Chicago Bucket List: 25 Best Things to Do in Chicago

Planning a trip to Chicago and wondering what to see and do? The city is packed with world-class museums, incredible food, lakefront views, and some of the most iconic architecture in the US.

Whether you’re visiting for a weekend or longer, you’ll find plenty of things to do in Chicago that make it one of the most exciting cities to explore.

From seeing The Bean in Millennium Park to taking an architecture boat tour, catching a Cubs game, or trying the city’s famous deep-dish pizza, there’s truly something for everyone.

In this guide, I’ve rounded up the best things to do in Chicago for first-time visitors, including top landmarks, local food spots, museums, and a few hidden gems you won’t want to miss.

Disclosure: This post contains a few affiliate links, which means I may receive a small commission, at no cost to you, if you make a purchase through my link.

Best Things to Do in Chicago You Can’t Miss

1. See Cloud Gate (The Bean) at Millennium Park

No trip to Chicago is complete without visiting Cloud Gate, better known as The Bean! This giant stainless steel sculpture has become one of the city’s most recognizable landmarks and a must-see for first-time visitors.

Designed by artist Anish Kapoor, it reflects Chicago’s skyline and the people walking beneath it, making it one of the best Instagram spots in Chicago.

The Bean sits in the heart of Millennium Park, which is part of the larger Grant Park area. It’s a lively spot surrounded by gardens, fountains, and public art, so it’s easy to spend an hour or two wandering around.

Try to visit early in the morning to enjoy it before the crowds arrive, or come back at night when the city lights reflect off the surface for a completely different view.

2. Admire the skyline from the Skydeck at Willis Tower

If you want the best panoramic view of Chicago, head up to the Skydeck at Willis Tower. Once known as the Sears Tower, this 110-story skyscraper is one of the tallest buildings in the Western Hemisphere and an essential stop on any Chicago itinerary.

The highlight is The Ledge, a series of glass boxes that extend more than four feet out from the building. Standing on the transparent floor with the city directly beneath your feet is both thrilling and a little nerve-wracking, but totally worth it for the view and photos!

Try to visit on a clear day for the best visibility, when you can see as far as four different states. Sunset is especially beautiful, as the skyline lights up and Lake Michigan glows in the distance.

Tickets often sell out, so it’s smart to book ahead online to secure your preferred time slot.

3. Visit the Art Institute of Chicago

The Art Institute of Chicago is one of the oldest and most impressive art museums in the United States, home to over 300,000 works spanning thousands of years. It’s a must for anyone who loves art, culture, or simply wants to experience one of the city’s most iconic institutions.

Inside, you’ll find everything from ancient sculptures and European masterpieces to contemporary photography and modern design.

Some of the most famous pieces include Grant Wood’s American Gothic, Georges Seurat’s A Sunday on La Grande Jatte, and works by Monet, Van Gogh, and Picasso.

Even if you’re not an art expert, the museum is easy to enjoy thanks to its beautifully curated exhibits and peaceful atmosphere.

Plan to spend at least a couple of hours here, and if you have extra time, grab a coffee at the museum’s café or take a stroll through the nearby gardens before continuing your day. For a more in-depth experience, you can also join a guided tour.

4. Stroll along the Chicago Riverwalk

One of the best things to do in Chicago is to take a walk along the Chicago Riverwalk. Stretching for about 1.25 miles through the heart of downtown, this scenic path follows the Chicago River and offers some of the city’s best views of its famous architecture.

The Riverwalk is lined with restaurants, bars, and public art, making it a great place to stop for lunch or a drink with a view. You can grab a coffee at Tiny Tapp, enjoy a glass of wine at City Winery, or simply sit along the water and people-watch as boats glide by.

It’s especially beautiful in the evening when the buildings light up and the reflections dance on the river. If you have extra time, you can even hop on a river cruise from one of the nearby docks to see the skyline from a different angle.

5. Take an architecture boat tour

Chicago is known for its incredible architecture, and there’s no better way to appreciate it than from the water.

An architecture boat tour takes you along the Chicago River while knowledgeable guides share stories about the city’s most famous buildings and the people who designed them.

You’ll pass landmarks like the Wrigley Building, Tribune Tower, and Marina City, along with dozens of skyscrapers that define Chicago’s skyline. The mix of classic and modern styles is fascinating, and the views are amazing for photos!

Most tours last around 75 minutes and depart several times a day from the Riverwalk area. It’s one of the most popular activities in the city, so try to book in advance, especially if you’re visiting during the summer or on a weekend.

6. Walk the Magnificent Mile

If you love shopping, sightseeing, or simply soaking in city vibes, don’t miss a walk along the Magnificent Mile.

This famous stretch of Michigan Avenue runs between the Chicago River and Oak Street, filled with flagship stores, luxury boutiques, and some of the city’s most beautiful architecture.

