47 Best Things To Do in Chicago You Can’t Miss

Pack your bags, it’s time to head to the most populous Midwestern city — Chicago, Illinois!

The Windy City is full of fun things to do. Whether you’re a first-timer, traveling during warm weather, looking for kid-friendly activities, or are all about the nightlife — Chicago has it all. With amazing museums, art galleries, parks, a zoo, theaters, and amazing restaurants, you’ll never run out of things to do in Chi-Town.

Ready to get planning? Grab a slice of deep-dish pizza, here are 47 things to do in Chicago that you’re not going to want to miss!




The Art Institute of Chicago is one of the top museums in the world. Located within the famous Grant Park, the Art Institute is known for housing a vast collection of Impressionist and Post-Impressionist art, as well as an impressive collection of 20th-century photography. I used to live across the street from the museum, and I have to say that it is continually mind-blowing.

There are so many paintings and sculptures to see at the Art Institute of Chicago that it’s impossible to take it all in during one visit. I highly recommend spending at least a full day here if you can. And if you’re a fan of art, you owe it to yourself to visit this museum at least once in your lifetime. Trust me, it’s worth it.


If you’re looking for a museum that captures the essence of both natural history and cultural heritage, then the Field Museum in Chicago is your go-to destination. Here, you can learn all about the incredible diversity of our planet through wondrous displays and exhibits. Whether it’s dinosaurs or ancient cultures, this museum has it all.

Plus, it’s home to the beloved and incredibly well-preserved T-Rex, Sue. My personal favorite exhibit is the elaborate Egyptian collection. 

Whether you’re a seasoned traveler or just planning your first-ever trip, the Field Museum is definitely worth checking out.


Millennium Park is a world-famous tourist destination in downtown Chicago. The park features beautiful gardens, an iconic fountain, and some of the city’s most popular attractions. Visitors can enjoy stunning views of the skyline, take a stroll through the gardens, or explore the many shops and restaurants in the area. If you’re visiting in the summer, be sure to catch a free summer concert under the Pritzker Pavilion. 

Grab your camera, and get your picture in front of  one of the world’s largest permanent outdoor art installations — The Bean, officially named Cloud Gate. This cool sculpture has been here since 2004, and is now one of the most iconic sites in Chicago.

Millennium Park is a great place for both locals and tourists alike.


The Shedd Aquarium is a world-renowned facility located in downtown Chicago. Visitors can view over 32,000 animals from all over the world, including sharks, penguins, and dolphins.

The Shedd also offers many educational opportunities, such as behind-the-scenes tours and animal encounters.


The Museum of Science and Industry is absolutely massive, featuring tons of exhibits and collections that are guaranteed to fascinate people of all ages. The museum has a strong focus on science and engineering, with many interactive displays that allow visitors to learn about everything from nanotechnology to astronomy, in a fun and engaging way.

Additionally, the museum highlights science that played an important role in history, such as the development of the assembly line during the Industrial Revolution.

One of my favorite things to do when visiting is to explore the full-size Boeing 727 and a WWII German U-Boat.

You’ll find the Museum of Science and Industry on the east side of the culturally-rich Hyde Park neighborhood, home to the 1893 World’s Fair.


Located on the 103rd floor of the iconic Willis Tower, Skydeck Chicago offers some of the best views of the city from above. With sweeping panoramic vistas that allow you to take in all aspects of this bustling metropolis, this popular attraction is a must for any visitor seeking a bird’s eye view of Chicago. On a clear day, you can see up to 50 miles away in any direction, making for some genuinely breathtaking photo opportunities.

If you’re a thrill-seeker, you can visit the 94th floor of the John Hancock building and experience 360 Chicago’s adrenaline-rushing experience called TILT. Visitors will hold on as a panel of glass tilts them forward, over 1,000 feet in the air. Whichever option you choose, you’ll be rewarded with stellar Chicago views.

Looking for online tickets to attractions or cool tours offering insider info? Get Your Guide is our family’s go-to resource for online purchases. Find 360 Chicago Observation Deck Skip-the-Line tickets here.


