View of the "Bean" in Millennium Park, one of the most popular things to do in Chicago

36 Best Things to Do in Chicago in 2023 (By a Local)

👉 Jump to: Best Things | Museums & Culture | Sites & Attractions | Outdoor Attractions | Food & Drink | Entertainment & Nightlife | FAQ

When it comes to things to do in Chicago, Illinois, this Midwestern destination is practically overflowing.

The city offers an incredible food scene, vibrant arts and culture, access to beautiful Lake Michigan, fantastic areas to stay, and is one of the best sports towns in America (and this is just for starters). At the end of the day, there’s something for everyone in Chicago.

No matter your reason for visiting, if you’ve never been to the Windy City then you’re in for a treat – Chicago has it all. I mean, after just one trip, I found myself packing up and moving here.

Let’s dive into the 36 best things to do in Chicago!

Disclosure: Travel Lemming is an independent reader-supported blog. You can support us by purchasing via the affiliate links on this page, which may earn us commissions. See our Advertising Policy for further explanation. Thank you!

36 Best Things to Do in Chicago

Explore Chicago’s Neighborhoods

Visit a few of Chicago’s many diverse and unique neighborhoods.

Exterior view of the historic home in Lincoln Park surrounded with greenery from across the street
Historic home in Lincoln Park

📍 18 Best Chicago Neighborhoods

You may have heard that Chicago is a city of neighborhoods. Although the boundaries and names of each neighborhood are a bit subjective, the city is distinctly made up of 77 community areas; each one with its own unique flair. 

If you’ve never been to Chicago, it can be tempting to spend all your time in the city’s downtown Loop. And while the Loop is an area worth spending time in for sightseeing, shake things up by exploring different neighborhoods in Chicago.

Head to Lincoln Park for a charming downtown feel. There are tons of shops to browse, and some of the best restaurants in Chicago to try. Plus, Lincoln Park (the actual park) and the zoo are nearby.

West Town is another great area to explore and has a great “local” vibe to it. Smaller neighborhoods like Wicker Park, Bucktown, and Ukrainian Village can all be found here.

Lastly, Gold Coast is a great neighborhood for some history and beautiful architecture. Take a walk through the area and admire the beautiful brownstone homes, which are only a short walk to the lake. 

Lakefront Trail

Run, walk, or bike along beautiful Lake Michigan on this 18-mile urban trail.

People enjoying the cityscape views from the Lakefront Trail
View of the city from the Lakefront Trail

📍 Google Maps | Phone: (312) 742-7529 | Lakefront Trail Website | Hours: Open 24 hours a day | Entrance: Free | 👉 Chicago Ultimate City Bike Tour

Part of what makes Chicago so unique is its access to Lake Michigan. In the winter, part of the lake freezes over and creates icy waves along the shore. In the summer, the lake provides a welcome escape from the heat. 

If you plan on visiting during the warmer months, set aside some time for the Lakefront Trail. This paved path runs for 18 miles along the city and shoreline, providing incredible views. The trail is free to everyone and perfect for walking, running, and biking.

Chicago Riverwalk

Take a leisurely stroll through the heart of Chicago.

Cityscape and bridge view from the riverwalk
The views from the Riverwalk are so pretty

📍 Google Maps | Phone: (877) 300-6746 | Chicago Riverwalk Website | Hours: 6 am – 11 pm daily | Entrance: Free

The Chicago Riverwalk is a 1.25-mile urban trail that lines the Chicago River just north of the Loop. This pedestrian path is one of my favorite ways to sightsee downtown. It’s free, open year-round, and lined with restaurants, bars, cafes, shops, and more. 

This is a great place to take a scenic, leisurely stroll, or sit down somewhere for a picnic or quick rest. You can access the Riverwalk via multiple entry points off of E Wacker Drive. Just head down to the river and find the signs marked “Chicago Riverwalk.”

👉 Did You Know? Every year for St. Patrick’s Day, the Chicago River is dyed green!

Millennium Park

Go sightseeing in Chicago’s downtown Loop.

View of the "Bean" in Millennium Park in Chicago
The famous ‘Bean’ sits in front of a beautiful city backdrop.

📍 Google Maps | Phone: (312) 742-1168 | Millennium Park Website | Hours: 6 am – 11 pm daily | Entrance: Free

Situated in the loop and housed within the larger Grant Park is Chicago’s Millennium Park. This park, which is also connected to Maggie Daley Park, is one of Chicago’s most iconic spots.

Here, you can enjoy activities and witness the city skyline up close. Most importantly, Millennium Park is home to Cloud Gate, or, as it’s better known, “The Bean.”

Millennium Park has a lot more to offer besides a picture with the Bean, though. All year round, you can walk the park, enjoy public art, and witness images at Crown Fountain – an interactive video sculpture. 

In the winter, you can go ice skating just below the Bean or at the nearby Maggie Daley ice skating ribbon.

In the summer, enjoy outdoor concerts and Chicago festivals. Favorites include the Chicago Blues Festival and Millennium Park Summer Music Series, which take place at Jay Pritzker Pavilion.

