Planning a trip to the Windy City? From the shore to the sky, there’s so much to do in Chicago! It truly has something for everyone – you can find museums, family-friendly activities, photo ops, romantic spots, and so much more! Explore Chicago’s iconic spots and must-dos below!
Updated March 2024
ICONIC SPOTS
Cloud Gate aka “The Bean”
Known to most as “The Bean”, Cloud Gate is Chicago’s most famous sculpture! Find it in Millennium Park Downtown, standing at 33-feet-tall. Pack your camera and take some pics of your reflection – a trip to Chi town isn’t complete without them! (Pictured)
Navy Pier
Stroll along the 3,300-foot-long pier on the shoreline of Lake Michigan for sunshine, amazing views of the city, and fun for all ages! Ride rides like a carousel and ferris wheel, shop for souvenirs, enjoy classic local bites, enjoy live music or hop on a cruise on the lake. During the summer, you can even catch nightly fireworks at 10pm!
Magnificent Mile
Shop ‘til you drop along Michigan Avenue! This massive stretch of shops is home to over 450 stores, including several flagship stores and upscale designers. If you work up an appetite while shopping, grab a bite at any of the 275 restaurants along the street!
Lake Michigan
Head to the beautiful (and massive) Lake Michigan to get on the water! There are tons of spots to take a dip, or you can hop on a boat tour. There are dozens of different boat companies, ranging in what you’re interested in. Take a romantic dinner or boozy brunch cruise with Spirit of Chicago or Odyssey Lake Michigan, get your adrenaline pumping on a high speed thrill ride with Seadog Cruises, or go back in time on a Tall Ship Windy sailboat ride!
Millenium Park
You probably know this public park for The Bean, but it has so much more to explore! It’s beautiful year round, featuring gorgeous gardens, educational exhibits, and art from each of the city’s 77 neighborhoods!
The Chicago Theatre
One of the most iconic places in Chicago, and one of the most well known venues in the United States, the Chicago Theatre has been a destination for locals and visitors since 1921. Find the iconic marquee sign and head inside to check out the beautiful architecture on a tour, or spend the night there for a show! Many entertainment legends have taken the stage here over the years, and today you’ll find a variety of acts ranging from music to comedy.
Wrigley Field
Go, Cubs, go! Wrigley Field is home to the beloved Chicago Cubs, and has been for over a century. If you’re visiting during baseball season, catch a game to cheer on the cubbies and enjoy a ballpark hot dog. If you’re there in the offseason, don’t worry! Year-round, you can take a tour of the ballpark, learn about the history, and even walk on the field. We highly recommend exploring the surrounding Wrigleyville neighborhood while you’re there!
FOR THE VIEWS
Chicago Electric Boat Company
This may be one of the most romantic ways to spend an afternoon in Chicago! With Chicago Electric Boat Company, you can rent an adorable 16-foot retro boat from the 1950s to ‘60s and cruise along the river. The boats are easy to drive, and BYOB, making it the perfect date and a unique way to see the city! In addition to the retro boats, you can also rent larger boats for groups. (Featured header image)
Chicago Riverwalk
One of the best free things to do in Chicago is wander along the riverwalk! The 1.25-mile-long pathway is lined with patio restaurants and bars, pop-up vendors, and public street art. Our favorite places to stop and relax are City Winery, O’Briens Riverwalk Café, and Tiny Tapp & Tiny Cafe, but you can also pack a picnic lunch to enjoy on the grass! (Pictured)
Montrose Beach
Just a quick drive up Lakeshore Drive, near Uptown, you’ll find Montrose Beach! There are dozens of beaches along Lake Michigan, but this is one of the largest, making it a fave for locals and visitors alike. Enjoy fun in the sun, paddleboarding, jet skis, sand volleyball, a bar and restaurant, and more. It’s also dog-friendly, so bring your pup!
North Avenue Beach
Near the Lincoln Park Zoo, North Avenue Beach is a great option for families! It features a massive beach house designed to look like a ship, multiple food vendors, water sports rentals, bikes, outdoor sports, and more. There’s truly something for everyone, and the amazing skyline views are worth seeing!
Skydeck
Head to the 103rd floor of the Willis Tower (formerly known as the Sears Tower), for amazing views of the city, and up to four states! The tower is the tallest building in Chicago, and the third largest in the Western Hemisphere, with views from 1,353 feet up. If you’re feeling brave, step onto the glass overhang – you’ll feel like you’re floating above the city streets!
360 Chicago
Step on the TILT thrill ride, which leans you at an angle on a glass window on the 94th floor of the John Hancock Building! The downward-facing views are incredible, and will definitely get your adrenaline pumping. If you need some liquid courage, check out the CloudBar which serves craft cocktails with a view!