You’ll find everything from high-end brands and department stores to cafes, restaurants, and hotels. Even if you’re not in the mood to shop, it’s worth visiting for the atmosphere alone.

Landmarks like the Tribune Tower, the historic Water Tower, and the John Hancock Building all sit along this iconic avenue.

During the holidays, the Magnificent Mile is especially festive with lights and decorations, but it’s lively year-round. It’s a great area to stroll, grab a bite to eat, and get a feel for the energy of downtown Chicago.

7. Eat deep-dish pizza (Lou Malnati’s, Giordano’s, or Pequod’s)

Trying Chicago’s legendary deep-dish pizza is one of the most essential things to do in the city!

This isn’t your typical slice – it’s thick, cheesy, and baked in a deep pan with layers of dough, mozzarella, and chunky tomato sauce on top.

It’s hearty, messy, and completely worth it if you’re wondering what to do in Chicago for a true local food experience.

There’s an ongoing debate among locals about who makes it best. Lou Malnati’s, Giordano’s, and Pequod’s are three of the most popular spots, each with their own signature style.

Lou Malnati’s is known for its buttery crust, Giordano’s for its stuffed version, and Pequod’s for its caramelized cheese edges that crisp perfectly around the pan.

Deep-dish takes about 30 to 40 minutes to bake, so it’s the perfect excuse to relax with a drink and take a break from sightseeing before digging in.

8. Explore Navy Pier

Navy Pier is one of Chicago’s most famous attractions and a spot that definitely belongs on your Chicago bucket list.

Stretching more than half a mile into Lake Michigan, it’s packed with restaurants, shops, theaters, and rides, making it a fun stop for visitors of all ages.

The highlight is the Centennial Wheel, a 200-foot-tall Ferris wheel that offers incredible views of the city skyline and lakefront.

You’ll also find the Chicago Children’s Museum, the Crystal Gardens indoor botanical park, and plenty of seasonal events like fireworks in the summer.

If you’re visiting on a warm day, grab an ice cream and enjoy a walk along the pier, or come in the evening when everything lights up.

It’s touristy, but there’s something about the energy and the views that makes it a must on any trip to Chicago.

9. Join a Chicago food tour

If you’re a foodie, joining a Chicago food tour is one of the most fun and delicious ways to explore the city.

These tours take you to local favorites and iconic spots while sharing the stories behind Chicago’s most famous dishes. It’s the perfect mix of sightseeing and snacking your way through different neighborhoods.

Most tours include deep-dish pizza, Chicago-style hot dogs, Italian beef sandwiches, and a few surprise bites along the way. You’ll also get to see parts of the city you might otherwise miss, like the Loop or River North, depending on which route you choose.

It’s a great way to experience the city’s food culture without having to plan every stop yourself. If you’re looking for an easy and tasty way to tick off multiple items from your Chicago bucket list, this is it.

10. See Buckingham Fountain in Grant Park

Located in the middle of Grant Park, Buckingham Fountain is one of Chicago’s most beautiful landmarks and a classic stop for first-time visitors.

Built in 1927, the fountain was inspired by the Latona Fountain at the Palace of Versailles and represents Lake Michigan with its four seahorses symbolizing the neighboring states.

The fountain operates daily from spring through fall, with water shows running every hour. Each display lasts about 20 minutes, and in the evening, it lights up with colorful displays that make it even more photogenic.

It’s a peaceful place to relax and take in the skyline views after exploring Millennium Park or the nearby Museum Campus.

11. Visit 360 Chicago Observation Deck at the John Hancock Building

For another incredible view of the city, head to the 360 Chicago Observation Deck at the John Hancock Building. Located 1,000 feet above Michigan Avenue, it offers sweeping views of the skyline, Lake Michigan, and the shoreline stretching for miles in both directions.

One of the highlights here is TILT, a glass platform that gently tilts outward from the building, giving you a thrilling downward view of the city below. It’s not for the faint of heart, but it’s a fun experience and makes for some great photos.

There’s also a bar at the top where you can grab a drink while taking in the view. Try visiting close to sunset to watch the city light up, or go during the day for the clearest visibility.

Both offer incredible perspectives and make this one of the most memorable things to do in Chicago.

12. Visit Lurie Garden

Tucked right behind Millennium Park, Lurie Garden is one of downtown Chicago’s most peaceful green spaces and a great place to take a quick break from the city buzz.

The garden is known for its colorful mix of flowers and native plants that change beautifully with the seasons, from vibrant blooms in spring to golden tones in fall.

Designed to reflect Chicago’s motto, “Urbs in Horto,” meaning “City in a Garden,” it’s a lovely reminder of how much nature there is even in the middle of the city. The paths wind through tall grasses, wildflowers, and wooden walkways that make it feel like a hidden oasis surrounded by skyscrapers.