👉 Did You Know? Although Cloud Gate is stainless steel, artist Anish Kapoor drew inspiration from liquid mercury. The shiny, mirror-like surface was also meant to reflect the Chicago skyline. 

The Art Institute of Chicago

Enjoy a world-class collection of art in downtown Chicago.

Paintings and sculptures of different artists inside The Art Institute of Chicago
Each art gallery features different artists and styles from throughout history

📍 Google Maps | Phone: (312) 443-3600 | Art Institute Website | Hours: 11 am – 5 pm Fri – Mon, 11 am – 8 pm Thur, Closed Tue, Wed | Entrance: $25 for adults, $19 for seniors and students, Free for children

Located in the Loop and just south of Millennium Park is the Art Institute of Chicago. This world-class museum features thousands of artworks from around the world, spanning centuries and styles. Think of artists like Van Gogh, Monet, and Picasso, just to name a few. 

Plan to spend at least a few hours wandering the Art Institute. The historic building has four levels in total, with numerous wings and exhibitions to explore. The museum is also family-friendly. 

Do note that because of its size, young children and seniors may become tired. Tickets can be purchased online and in advance, but they may also be purchased on-site. 

👉 Pro Tip: I’ve found that one of the best ways to see and navigate a museum of this size is to start on the top floor and work your way down.  

Wrigley Field

Attend a baseball game at one of America’s most famous ballparks.

View of the iconic red marquee in Wrigley Field’s
Wrigley Field’s iconic red marquee

📍 Google Maps | Phone: (773) 404-2827 | Wrigley Field Website | Hours: On game days, gates open 2 hours before the first pitch | Tickets: Ranging from $10 – $300 

Chicagoans take their sports seriously, and this obviously includes Wrigley Field – home of the Chicago Cubs. Built in 1914 and located in the neighborhood of Wrigleyville, this famous stadium is the second oldest Major League baseball field in America. 

Throughout its history, the ballpark has witnessed so many historic moments, from Babe Ruth “calling his shot” in 1932, to “reversing the curse” in 2016. Not to mention, the Cubs have won three World Series titles and longstanding traditions are a key part of the experience.

The stadium itself has brick walls covered in ivy, as well as a beloved red marquee on display out front. As an ode to the beginnings of baseball, the scoreboard is manually operated, too.

Order some snacks or Chicago-style hot dogs if that’s your style. Although, to avoid some craziness, plan on getting lunch and drinks before your game.

🚗 How to Get There: Parking can be a nightmare so a better option is to use the CTA Red Line or rideshare options for transportation. Just note that the train will most likely still be packed and rideshares can get pricey around game time.

Take an Architecture Cruise

Journey through Chicago’s history and architecture and enjoy amazing downtown views.

View of the great architectural buildings from the cruise
Views from my architecture cruise

📍 Google Maps | Phone: (312) 222-9328 | Shoreline Sightseeing Website | Hours: departure times vary | Entrance: $50 adults, $27 children | 👉 Chicago Architecture River Cruise

For visitors of all ages and interests, an architecture cruise is one of the best things to do in Chicago. You can expect to sit back and relax while a guide talks you through Chicago history and the iconic buildings that line the Chicago River. 

What’s great about this type of tour is that you can take in the sights and snap pictures from the comfort of your seat. You’ll leave with a better understanding of the city, its history, architecture, and more. Tours last about an hour long.

Chicago Museums & Cultural Attractions

👉 Pro Tip: You can also bookmark our full list of the 20 best museums in Chicago.

Museum of Contemporary Art

Engage with contemporary art exhibits designed to make you think.

The author Lea Rose Allbaugh passing by the illuminated neon sign at the Museum of Contemporary Art Chicago (MCA Chicago)
Me in front of one of the rotating exhibits

📍 Google Maps | Phone: (312) 280-2660 | Museum of Contemporary Art Website | Hours: 10 am – 9 pm Tue, 10 am – 5 pm Wed – Sun, Closed Mon | Entrance: $15 for adults, $8 for students, teachers, and seniors, Free for ages 18 and under

Unlike the Art Institute of Chicago, the Museum of Contemporary Art (MCA) features constantly rotating exhibitions by contemporary artists of today. I’ve been to MCA many times, and enjoy different and thought-provoking exhibitions on every visit.

This museum is family-friendly, but students and adults may especially appreciate the more nuanced, and often heavier, subject matter. Still, there is artwork for everyone to enjoy. The museum also offers live performances, events, and programs for the community. Expect to spend around an hour to two hours here. 

Field Museum

Immerse yourself in some natural history.

People checking out “Sue” the famous T-Rex in Field Museum
“Sue” the famous T-Rex

📍 Google Maps | Phone: (312) 922-9410 | Field Museum Website | Hours: 9 am – 5 pm daily | Entrance: $18 – $27 for adults, $19 – $29 for children ages 3 – 11, Free for ages 2 and under

The Field Museum is located just south of Grant Park and is near the Shedd Aquarium and United Club Stadium. This massive museum is home to almost 40 million specimens and artifacts such as T-Rexes, meteorites, animal biology, and more.