The Pullman Foundation Visitor Center is a starting point for your visit to the Pullman district. Visitors can enjoy a 15-minute video on the neighborhood’s history, and explore exhibits that feature historical photos, furniture, and artifacts from the Pullman mansion. 

The South Side of Chicago was originally a working-class neighborhood that was home to many African American residents and immigrants from Europe. In recent years, the South Side has undergone significant revitalization efforts, including the establishment of the Pullman Historic District in Chicago’s South Side.

Today, this vibrant district is a popular tourist destination, offering visitors a glimpse into the area’s history, as well as its thriving community of artists, entrepreneurs, and activists. Whether you are looking for a unique place to stay during your visit or simply want to learn more about South Side’s history and culture, the Pullman Foundation Visitor Center is an excellent resource.


The Magnificent Mile boasts everything from world-class shopping to fine dining.

There are numerous shops along the mile, ranging from major department stores, like Nordstrom and Bloomingdale’s, to smaller local boutiques and specialty stores.

If you’re heading to the Magnificent Mile with family or friends, there are also several attractions to enjoy, including museums, parks, and world-class theaters.


The Chicago Theater is a beautiful and historic theater located in downtown Chicago. I highly recommend stopping by this iconic landmark to experience its stunning architecture and enjoy a show or concert if you’re visiting the city. I’ve seen everyone from Carol Burnett to John Mulaney at this legendary theater.

You can also take a guided tour of the theater, where you will see a wall signed by every person who has ever performed there. This includes icons like Aretha Franklin and Duke Ellington.


The Garfield Park Conservatory is one of the most beautiful places in Chicago. It’s a vast, Victorian-style glass house filled with all kinds of plants from around the world. And it’s free to visit!

In addition, the Conservatory often hosts events, like concerts under the stars and yoga. 


The Chicago Cultural Center is one of the most visited attractions in Chicago, drawing hundreds of thousands of visitors to its stunning landmark building each year.

Home to two magnificent stained-glass domes and featuring free music, dance, theater events, films, and lectures, as well as art exhibitions and family programs, there is always something exciting happening at this iconic Chicago landmark.

Whether you’re looking for inspiration in a gallery, to attend a public event, or simply to sit and relax in the magnificent Grand Staircase–Escalante room, there is always something new to discover at the Chicago Cultural Center!


If you’re looking for a place to experience the ideas and work of living artists, check out the Museum of Contemporary Art in Chicago. This world-class museum is dedicated to showcasing new and experimental works of art in all media, as well as presenting thought-provoking educational programs.

 Today, the MCA’s collection features more than 2,000 works by artists from around the world. One of the exhibit’s most popular shows was “David Bowie Is,” which focused on Bowie’s extraordinary career.

Whether you’re a longtime fan of contemporary art or just getting started, a visit to the MCA is sure to inspire, educate, and delight.


I had the opportunity to visit Intuit, a premier museum of self-taught and outsider art in Chicago. This fascinating museum is dedicated to showcasing work created by artists who faced marginalization, overcame personal odds to make their artwork, or who did not, or sometimes could not, follow a traditional path of art-making.

With its diverse collection of outsider artwork, ranging from paintings and sculptures to musical instruments and other unexpected creations, Intuit provides a unique glimpse into the creative minds of these artists.

Whether you are an avid art lover or simply interested in exploring the world of outsider art, a visit to this museum is sure to delight and inspire.


47 Best Things To Do in Chicago You Can’t Miss


If you’re looking for a fun and unique way to see Chicago, then be sure to check out the Riverwalk. The Riverwalk is a 1.25-mile-long pedestrian path that runs along the bank of the Chicago River. It’s a great place to walk, run, or bike, and there are plenty of things to see and do along the way.

One of the best things about the Riverwalk is that it’s right in the heart of downtown Chicago. You’ll be able to see all of the city’s iconic skyscrapers up close, and you can even stop for a bite to eat or a drink at one of the many restaurants and cafes along the river.


Chicago is known for its beautiful parks and abundance of green space, and one of the most popular spots to see springtime blooms is the Garden of the Phoenix in Jackson Park.

Located just a few miles south of downtown Chicago, this lush garden is home to vibrant cherry blossom trees that are a sight to behold.