MUSEUM & CULTURAL
Photo courtesy of the Field Museum
Adler Planetarium
Reach for the stars, literally! The Adler Planetarium was America’s first planetarium and will take you on the ultimate cosmic adventure. Stargaze your way through over a dozen exhibits, covering topics like the moon landing, our solar system, eclipses, astronomy in culture, and beyond. Definitely catch one of their mind-blowing Sky Shows under the dome!
American Writers Museum
Did you know Chicago produced famous writers like Ernest Hemingway and Shel Silverstein? The American Writers Museum in Chicago honors those and hundreds of other amazing writers from our country! You’ll find everything from word games to vintage typewriters, and a whole lot of learning. Whether you’re an avid reader, an aspiring author, or somewhere in between, this is an inspiring visit!
Art Institute of Chicago
A cultural gem in the heart of Downtown, the Art Institute of Chicago is a must-see for visitors! Explore over ten exhibitions, permanent and temporary, ranging from Van Gogh to Ancient Egypt. They’re open Thursday through Monday, so make your plans to visit on a weekend!
Chicago Architecture Center & Tours
Chicago is known for its unique architecture, which you can see all throughout the city! If you want to learn more about the historic variety of buildings Chicago has, you can explore it all at the 10,000-square-foot Architecture Center. You’ll find hundreds of scale models, interactive exhibits, and access to walking tours! Our favorite way to explore the architecture is through their riverboat tours, which you can purchase tickets for online!
Chicago Cultural Center
Immerse yourself in Chicagoan culture at one of the most beautiful buildings in the city, the Chicago Cultural Center! Great for all ages, the center is home to tons of free music, shows, films, lectures, art exhibitions, and more. You can also book a tour to learn about the 100-year-old building from an expert! Don’t miss the stained glass windows, they’re truly breathtaking.
Children’s Museum
This one’s for the kids! Located at Navy Pier, the Children’s Museum is full of fun for all ages, featuring exhibits like Circusville, dinosaur expedition, the cloud buster climbing space, and more. It’s the perfect place for kids to get creative, get moving, and learn!
Chinatown
Chi-town’s Chinatown will transport you across the globe! For over a hundred years, Chinatown has been home to amazing Asian eats, art, shopping, and more. Explore sites like the Chinese American Museum of Chicago, Nine Dragon Wall, and Ping Tom Memorial Park. No plans are needed here, you can truly just roam around Chinatown Square and take everything in. We recommend you take a water taxi over from Downtown, and come hungry!
Field Museum
Discover the natural wonders of the world at the famous Field Museum, located in Chicago’s Museum Campus on Lake Michigan. You’ll learn all about natural history plus how humans fit into it, from a variety of exhibits featuring ancient artifacts to scientific discoveries. Don’t forget to say hi to Sue, the famous T-rex skeleton on display! (Pictured)
Frank Lloyd Wright Buildings
In a city full of amazing architecture, it’s no surprise that Frank Lloyd Wright had some influence! The famous architect lived just outside of Chicago in Oak Park for 20 years of his career, and today you can check out his buildings and studio, scattered throughout the city. Check out the elegant Rookery Downtown, find the gorgeous Frederick C Robie House in Hyde Park, or head to Oak Park for an intimate tour of his studio and home, along with the historic Unity Temple!
Garfield Park Conservatory
Unwind in a natural oasis next to the bustling city! Garfield Park spans 184-acres to explore, featuring a swimming pool, landscape art, a fishing lagoon, athletic fields and tennis courts. It’s the third largest garden under glass in the world, which means you can visit year-round – even during the infamously cold Chicago winters!
Lincoln Park Zoo
Take a walk on the wild side at the beloved Lincoln Park Zoo, full of fascinating creatures from all over the world! The zoo is free to everyone and open 365 days a year, making it a go-to stop on a trip to Chicago. You’ll find over 200 species of animals, ranging from penguins to pythons, along with over 850 species of plants! It’s truly a beautiful place, and you can visit with peace of mind knowing they focus all their efforts on conservation.
Museum of Contemporary Art
One of the largest contemporary art museums in the world, this spot is the perfect place to spend an afternoon, especially if you’re escaping the cold weather! Explore modern works of multimedia art, rotating exhibitions, and more than 2,000 works. They even have weekly events like performances, book signings, and educational panels!
Shedd Aquarium
Dive into the aquatic world at one of the best aquariums in the US, with amazing marine protection efforts! You can find dozens of sea creatures here, like otters, stingrays, dolphins, jellyfish, penguins, fish….the list goes on. If you get the chance, definitely do the whale encounter, where you get to swim face-to-face with belugas! They also have tons of high-tech virtual reality and 4-D experiences.
The Warehouse
Music fans know – Chicago is house music’s home! That’s right, house music, which is now played all over the world, started at a warehouse in the 1970s. Known as The Warehouse, the building is an important part of the city’s Black and LGBTQ+ history. It was named a national landmark last year and recently restored, hosting monthly parties in honor of Frankie Knuckles, the DJ who started it all. It’s a quick visit, but worth a stop for music fans!