This museum is especially family-friendly and aimed at immersing children in science and discovery. 3D movies are also shown for the whole family to learn from so plan to spend an entire morning or afternoon here. 

A visit to the Field Museum is a great way to experience natural wonders and history all in one afternoon.

👉 Want to Explore More Around Chicago? Bookmark my guide to the best day trips from Chicago.

Chicago Children’s Museum

Let your kids play, learn, and explore to their hearts’ content.

Exterior view of the Chicago Children’s Museum and the different flags above
Outside the Chicago Children’s Museum

📍 Google Maps | Phone: (312) 527-1000 | Chicago Children’s Museum Website | Hours: 10 am – 5 pm Fri – Sun, 10 am – 2 pm Mon & Thur, Closed Tue & Wed | Entrance: $19 for adults and children, Free for ages 1 and under

At the Chicago Children’s Museum, children of all ages can enjoy a space to play and learn. Located on Navy Pier, the museum itself is comprised of more than a dozen exhibits that cater to different interests and experiences.

For some math, science, and discovery, exhibits like Tinkering Lab, Skyline, and Dinosaur Expedition will allow children to tinker, build mini-skyscrapers, and even dig for dinosaur bones. At the Art Studio, children can let their imaginations soar with painting, drawing, and pottery-inspired workshops. 

Additionally, children can learn practical life skills and take the lead at exhibits like Kids Town and Michael’s Museum. And for some overall fun, there are tons of exhibits for your little ones to climb, play, explore, and learn. 

Chicago History Museum

Uncover Chicago’s history.

The Chicago History Museum building from the outside and the clear blue sky over it
The museum’s exterior features Chicago’s famous blue stripe, four star flag (photo: Thomas Barrat / Shutterstock)

📍 Google Maps | Phone: (312) 642-4600 | Chicago History Museum Website | Hours: 9:30 am – 4:30 pm Tue – Sat, 12 – 5 pm Sun, Closed Mon | Entrance: $19 for adults, $17 for students and seniors, Free for ages 18 and under (Illinois residents) 

Located right near the lake in the southeastern corner of Lincoln Park is the Chicago History Museum. One of Chicago’s oldest cultural institutions, a visit to this museum will walk you through the city’s historic past to learn about what makes Chicago, well, Chicago. 

Exhibitions explore topics like freedom, democracy, and the history of Abraham Lincoln. A film is also available to learn about the city’s growth and events like the Great Chicago Fire of 1871. There’s even an exhibit for uncovering the city through the five senses.

👉 Pro Tip: If you’re a first-time visitor, I recommend stopping at the Chicago History Museum early on in your trip and planning to spend a couple of hours here. This way, you’ll have a better idea of what you’re seeing as you explore the city. 

National Museum of Mexican Art

Appreciate Mexican art and culture.

View of Traditional Mexican dancing in Downton Pilsen
Traditional Mexican dancing in downtown Pilsen (photo: Roberto Galan / Shutterstock)

📍 Google Maps | Phone: (312) 738-1503 | Museum of Mexican Art Website | Hours: 10 am – 5 pm Tue – Sun | Entrance: Free

Located in the neighborhood of Pilsen, the National Museum of Mexican Art is home to one of the largest collections of Mexican art in the country. This museum, which first opened in 1987, features both permanent and rotating art exhibitions, as well as cultural performances, films, and programs. 

Although the museum may be especially appreciated by members of the Mexican community, it is open to visitors of all ages and backgrounds. Visiting this museum is a great way to learn, support, and appreciate Mexico’s rich history and vibrant artwork.

Chicago Cultural Center

Learn about a historical landmark and attend free public events.

View of the largest Tiffany stained-glass dome between the pillars in the Chicago Cultural Center
The largest Tiffany stained-glass dome between two pillars

📍 Google Maps | Phone: (312) 744-5000 | Chicago Cultural Center Website | Hours: 10 am – 5 pm daily | Entrance: Free

The Chicago Cultural Center is one of Chicago’s (and the nation’s) most comprehensive cultural centers. Built in 1897, this historic Chicago landmark serves as a cultural destination for the public. The building itself has two beautiful stained-glass domes and intricate architectural details throughout, making it an absolute marvel.

The center’s main focus is bringing free events for everyone to enjoy. This includes art performances and exhibitions, lectures, and cultural events. Guided tours are also available. 

If you’re interested in history, arts, and culture, then this is a good stop to make on your itinerary for Chicago.

👉 Did You Know? The building’s south dome is actually the largest stained-glass Tiffany dome in the world!

Take a Food Tour of Chicago

Eat and drink your way through Chicago’s incredible food scene.

View of the stretchy cheese from a Chicago deep dish pizza

📍 Chicago Food Authority Website | 👉 Book the Chicago Food Tour (“Deep Roots to Deep Dish”)

There’s no doubt that Chicago is a foodie’s playground. The food in Chicago is incredible. The city offers an abundance of international and specialty restaurants, as well as distinct Chicagoan staples.