There’s something for everyone in Chicago’s Grant Park, from the world-famous Buckingham Fountain to the Museum Campus, home to three of the city’s most famous museums.

Visitors can tour Grant Park and see Buckingham Fountain, take a stroll through the beautiful gardens, or explore the many sculptures and monuments. The park also hosts a variety of events and festivals throughout the year, so there’s always something new to see. 


When relaxing at North Avenue Beach, you’ll quickly feel like you’ve been transported to the ocean.

There is always something happening at North Ave. Join a volleyball game, rent a paddleboard, or party at a beach club while taking in the stunning view of the Chicago skyline. The Lakefront Trail passes right through this area, so it’s a great stop to add to your biking itinerary!


Ping Tom Memorial Park is a beautiful park located in Chicago’s Chinatown neighborhood. The park honors the late Chinese-American entrepreneur and community leader, Ping Tom.

Visitors to the park can enjoy stunning views of the Chicago skyline, take a stroll through the tranquil gardens, or attend one of the many cultural events held here throughout the year.

Whether you’re looking for a place to relax and unwind or you want to experience the vibrant culture of Chicago’s Chinatown, Ping Tom Memorial Park is the perfect destination.


The Bloomingdale Trail is a must-do if you’re looking for a fun and relaxing way to explore Chicago. Affectionately known as the 606 (due to the Chicago zip code), this iconic walking and biking trail runs through some of the city’s most picturesque neighborhoods.

Whether you’re looking for a leisurely stroll or want to put your bike skills to the test, the 606 has something for everyone. Plus, there are many fantastic cafes just off the trail that are worth visiting. 


47 Best Things To Do in Chicago You Can’t Miss


Wrigley Field is the home of the Chicago Cubs, one of the city’s two Major League Baseball (MLB) franchises.

Wrigley Field Tours takes you through the iconic ballpark, providing an insider’s look at all the features that make it one of the most beloved stadiums in baseball. You’ll learn about the history of the team and the stadium, see the locker rooms and dugouts, and even get a chance to go onto the field itself.

Whether you’re a diehard Cubs fan or just interested in exploring one of Chicago’s most famous landmarks, a Wrigley Field Tour is a must-do activity.


Chicago is home to some of the most iconic architecture in the world. A boat tour offers the best way to see it all, with a leisurely architectural tour down the Chicago River.

Your expert guide will provide commentary on more than 40 famous buildings along the way, including Navy Pier, the Wrigley Building, and the John Hancock Center.

Looking for online tickets to attractions or cool tours offering insider info? Get Your Guide is our family’s go-to resource for online purchases. Find Guided Architecture Cruise tickets here and if you’ve got the kids, this family-friendly version is awesome.


The Chicago Pizza Tour is the perfect way to experience the Windy City’s diverse pizza scene! Their knowledgeable guides will take you on a delicious journey through some of Chicago’s most iconic neighborhoods, while sharing stories and history about this beloved food.

You’ll sample mouth-watering slices from several different pizzerias, each with its own unique style and flavor. You’ll also learn if locals really eat that much deep-dish pizza! 

So whether you’re a local looking to try some new places or a visitor wanting to explore the best of what Chicago has to offer, the Chicago Pizza Tour is an experience you won’t want to miss!


The Robie House is a Frank Lloyd Wright-designed building that is now on the campus of the University of Chicago. The building was designed as a single-family home, and was completed in 1910. It is considered to be one of Wright’s most important works, and is designated as a U.S. National Historic Landmark.

The Robie House is open for tours, and visitors can explore the building and learn about its history. The Frank Lloyd Wright Trust also offers educational programs and events at the Robie House.


Suppose you are interested in experiencing the history and culture of Chicago’s gangster past. In that case, a Chicago Gangster Tour of some of the most famous sites associated with notorious criminals, like Al Capone, John Dillinger, Bugsy Moran, and others, is definitely for you. There are numerous Chicago gangster tours that take you to many of the most famous sites associated with this city’s infamous criminal past.

Some of the most popular include visiting the sites of famous gangster crimes, like the Biograph Theater where John Dillinger was shot by FBI agents, or the site of St Valentine’s Day Massacre on Clark Street. You can also visit breweries that were once used as speakeasies during Prohibition, check out gangster hideouts and stomping grounds, or learn all about the history of gangsters in Chicago.