It’s free to visit, and since it’s right next to the Bean, you can easily stop by before or after seeing other nearby attractions.

13. Spend an afternoon at the Field Museum

The Field Museum is one of Chicago’s most famous museums and a must-visit for anyone interested in history, science, or world cultures. It’s massive, so plan to spend at least a few hours here exploring everything from dinosaur fossils to ancient artifacts.

One of the main highlights is Sue, the largest and most complete T. rex skeleton ever discovered. There’s also an incredible collection of Egyptian mummies, a detailed look at natural history, and interactive exhibits that are great for visitors of all ages.

Even if you’re not usually a museum person, the Field Museum is impressive enough to change your mind.

It’s located on the Museum Campus near the Shedd Aquarium and Adler Planetarium, so it’s easy to combine them into one sightseeing day.

14. Visit Shedd Aquarium

If you’re looking for one of the best things to do in Chicago, the Shedd Aquarium definitely deserves a spot on your list. It’s one of the largest and most impressive indoor aquariums in the world, home to over 30,000 animals from oceans, rivers, and reefs around the globe.

You can watch playful sea otters, spot penguins waddling along the ice, and see sharks, rays, and tropical fish gliding through massive tanks. The Caribbean Reef exhibit is one of the highlights, featuring a 90,000-gallon habitat right in the center of the building.

It’s a great stop for families and anyone who loves marine life, and since it’s part of the Museum Campus along with the Field Museum and Adler Planetarium, you can easily visit more than one attraction in the same day.

15. Explore the Museum of Science and Industry

Located in the Hyde Park neighborhood, the Museum of Science and Industry is one of Chicago’s most fascinating attractions and a favorite for both kids and adults.

It’s the largest science museum in the Western Hemisphere, filled with interactive exhibits that make learning feel anything but boring.

You can walk through a full-size replica of a coal mine, step inside a World War II German submarine, or explore a life-sized 727 airplane suspended from the ceiling.

There are also exhibits on space exploration, weather, and technology that change throughout the year, so there’s always something new to see.

The museum is huge, so plan at least half a day if you want to see the main highlights. Even if you’ve already visited some of the other big museums in Chicago, this one stands out for how immersive and hands-on it is.

16. Wander through Lincoln Park and visit Lincoln Park Zoo

Lincoln Park is one of Chicago’s prettiest neighborhoods and a great place to slow down after exploring downtown. The area is full of tree-lined paths, historic homes, and quiet green spaces, with skyline views peeking through the trees.

At the heart of it is Lincoln Park Zoo, one of the oldest zoos in the United States and one of the few that’s completely free to visit. It’s home to hundreds of animals, including lions, gorillas, and polar bears, and the enclosures are thoughtfully designed and easy to explore.

Before you leave, make sure to stop by the Honeycomb Pavilion in the South Pond area! This wooden structure frames one of the best skyline views in the city and is a favorite photo spot among both locals and visitors.

Between the zoo, the conservatory, and the park’s walking paths, Lincoln Park is a must-see part of any trip to Chicago.

17. Watch a Cubs game at Wrigley Field

Even if you’re not a big baseball fan, catching a game at Wrigley Field is one of the most iconic things to do in Chicago. Built in 1914, it’s one of the oldest ballparks in the country and home to the Chicago Cubs, one of the city’s most beloved teams.

The atmosphere on game day is electric, with fans filling the stands and nearby streets around Wrigleyville. You can grab a Chicago-style hot dog, cheer with the crowd, and soak up the local energy that makes this such a memorable experience.

If you’re visiting outside of baseball season, you can still tour the stadium to see the historic press box, dugout, and ivy-covered outfield walls. It’s a fun way to experience a true piece of Chicago history and culture, even if there’s no game happening.

18. Try a Chicago-style hot dog

You can’t visit Chicago without trying a proper Chicago-style hot dog!

This local favorite is made with an all-beef frank in a poppy-seed bun, then piled high with yellow mustard, chopped onions, relish, tomato slices, a dill pickle spear, sport peppers, and a sprinkle of celery salt. My mouth is watering even just thinking about it!

You’ll find great hot dogs all over the city, but a few of the most famous spots include Portillo’s, Superdawg Drive-In, and The Wieners Circle. Each place has its own personality, from classic diner vibes to cheeky late-night humor.

It’s the perfect quick bite between sightseeing stops and a fun way to experience one of Chicago’s true food traditions.

19. Enjoy the views from Adler Planetarium

The Adler Planetarium is known for its fascinating exhibits about space and astronomy, but one of the best reasons to visit is for the view.

It sits right on the edge of Lake Michigan on the Museum Campus, offering one of the most breathtaking skyline views in Chicago.