Whether you’re looking to splurge on a luxury meal at a Michelin-star restaurant like Alinea, wanting to indulge in Chicago-style hot dogs and deep-dish pizza, or try a cuisine you’ve never tasted before, Chicago has you covered. 

To really experience Chicago’s food scene, I recommend booking a food tour like the popular “Deep Roots to Deep Dish” Chicago food tour.

You can also plan your Chicago trip during the city’s famous “Taste of Chicago” food festival (2023 dates are June 24th, July 15th, August 5th, September 8th-10th). No matter your taste, budget, or cuisine preference, Chicago’s food scene has something for everyone.  

👉 Pro Tip: For specific restaurant recommendations, scroll down to the “food” section of this article.

Chicago Sites & Attractions

Navy Pier

Enjoy a day of views, attractions, and fun for the whole family.

The author Lea Rose Allbaugh posing with the cityscape in the background at Navy Pier
Admiring the city views from Navy Pier

📍 Google Maps | Phone: (312) 595-7437 | Navy Pier Website | Hours: 11 am – 7 pm Sun, 11 am – 8 pm Mon – Thur, 11 am – 9 pm Fri – Sat | Entrance: Free (entry fees for attractions and rides may vary) | 👉 Fireworks Kayak Tour

Just north of the Loop in the Streeterville neighborhood, Navy Pier extends out into the Lake Michigan shoreline. This pier has activities and restaurants for the whole family to enjoy, and is also a great spot for snapping some pictures of the lake and Chicago skyline.

Some of the popular activities and attractions at the pier include: Cruise tours, Centennial ferris wheel, the Chicago Children’s Museum, Chicago Shakespeare Theater, and Navy Pier Beer Garden. There is also the Polk Bros Park, where you can rest, relax, or enjoy free events and programs. 

Navy Pier also offers seasonal attractions such as fireworks in the summer and Light Up The Lake in the winter (an indoor light garden).

📚 See our full Navy Pier guide to get planning.

Willis Tower Skydeck

Take in sweeping views of the city.

Overlooking view from Willis Tower Skydeck
View from the Skydeck (photo: Thomas Barrat / Shutterstock)

📍 Google Maps | Phone: (312) 875-9447 | Skydeck Website | Hours: 9 am – 8 pm Weekdays, 9 am – 10 pm Weekends | Entrance: $30 – $44 ages 12 and up, $22 – $36 ages 3 – 11, Free for ages 3 and under | 👉 Skydeck and Ledge Ticket

For breathtaking views of Chicago, head to Willis Tower in the Loop. Formerly known as Sears Tower, this 108-story building is the tallest building in all of Chicago and the second tallest building in North America.

The Willis Tower Skydeck and Ledge is located on the 103rd floor and is a family-friendly way to take in the city below. Upon entrance, you’ll weave through educational displays and exhibits designed to give you a taste of Chicago’s history. This is all leading up to the main Skydeck itself where you’ll see the city through floor-to-ceiling windows. 

If you’re not afraid of heights, step out on the Ledge. This 4.3 feet glass box extends out over the city for views in every which way – on a clear day you might be able to see four states!

👉 Pro Tip? Definitely take the weather into account when visiting Willis Tower. For the best views, visit on a clear day.

Lincoln Park Zoo

Come face to face with wildlife.

A gorilla roaming around the huge roots of the trees surrounded with greenery at the Regenstein Center for African Apes
A gorilla at the Regenstein Center for African Apes

📍 Google Maps | Phone: (312) 742-2000 | Lincoln Park Zoo Website | Hours: 10 am – 5 pm daily | Entrance: Free 

Get up close and personal with animals at Lincoln Park Zoo. This Chicago zoo, which is free to all, is located in the heart of Lincoln Park. Almost 200 species of animals from around the world can be found here — bears, crocodiles, hippos, and everything in between. 

Most habitats are designed for visitors to observe the animals in their own environment, but a few interactive opportunities are available, too. The zoo is fairly easy to navigate, so if you plan on seeing all the exhibits, plan on spending an entire afternoon here. 

👉 Pro Tip: Although the Lincoln Park Zoo is free, parking can range from $20-$35. If you want to avoid this cost, then I recommend taking public transportation to the nearest train or bus stop. Or, if your accommodations are nearby, take a walk through Lincoln Park and over to the zoo.  

Shedd Aquarium

Experience what’s under the surface.

View of the Lake Michigan from Shedd Aquarium
Views of Lake Michigan can be seen right outside of Shedd Aquarium (photo: S-F / Shutterstock)

📍 Google Maps | Phone: (312) 939-2438 | Shedd Aquarium Website | Hours: 9 am – 5 pm daily | Entrance: $20 – $40 for ages 12+, $15 – $30 for ages 3 – 11, Free for ages 3 and under 

In addition to the Lincoln Park Zoo, Chicago also has its own state-of-the-art aquarium. The family-friendly facility is located right on the water along Chicago Harbor. This 5-million-gallon aquarium houses aquatic life from around the world including animals native to the Great Lakes.