47 Best Things To Do in Chicago You Can’t Miss

Navy Pier is a great place to take your kids during the summertime. There are so many things for them to do, and it’s a great way to beat the heat.

At Navy Pier, you’ll find carnival rides and games, museums and attractions, boat cruises and tours, shopping, dining, and much more. Not only will your kids have a blast, but you will too.

When visiting Navy Pier, you must take a ride on the Centennial Wheel and enjoy breathtaking views of the Chicago skyline and Lake Michigan. Did you know Chicago is where the Ferris wheel was invented? Kids will also love taking a spin on the historic carousel found here.

Looking for online tickets to attractions or cool tours offering insider info? Get Your Guide is our family’s go-to resource for online purchases. Find Navy Pier Centennial Wheel Regular or Express tickets here.


If you are looking for a fun and affordable day out in the city, check out the Lincoln Park Zoo. Located in the heart of Chicago, this is one of the last free zoos in the country, making it a popular attraction for families and animal lovers alike.

At the Lincoln Park Zoo, you will find a wide variety of animals from all over the world, including lions, polar bears, and monkeys. There is also a children’s zoo area where kids can get up close to smaller animals, like goats and sheep.

Whether you are interested in seeing the magnificent animals or just want to spend a day outdoors with your family and friends, the Lincoln Park Zoo is sure to be a fun and memorable experience.


If you’re looking for a great place to take your kids to in Chicago, then you need to check out Maggie Daley Park. This beautiful park is the perfect spot for a family day of fun, with plenty of activities and attractions to keep your little ones entertained all day long.

Whether you want to go ice skating or play on the climbing wall, there’s something for everyone at Maggie Daley Park. And best of all, it’s completely free to enter!


If you’re looking for a fun family day out in Chicago, there’s no better place than the Chicago Children’s Museum. Nestled right on Navy Pier, this museum is packed with all kinds of fun activities that will keep your kids entertained for hours.

There’s something for everyone at this fantastic museum, from hands-on science exhibits to immersive artistic workshops. They have exhibits for all ages — from babies and toddlers to big kids.


Oz Park is one of the most charming parks in Chicago, and it has one special attraction that makes it even more special: a scavenger hunt for kids and families. This Oz Park statue “scavenger hunt” is the perfect way to explore the park and find all of the hidden treasures.

The scavenger hunt takes you on a tour of the park, starting at the north end near Diversey Parkway. You’ll wind your way through the park, following clues that will lead you to different statues. Each statue has a different Oz-themed character, and you’ll need to find all of them in order to complete the scavenger hunt.



The Adler Planetarium is a world-renowned leader in astronomy education and public outreach.

Each year, the museum welcomes more than half a million visitors from around the world, reaching millions more through youth STEAM programs, neighborhood skywatching events, online citizen science, and other outreach efforts.

It’s a great place to introduce kiddos to space and get them excited about learning!


The Midway Plaisance is a stunning public park in Chicago that offers visitors the opportunity to enjoy a variety of beautiful gardens, as well as interesting artwork. One of my favorite things about the Midway is its tranquil atmosphere, which makes it an ideal place for a relaxing stroll or quiet picnic with friends and family.

I would highly recommend a visit to the Midway Plaisance for anyone looking to escape the hustle and bustle of downtown Chicago.


The Peggy Notebaert Nature Museum is a great place to visit if you’re interested in nature and the environment. The museum has exhibits on a variety of topics, including plants, animals, and the history of the area. There are also interactive displays that allow you to learn more about the natural world.

The museum also offers a variety of educational programs and events, so there is something for everyone. Whether you’re looking for a fun day out with the family or educational activity for school kids, the Peggy Notebaert Nature Museum is definitely worth checking out.


Located in the North Park neighborhood of Chicago, Gompers Park is a lovely place to visit for families and outdoor enthusiasts. With its beautiful natural landscape and recreational facilities, Gompers Park offers something for everyone. Whether you are looking for a spot to play sports, enjoy the outdoors with your family, or simply relax by the river, Gompers Park is the perfect place to be.

