum with a world-class collection of iconic works.
• At Museum Campus South, the Griffin Museum of Science and Industry is one of the largest science centers in the Western Hemisphere.

Tip: The Shoreline Sightseeing Water Taxi is the most scenic way to get to and from the Museum Campus. This seasonal vessel runs daily in the warmer months, connecting museum-goers to Grant Park and Navy Pier.

Admire the view at observation decks

Chicago has two adrenaline-pumping observation deck experiences, located in some of the city’s tallest skyscrapers. Both offer unique thrills, jaw-dropping views, and an excellent overview of Chicago’s architectural legacy.

First-time visitors guide to Chicago observation decks:

• Skydeck at Willis Tower (known by locals as the Sears Tower) invites you to literally step out on The Ledge, a glass box that extends from the skyscraper’s facade hovering over 1,300 feet above ground level.
• 360 CHICAGO, located within 875 N. Michigan Ave. (formerly the John Hancock Center), tips you out and over The Magnificent Mile, and affords views over the city and Lake Michigan from 1,000 feet up.

Tip: Make sure to get your tickets ahead of time! Both spots offer timed tickets and popular slots tend to book up quickly. Sunset is a popular time to go — you can enjoy the view in the day, then watch the city light up as dusk falls.

Take a boat tour

Some of the best views of Chicago are from the water. Whether you want to learn about the city’s history, get the inside scoop on the city’s rich architectural legacy, watch fireworks over the lake, or simply kick back and take in the sights, there’s a boat cruise in Chicago for you.

First-time visitors guide to Chicago boat tours:

• Architecture cruises are one of the best ways to see the city and learn all about our legendary skyline.
• Dinner cruises are perfect for date nights, holidays, and special occasions, with jaw-dropping views, live music, and more.
• Kayaking and paddleboarding are popular ways to explore Chicago’s river and lakefronts. Rentals and tours are available.
• Boat rentals let you be your own captain for the day. Check out unique options (like the viral hot tub boats) from Chicago Boat Company.

Tip: Some water-based activities, like kayaking and paddleboarding, are seasonally available. Most boat tour companies operate from March through November, while some of the dinner cruises run year round.

Visit one of Chicago’s vibrant neighborhoods

Chicago is a city of neighborhoods, and no visit is complete without checking out one of our diverse enclaves. Each neighborhood has its own distinct culture, history, and vibes, so there’s guaranteed to be one that will spark your interest. No matter which you pick, you’ll get a slice of authentic Chicago life and spend the day living like a local.

First-time visitors guide to Chicago neighborhoods:

• Immerse yourself in Hispanic heritage in Little Village, the “Mexico of the Midwest”, or the hip Pilsen neighborhood.
• Visit the historic Chinatown area, overflowing with modern and traditional Chinese cuisine.
• Explore like a local in Logan Square and Wicker Park, neighboring enclaves known for their buzzy dining scenes.
• Discover popular lakefront enclaves like Lincoln Park and Lakeview, filled with family-friendly spots and waterfront parks.
• Enclaves like Andersonville and Edgewater are known for storefront theatres and quirky shopping.
• Hyde Park is a cultural mecca, home to the University of Chicago and the new Obama Presidential Center campus.

Tip: Not sure where to start? Chicago Greeter offers free neighborhood visits, led by friendly locals. Tours can be customized for language, interests, and more.

See a show: theatre, improv, music, and more

Theatre is the soul of Chicago, home to a diverse and dynamic array of performing arts groups and theatres. With hundreds of neighborhood venues and more Tony Award-winning theatres than any other city, Chicago offers something for everyone, every day of the week.

First-time visitors guide to Chicago theatre:

• Broadway In Chicago brings touring hits (and soon-to-be-hits) to historic downtown stages.
• The birthplace of improv, Chicago is known for its groundbreaking comedy clubs like The Second City.
• Explore more than 200 storefront theatres, offering classic, unconventional, and innovative productions all over Chicago.
• Discover Chicago’s dance scene, with stunning venues and renowned companies like the famed Joffrey Ballet.

Tip: For Chicago-style theatre at discounted prices, plan your trip for the city’s annual Chicago Theatre Week in February. And grab half-priced tickets from Hot Tix all year round.

Take a bite of our acclaimed dining scene

Chicago’s dining scene is a reflection of the city itself — diverse, dynamic, and full of hustle and heart. Taste iconic only-in-Chicago dishes, dine at bucket-list restaurants, attend a top food festival, and explore the international options in our global neighborhood. Just make sure to come hungry.

First-time visitors guide to Chicago dining:

• Experience award-winning fine dining at the city’s James Beard Award winners and Michelin-rated restaurants.
• Take a bite out of classic Chicago dishes like deep dish pizza, the Original Rainbow Cone, the jibarito, and more.
• Dine with a view at rooftop bars or lakefront restaurants.
• Travel the world without leaving Chicago at our international dining options.
• Eat like a local in our foodie neighborhoods, from trendy spots to under-the-radar enclaves.

Mark your calendar for the city’s biggest food and drink events, including Chicago Restaurant Week in January and February, the James Beard Awards in the spring, Taste of Chicago in summer, and Chicago Gourmet in September.

Tip: Chicago’s many unique food tours are a great way to try a lot in a short amount of time. Walk in the foot steps of “The Bear” cast, sample the city’s best pizza slices, or eat your way through Chinatown.

Root for the home team

Chicago’s many sports teams are truly the stuff of legends. This is the city of record breakers and curse shakers, where iconic athletes like Michael Jordan have changed the game forever. Come feel the exhilarating energy of Chicago’s sports scene.

First-time visitors guide to Chicago sports:

• The Chicago Cubs and White Sox (MLB) inspire a heated rivalry among locals. In the off season, book a tour of historic Wrigley Field.
• Two of the city’s most famous teams, the Chicago Bulls (NBA) and Blackhawks (NHL), play at the United Center (known as “The Madhouse on Madison”).
• Fans flock to Wintrust Arena to cheer on the Chicago Sky (WNBA).
• Chicago’s historic Soldier Field overflows with game-day energy when the Chicago Bears (NFL) or the Chicago Fire (MLS) take the field.

For an interactive look at Chicago sports history, the Chicago Sports Museum is filled with memorabilia, hands-on challenges, and more.

Chicago resources for first-time visitors

Start planning your first visit to Chicago with our resources for travelers from near and far.

• Our guide for international visitors to Chicago offers tips for smooth entry into the United States.
• Find out how to navigate public transportation in Chicago, including our easy-to-use ‘L’ system.
• Learn more about accessibility in Chicago, from navigating public transit to sensory-friendly amenities.
• Explore the city with a friendly local as your guide with Chicago Greeter walks.
• Find your best time to visit Chicago, decide where to stay, then book your hotel.
• Our Chicago Visitors Guide offers trip inspiration, planning resources, an events calendar, and more.