There is a wide variety of exhibits to explore during your visit. Popular options include the Abbott Oceanarium, Wild Reef, Caribbean Reef, and more. Children can even enjoy interactive experiences where they can touch Stingrays, Sea Stars, and Sturgeons. 

Shedd Aquarium is also near the Field Museum and Adler Planetarium, in case you want to plan a whole day around these attractions.

Adler Planetarium

Travel through space and time.

Exterior and entrance view of Adler Planetarium with a clear blue sky in the background
The entrance to Adler Planetarium

📍 Google Maps | Phone: (312) 922-7827 | Adler Planetarium Website | Hours: 9 am – 4 pm Fri – Mon, 4 pm – 10 pm Wed, Closed Tue & Thur | Entrance: $19 – $35 for adults, $8 – $24 for ages 3 – 11 

Take in the universe and learn all about astronomy at Adler Planetarium. This museum and historical landmark is located on Northerly Island at the base of Chicago Harbor. This is right near the Field Museum and Shedd Aquarium. 

Adler Planetarium is family-friendly and an interactive experience for everyone. Theater programs are shown every day and educational events happen throughout the year. Popular exhibits include Astronomy in Culture, Chicago’s Night Sky, Our Solar System, and more.  

👉 Did You Know? Adler Planetarium was the first planetarium in America!

360 Chicago Observation Deck

Take a tilt over Chicago.

People trying out Tilt in 360 Chicago
Tilt allows visitors to take in Chicago from a new perspective (photo: Alex Cimbal / Shutterstock)

📍 Google Maps | Phone: (888) 875-8439 | 360 Chicago Website | Hours: 9 am – 11 daily | Entrance: $30 – $50.50 for ages 12+, $20 – $35.50 for ages 3 – 11 

Looking to take in the Chicago skyline from a new perspective? At the 360 Chicago Observation Deck, you can do just that. 

From the 94th floor of the John Hancock Center, you’ll be met with 360-degree views of the city, lake, and surrounding areas. Because of the building’s location, you’ll have especially close views of the Magnificent Mile and Lake Shore Drive. 

For an extra wow factor, take a ride on Tilt. This attraction will tilt you more than 1000 feet over the Magnificent Mile on Michigan Avenue. If you have a fear of heights, then this might not be the experience for you. But for most visitors, regardless of age, this is a unique and thrilling experience.

👉 Pro Tip: Similar to Willis Tower, I recommend visiting the John Hancock Center on a clear day. You’ll get the most out of your money and witness the best views. 

Art on theMART

Watch this iconic architectural attraction light up with color and movement.

View of the colorful digital art projected on the exterior building
One of the best free things to do on a night out in Chicago 

📍 Google Maps | Phone: (800) 677-6278 | Art on theMART Website | Hours: 8:30 pm – 9 pm daily | Entrance: Free 

Art on theMART is the largest digital art projection in the world. It runs every night between the months of April and December. Art collections rotate throughout the year, so there’s always a new light show to see. 

I recommend making a whole evening out of Art on theMART. Grab dinner on the river beforehand, and then find a spot to sit or stand on the Chicago Riverwalk across from the iconic building. Then, watch as thousands of light projections cast colorful, moving artworks on the facade of theMART. It’s a truly unique experience!

Magnificent Mile

Shop your heart out and take in the sights.

View of skyscrapers in Magnificent Mile Chicago
Where the end of the Magnificent Mile meets the Chicago River

📍 Google Maps | Phone: (312) 642-3570 | Magnificent Mile Website | Hours: Open daily, shop hours may vary | Entrance: Free

If you’re looking to do some luxury shopping and hit up those big-name stores, then pay a visit to the Magnificent Mile. Technically named North Michigan Avenue, this mile-long stretch is packed with shops, restaurants, luxury hotels, and more. 

Although a bit touristy, it’s worth visiting for anyone with an itch to shop. Not to mention, it’s close to the lakefront and only a short walk to the Chicago River and River North neighborhood for some more shopping. 

While you browse the Magnificent Mile, be sure to take in some of the historic buildings along the way like the Chicago Water Tower, Tribune Tower, and Wrigley Building.

👉 Love History? If shopping isn’t your thing and you’d rather experience the Magnificent Mile from a historical point of view, check out this Magnificent Mile Walking Tour!

United Center

Watch Chicago basketball, hockey, and more.

The United Center building in Chicago
Famous Chicago sports venue (photo: Tomas Barrat / Shutterstock)

📍 Google Maps | Phone: (312) 455-4500 | United Center Website | Hours: Game and show times may vary, doors open 90 minutes prior to games | Entrance: Each event may vary 

On the Near West Side of Chicago is the city’s other famous sports venue: United Center. 

This indoor arena is home to the NBA’s Chicago Bulls and NHL’s Chicago Blackhawks. In addition to being a sports venue for basketball and hockey games, United Center serves as an arena for concerts and other shows – it’s also America’s largest arena.

A couple of cool things to see at the United Center include the 58 banners hanging from the ceiling (marking championship titles for both the Bulls and the Blackhawks) and the 12-foot tall bronze Michael Jordan statue.