One of the best things about Gompers Park is its convenient location. Situated at the corner of Foster and Pulaski Avenues, the park is easily accessible by public transportation or car. There is also ample parking available, so you won’t have to worry about finding a spot.

When you visit Gompers Park, be sure to take advantage of all the great activities it has to offer. The park is home to a fantastic outdoor swimming pool, complete with diving boards and a separate wading pool for younger children.

Suppose you prefer more active pursuits, head over to one of the many baseball fields or tennis courts. And if you’re looking to relax, take a stroll by the river or simply enjoy the views from one of the park’s many scenic walking paths.


47 Best Things To Do in Chicago You Can’t Miss



Located just south of downtown Chicago, the vibrant Pilsen neighborhood is home to some of the city’s most striking street art murals. Spanning from the Chicago River to Western Avenue, these dynamic works can be found adorning buildings and other structures throughout the neighborhood, painting its streets with color and vibrancy.

The 16th Street railroad embankment is particularly well-known for its street art, with dozens of murals from both local and international artists adorning its walls. Visitors can enjoy a self-guided tour of the murals, which range from intricate portraits to bold geometric patterns. The Art in Public Places Initiative, a local organization that supports street art in Pilsen, has also played a key role in bringing these beautiful murals to life.

Whether you’re an aspiring artist looking for inspiration or simply someone who appreciates the beauty of street art, a visit to Pilsen’s 16th Street Murals is sure to delight. So if you find yourself in Chicago, be sure to add this vibrant neighborhood to your itinerary (it also has an incredible food scene!).


Looking for something truly unique and spectacular? Art on theMart, the world’s largest permanent digital art exhibition, is just the thing. Located in the River North neighborhood, this stunning light show features incredible projections onto a 2.5-acre building known as theMART.

With both local and international artists showcasing their work, Art on theMart is a must-see for any art lover. And with over 30,000 visitors each year, it’s also one of the most popular attractions along Chicago’s Riverwalk.

Art on theMart is performed every evening, with showtimes varying depending on the season. So whether you’re in town for a quick weekend getaway or planning a longer stay in the Windy City, be sure to make time to see this spectacular light show and experience all that River North has to offer.


47 Best Things To Do in Chicago You Can’t Miss
Courtesy of Empty Bottle


The Second City is one of the most well-known comedy clubs in the country, and for good reason. Located in Chicago, this club has been the launchpad for some of the biggest names in comedy, including Steve Carell, Tina Fey, and Bill Murray.

There’s something exceptional about seeing a show at The Second City. The club has a long history of cultivating some of the best comedic talents in the world, and that tradition continues to this day.

The Second City is beloved by tourists and locals alike. If you’re looking for a laugh and decent drinks, there’s no better place to go than The Second City. 


Kayaking at night is a sensory experience like no other. The water is calm, and the city skyline is illuminated against the dark sky. It’s the perfect way to see Chicago from a different perspective.

Urban Kayaks offers night tours that are led by experienced guides who know the waters of Lake Michigan well. They’ll take you on a journey through the city, showing you all the best spots for getting a great view of Chicago’s skyline and architecture.

Whether you’re an experienced kayaker or a beginner, a night tour with Urban Kayaks is an experience you won’t want to miss. I try to take a tour at least once every summer!


The Green Mill is a beloved jazz club and local favorite in Chicago’s Uptown neighborhood. It was a popular haunt of the notorious mobster Al Capone.

Today, visitors will enjoy nightly jazz performances and cocktails. If you’re looking for a piece of true Chicago history with prohibition vibes, this is the spot!


The Empty Bottle is one of Chicago’s most beloved music venues, and for a good reason. Located in the heart of the city’s hipster-friendly Wicker Park neighborhood, the Bottle has been hosting killer shows since 1992.

The intimate setting (it only holds about 350 people) and top-notch sound system make it the perfect place to see up-and-coming bands or your favorite indie artists.


If you’re looking for the best blues club in Chicago, you’ve got to visit Kingston Mines. This historic venue has been a fixture of the local music scene since 1968, and it draws crowds of music lovers every night. Whether you’re a fan of traditional blues or more modern takes on the genre, you’ll find something to love at Kingston Mines.