If you decide to go inside, the planetarium has immersive shows, hands-on exhibits, and plenty of interactive displays that are great for visitors of all ages. Whether you come for the skyline or the stars, it’s one of those places that deserves a spot on any Chicago bucket list.

20. Relax at North Avenue Beach

If you’re visiting Chicago during the warmer months, spending a few hours at North Avenue Beach is a must. Located in the Lincoln Park area, this stretch of sand has beautiful views of the city skyline and plenty of space to relax, swim, or rent a paddleboard.

It’s one of the most popular beaches in Chicago, especially on summer weekends when locals come out to soak up the sun. There are beach bars, volleyball courts, and a long path that connects to the Lakefront Trail, perfect for a scenic walk or bike ride.

The best part is the view. You can look out over Lake Michigan in one direction and see the skyline rising behind you in the other. It’s a great spot to take a break from sightseeing and enjoy a different side of the city.

21. Explore the West Loop and dine at Time Out Market

The West Loop has quickly become one of Chicago’s trendiest neighborhoods, packed with top-rated restaurants, stylish bars, and a mix of converted warehouses and modern lofts. It’s one of the best areas to stay in Chicago if you want great food, nightlife, and easy access to downtown.

Start your visit at Time Out Market, a huge food hall featuring some of Chicago’s best chefs and local favorites all under one roof. You can sample everything from tacos and sushi to gourmet burgers and handmade desserts, making it a great place to try multiple dishes in one stop.

After eating, wander along Randolph Street, often called Restaurant Row, where you’ll find even more amazing dining options and rooftop bars.

If you want a lively atmosphere, plan to come here for dinner and drinks. The neighborhood really comes alive at night and offers a completely different vibe from the tourist-heavy downtown area.

22. Visit Milton Lee Olive Park for sunset

If you’re looking for one of the best skyline viewpoints in the city, make sure to stop by Milton Lee Olive Park. Tucked between Navy Pier and Ohio Street Beach, this peaceful green space has a walking path that offers incredible views of both the Chicago skyline and Lake Michigan.

It’s especially beautiful at sunset, when the light reflects off the water and the city starts to glow. Many locals come here to run, walk their dogs, or simply sit and take in the view, but it never feels as crowded as some of the other downtown spots.

It’s also a great place for photos, especially if you want a clear, unobstructed skyline shot with the lake in the foreground.

Bring a snack or coffee, find a bench, and stay long enough to see the colors change across the water. It’s one of those quiet moments that makes you fall in love with Chicago all over again.

23. Go mural hunting around the city

Chicago has an incredible street art scene, and going mural hunting is one of the most fun and colorful things to do in Chicago.

It’s a great way to explore different neighborhoods while finding unique photo spots that showcase the city’s creative side.

One of the most famous murals is the Chicago Mural in the Wabash Arts Corridor, a massive artwork featuring the city’s name in bold, graphic letters.

You’ll also find tons of impressive pieces in Pilsen, known for its community murals, and Logan Square, which is full of bold, large-scale designs. Even downtown, you’ll spot unexpected art tucked between skyscrapers and under the El tracks.

If you love photography, spend a few hours walking around with your camera and discovering these colorful walls. It’s a relaxed and inspiring way to see a different side of the city.

24. Take photos at the Chicago Theatre sign

No trip to the city is complete without snapping a photo in front of the iconic Chicago Theatre sign! Located on North State Street in the Loop, this bright red marquee has been a symbol of the city since 1921 and remains one of the most recognizable landmarks in Chicago.

It’s a popular spot for both tourists and locals, so try to visit earlier in the day if you want to avoid crowds. The surrounding area is full of restaurants, shops, and classic architecture, so it’s easy to combine a quick photo stop with exploring the neighborhood.

If you have time, you can also catch a show inside the theater, which hosts concerts, comedy acts, and special events throughout the year. But even if you only stop for pictures, this spot definitely deserves a place on your list of things to do in Chicago.

25. Explore Chinatown

Chicago’s Chinatown is one of the most vibrant neighborhoods in the city and a great place to spend an afternoon trying new foods and soaking up the atmosphere.

The area is centered around Cermak and Wentworth Avenue, where you’ll find colorful architecture, shops selling traditional goods, and plenty of authentic restaurants.

Start your visit at the Chinatown Gate, then wander through the side streets to discover bakeries, bubble tea shops, and local favorites serving dim sum, noodles, and dumplings.

Lao Sze Chuan and MingHin Cuisine are two of the most popular spots, both known for their flavorful dishes and friendly service.

If you want a break from sightseeing downtown, Chinatown offers a completely different side of the city. It’s easy to reach by public transport, and it’s one of those neighborhoods that gives you a real taste of Chicago’s diversity.