🛏️ Need a Hotel? The Hyatt House Chicago Medical/University District has good amenities and is located close to the arena if you’re going to an event at United Center.

Outdoor Attractions in Chicago

Grant Park

Visit one of Chicago’s biggest cultural hubs.

View of sunset from the Grant Park in Chicago
Sunset views of the city from the middle of Grant Park

📍 Google Maps | Phone: (312) 742-3918 | Grant Park Website | Hours: 6 am – 11 pm daily | Entrance: Free 

Known as downtown Chicago’s “front lawn,” Grant Park is a cultural hub that spans over 300 acres. In many ways, it’s the central, go-to place for a nature escape downtown as it houses Millennium Park and Maggie Daley Park

This vast green space is more than just a park, though. Some of the best and most popular things to do in Chicago all converge in this one place.

Besides Cloud Gate and everything within Millennium and Maggie Daley Parks, the Chicago Art Institute, Lakefront Trail, and Buckingham Fountain can all be found here.

And throughout the year, Grant Park also hosts a plethora of Chicago festivals including Taste of Chicago, SummerDance, and most notably, Lollapalooza.

North Avenue Beach

Spend an afternoon on Lake Michigan.

People enjoying their day during summer in North Avenue Beach
The perfect place to cool down in the summer

📍 Google Maps | Phone: (312) 742-5121 | North Avenue Beach Website | Hours: 11 am – 7 pm daily | Entrance: Free 

If you plan on visiting in the summer, then spending some beach time in Lake Michigan is one of the best things to do in Chicago. For an afternoon by the water, I recommend North Avenue Beach. 

Though it can get a bit crowded on hot days, this Chicago beach is close to downtown and falls along the Lakefront Trail. Volleyball courts and water sports rentals are available here.

North Avenue Beach also features incredible views of the city and lake. Walk out on the boardwalk to take in the picturesque Chicago skyline and bright blue water. Just note that it can get pretty windy out on the boardwalk. It is the Windy City after all. 

🚗 Need some wheels? Though getting around Chicago is easily done with the transit system, I recommend renting a car with Discover Cars if you plan on venturing out of the main parts of Chicago.

Kayak the Chicago River

Paddle down the Chicago River and take in the city from a new perspective.

View of tourists kayaking near downtown in Chicago River
Kayaking downtown

📍 Google Maps | Phone: (312) 965-0035 | Urban Kayaks Website | Hours: departure times vary | Entrance: $70 single kayak, $140 tandem kayak | 👉 Riverwalk Kayak Tours

If you plan on visiting during the warmer months, try something a little different: kayak down the Chicago River! This is a fun activity for visitors of all ages and a unique way to experience the downtown scene. 

This historic Chicago kayak tour is a particularly popular one, where you get a history tour while you paddle along the urban landscape. Tours typically last about two hours and are beginner-friendly. 

Bloomingdale Trail “The 606”

Take a walk along Chicago’s urban greenway.

View of the bridge from the trail surrounded with greenery
The 606 at Milwaukee access point

📍 Google Maps | Phone: (312) 742-4622 | 606 Website | Hours: 6 am – 11 pm daily | Entrance: Free

The Bloomingdale Trail, better known as “The 606,” is a 2.7 mile-long walking trail that extends west from Ridgeway Ave, and then east to Ashland Ave.

This trail, which was transformed from an old rail line, offers a refreshing outdoor escape and is perfect for runners, bikers, and anyone who wants to enjoy a nice stroll. 

There are 12 entry points to reach the trail from. Depending on where you stay in Chicago, the easiest way to reach the 606 is by taking the CTA Blue Line. Damen and Western stops will bring you within walking distance of the trail itself. 

If you’re looking to get a little exercise in while still enjoying the city, head to the 606!

Garfield Park Conservatory

Experience a natural oasis just outside the city.

View from the inside of Palm House in Garfield Park Conservatory
Inside of the Palm House (photo: Thomas Barrat / Shutterstock)

📍 Google Maps | Phone: (773) 638-1766 | Garfield Park Conservatory Website | Hours: 10 am – 8 pm Wed, 10 am – 5 pm Thur – Sun, Closed Mon – Tue | Entrance: Free, but online reservation required

Garfield Park Conservatory in Garfield Park is located about halfway between downtown Chicago and Oak Park. This conservatory, which is one of the largest in the country, is a beautiful place to witness nature and plants from around the world. In total, the conservatory has 2 acres of greenhouse space and 10 acres of garden.

Plan on spending around one to three hours wandering this nature oasis. Popular garden collections include the Palm House, Desert House, and Fern House. The conservatory also offers exhibit and installation events, and educational programs. 

Overall, the Garfield Park Conservatory is the perfect nature escape from Chicago. 

Food & Drink in Chicago

Lou Malnati’s Pizzeria

Pizza the Chicagoan way.

A woman's hand taking a slice of Chicago-style Pizza
Indulge in this Chicago classic

📍 Google Maps | Phone: (312) 828-9800 | Lou Malnati’s Website | Hours: 11 am – 11 pm Sun – Thur, 11 am – 12 am Fri, Sat

When it comes to food, deep-dish pizza is a distinctly Chicagoan thing. This style of pizza is sometimes referred to as “Chicago-style pizza” and is made with a thick crust, and stacked with layers of sauce, cheese, and toppings. The layers are even placed on the dough backward, with cheese placed first and sauce topped off last. 

If you’re looking to taste a classic deep dish, then head to Lou Malnati’s. They have multiple locations and are one of the oldest deep-dish pizzerias in Chicago. Their pizzas are known for their made-from-scratch, flaky, buttery crusts, and fresh ingredients. 

This is a great option that’s both casual and family-friendly.

👉 Pro Tip: Deep dish pizza can take a while to bake, so plan for a little extra time. 


Fresh flavors and comforting food.

View of pasta with cherry tomatoes and burrata with drinks in Etta
I had the pasta with cherry tomatoes and burrata–it had one of the best sauces I’ve tasted

📍 Google Maps | Phone: (312) 766-4444 | Etta Website | Hours: 12 pm – 10 pm Weekdays, 10:30 am – 10 pm Weekends

If you’re looking to enjoy a nice sit-down meal with delicious food, then you can’t go wrong with a meal at Etta. This restaurant, which has locations in River North and Bucktown, offers farm-to-table style cuisine.

You can expect fresh, seasonal ingredients, pasta, wood-fired pizzas, and focaccia. They also have a flavorful selection of cocktails. 

Overall, the atmosphere at Etta is warm and inviting. I’ve always enjoyed my food and drinks each time I’ve been here, and it’s a great choice for a semi-formal dinner with friends and family. Like many restaurants in Chicago, I recommend making reservations ahead of time.


A bakery and restaurant with modern Filipino cuisine.

Closeup view of the Filipino style spring rolls with ketchup and a plate of fried rice in the background
Lumpia–Filipino-style spring rolls

📍 Google Maps | Phone: (773) 697-3790 | Kasama Website | Hours: 9 am – 3 pm Wed – Sun, Closed Mon, Tue

On a quaint street in the West Loop’s Ukrainian Village is Kasama – a modern Filipino restaurant and bakery. Whether you’re familiar with Filipino food or not, this restaurant is worth visiting.

Since its opening in the summer of 2020, Kasama has been a hit – receiving dozens of awards for “best new restaurant” in Chicago and throughout the U.S.

The restaurant offers a unique combination, too: Filipino classics (for example: lumpia, adobo with garlic rice, etc.) as well as French bakery items with a Filipino twist. A wide variety of unique lattes, teas, and cocktails, are also available. 

As someone who grew up eating Filipino cuisine, I can tell you that the food at Kasama is delicious.

👉 Pro Tip: Different times of day are designated for breakfast and lunch, pastry and coffee takeout, and the fine dining tasting menu. Be sure to check their website hours for specific details. 

Time Out Market

Options for everyone to enjoy.

Huge signage with sushi inside the Time Out Market
Inside Time Out Market

📍 Google Maps | Phone: (312) 637-3888 | Time Out Market Website | Hours: 8 am – 10 pm Weekdays, 9 am – 10 pm Sat, 9 am – 9 pm Sun

Time Out Market is a food hall located in the Fulton Market District in West Loop. Here, some of the best restaurants, bars, and bakeries from around Chicago have vendor stalls all “under one roof.” Not to mention, the different selection of vendors means a wide array of cuisine options.

If you’re traveling in a group, then this is a great option to satisfy different taste buds. Everyone can order something unique but still enjoy a great meal together. No reservations are needed, but depending on what time you eat here, you may have to scour around for some seats. 

If you’re interested, the upstairs level of the building serves as an event space with a steady lineup of guests and programs. 

👉 Pro Tip: To get good seating on a busy day, have someone in your group secure some spots, and then take turns ordering. 

Chicago Entertainment & Nightlife

The Second City

Laugh your heart out at one of Chicago’s best comedy clubs.

View of the people settling down in front of the stage in The Second City
Right before a show

📍 Google Maps | Phone: (312) 337-3992 | Second City Website | Hours: 9 am – 10 pm Mon – Thur, 9 am – 12 am Fri, 10 am – 12 am Sat, 10 am – 10 pm Sun | Entrance: $25+ 

Second City comedy club in Old Town, Chicago has a long history and influence that’s made waves throughout the comedy world. Famous comedians like Joan Rivers, Bill Murray, Mike Meyers, Tina Fey, Amy Poehler, and so many others have performed and debuted here.   

If you’re someone who enjoys going out to shows (and frankly, just having a good time), snag a ticket to Second City. Shows can range from sketches and improv to stand-up and open mic nights. 

A kitchen and bar is also available at the venue. As far as things to do in Chicago, a comedy show at Second City is sure to be memorable. After all, they say laughter is the best medicine.   

👉 Pro Tip: The Second City does have an age requirement. Only those 13+ will be admitted, although ages 13-17 will need adult accompaniment.  

Chicago Theatre District

Witness world-class theatre and music concerts in downtown Chicago.

Cars passing along the Chicago Theatre District at night
The famous Chicago Theatre marquee glitters red and gold

📍 Google Maps | Theatre District Website | Hours: Showtimes may vary | Entrance: $25+

In the northern part of the Loop is the Chicago Theatre District. Here, you’ll find a wide array of theatres and performance venues. One of the major ones? The Chicago Theatre. This theatre, which primarily serves as a music and comedy venue, is widely known for its iconic red and gold marquee sign. 

A few other big theatres in the district include CIBC Theatre, James M. Nederlander Theatre, and Cadillac Palace Theatre. Each of these venues offers exciting Broadway and non-Broadway productions. Either way, Chicago holds its own when it comes to a flourishing theatrical scene. 

👉 Looking for shows? For a more comprehensive list of theatres and independent venues, check out the website link above. 

Buddy Guy’s Legends

Step into the heart of Chicago blues.

Buddy Guy performing with his guitar in Chicago
Buddy Guy doing what he does best – perform (photo: Sterling Munksgard / Shutterstock)

📍 Google Maps | Phone: (312) 427-1190 | Buddy Guy’s Legends Website | Hours: 5 pm – 1 am Wed – Sun, Closed Mon, Tue | Entrance: $15+ each show may vary

If you’re a fan of classic American blues, then visiting Buddy Guy’s famous Legends Blues Club is a must. Since its opening by Buddy Guy in the summer of 1989, this music venue has become a Chicago music institution and is one of the world’s premier blues clubs. 

The Legends’ stage has been played by iconic musicians like the Rolling Stones, Eric Clapton, David Bowie, John Mayer, and more. If you’re at all interested in music and Chicago’s music history, then attending a show here is sure to be a Chicago highlight. 

Who knows, you might be lucky and get a surprise performance from Buddy Guy.  

Symphony Center

Listen to one of the best orchestras in the world.

Exterior view of the Symphony Center from across the street
Entrance to the Symphony Center

📍 Google Maps | Phone: (312) 294-3000 | Chicago Symphony Orchestra Website | Hours: Show times may vary | Entrance: Ranging from $30 – $300 

The Symphony Center is located in the heart of the Loop and is a great itinerary addition if you’re a classical music lover.

The Chicago Symphony Orchestra, which is world-renowned, performs here throughout the year in a range of styles. You can expect classical performances as well as contemporary ones. 

The Symphony Center also offers music series to engage younger audiences. Kid-friendly programs are available as well as movie-inspired musical performances. In addition, the Symphony Center welcomes pianists, jazz artists, and performers of world and folk music.

FAQs About What to Do in Chicago

Is Chicago a good place to visit right now?

Chicago is a great place to visit right now, regardless of the time of year. Depending on what time of year you plan on visiting, activities may vary. Spring and fall are popular seasons to visit. Summer is also popular, but the city can get extremely hot. In contrast, winters can be extremely cold.

What is the number 1 attraction in Chicago?

Millennium Park, which houses Cloud Gate, is consistently ranked as one of the top attractions in Chicago. Although Millennium Park is worth visiting, there are a ton of other things to do and ways to explore the city.

Is Chicago worth visiting?

Chicago is worth visiting as it offers a wide variety of activities and attractions to choose from. The people are friendly, the city, parks, and lake create a unique experience, and there is always something to do. 

What is Chicago famous for?

Chicago is famous for sports, music, the food scene (including deep-dish pizza), architecture, and so much more.

What are some free things to do in Chicago?

Millennium Park, the Lincoln Park Zoo, the Lakefront Trail, and the Chicago Cultural Center are just a few of the many free things to do in Chicago.

What are the best things to do in Chicago?

The best things to do in Chicago include hitting up top attractions like Cloud Gate in Millennium Park, visiting the Art Institute of Chicago, and taking an architecture cruise. Exploring Chicago’s neighborhoods and enjoying the waterfronts at places like North Avenue Beach and the Lakefront Trail are great ways to experience the more local side of Chicago.


Now you know what to do in Chicago! I hope you enjoyed my list of the best things to do in Chicago! The Windy City has so much to offer, and I really believe there’s something for everyone.

Before you go, be sure to check out some of our other guides to the Midwest, like our ultimate guide to Minneapolis!

How useful was this post?

Click on a star to rate (you can leave feedback after clicking submit)

Help us help you travel better!

Your feedback really helps ...

What did you like about this post? Or how can we improve it to help you travel better?

One Comment

  1. How can you write about Millennium Park and music festivals without mentioning the Grant Park Music Festival at Pritzker Pavilion? 10 weeks, 30 concerts, absolutely free as it has been for over 85 years. With an orchestra that rivals the CSO and the finest chorus in the country, it is The Sound of Summer in Chicago. It also takes its show on the road to various Chicago Park District sites throughout the season.

Leave a Reply

All comments are moderated for compliance with our community guidelines. Most importantly be kind & be helpful!

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.