The club has two stages, so there’s always something going on, and the lineup of performers is always impressive. So if you’re visiting Chicago, be sure to catch a show at Kingston Mines – you won’t be disappointed!


Rainbo Club (yes, that is how it is spelled), is one of the most popular clubs in the city. The Club is known for its great music, fantastic atmosphere, and friendly staff.

Rainbo Club is the perfect place to go if you want to have a good time and stand side by side with locals!


47 Best Things To Do in Chicago You Can’t Miss
Courtesy of Au Cheval


At 88 Marketplace, you can experience the vibrant food and drink culture of Chicago’s Chinatown in one convenient location. Featuring a wide selection of authentic Asian cuisine, from savory noodle dishes to sweet boba teas, this bustling food hall and grocery store is sure to delight any foodie looking to try something new and exciting.

Whether you’re in the mood for a steaming bowl of ramen, a mouthwatering banh mi sandwich, or some refreshing boba tea on a hot summer day, 88 Marketplace has something to satisfy your cravings. The food hall is packed with food stalls serving up everything from Japanese-style karaoke to Chinese dumplings, so you’re sure to find something to your taste.


Cindy’s Rooftop offers sweeping views of Lake Michigan and downtown Chicago. This rooftop is the perfect spot for grabbing your Instagram-perfect shots of the city. Plus, they offer creative and top-notch cocktails in the beautiful atrium space.

There is also a heated balcony, so you can enjoy incomparable views all year long. 


Locals say the wait is always worth it, when it comes to the famous burgers at Au Cheval. There are a few locations, but the iconic West Loop burger spot is the most well-known.

The menu is limited to essentially only burgers and fries (with a few other dishes here and there). So come hungry – these massive hunks of meat will leave you full and satisfied. 


If you’re looking for a unique dining experience in Chicago, then be sure to check out the many restaurants in Humboldt Park. Known for its Puerto Rican restaurants and culture, this neighborhood is home to some of the most authentic and delicious Puerto Rican restaurants in the city. Some popular options include Cafe Colao, ArePa George, and Nellie’s, all of which serve up classic Arepas and other tasty dishes.

Other notable restaurants in Humboldt Park include the recently reopened California Clipper, an upscale bar and lounge that serves up delicious cocktails. No matter what your taste, you’re sure to find something to love in Humboldt Park.


I recently visited the 2D Restaurant in Chicago, and it was a truly unique experience. The restaurant is known for its hand-brewed, made-to-order coffee, using the finest fair-trade coffee beans from Metropolis Coffee Company.

I ordered a cup of Phin coffee, which is brewed using a combination of pour-over and French press methods. The coffee was exceptional, with rich and complex flavors that were extremely enjoyable.

The real kick is that the cafe is covered in artwork that makes it appear to be 2D. You truly feel like you’re sitting in a comic book!


The LondonHouse is one of the most popular rooftop bars in the city. Its huge rooftop space offers panoramic views of downtown Chicago. This place is always hopping.

With different alcoves and spaces, you can find a section to hang out in that will match everyone’s vibe for the night. 


47 Best Things To Do in Chicago You Can’t Miss


Chicago is one of the largest cities in the United States. It has also been called by different nicknames over time, such as The Windy City and Chi-Town. There are many things that Chicago is known for, but here are some of the most popular.

  • The Skyline. Chicago has a very recognizable skyline, and is home to some of the tallest buildings in the United States.
  • The Food. Chicago is well-known for its deep-dish pizzas and delicious hot dogs.
  • Their Sports Teams. Chicago has two baseball teams — the Cubs and the White Sox!
  • The Museums. Chicago is home to many world-class museums, including the Art Institute of Chicago and the Field Museum.

Overall, there are many things that make Chicago such a special city. Whether you’re visiting or living here, there is always something new to discover in this vibrant city.


Chicago is one of the most exciting cities in the country, with a vibrant arts scene and tons of activities to keep visitors occupied. However, there are plenty of things to do for free. 

You can experience the city through its parks and green spaces. Chicago has just under 600 parks and several miles of lakefront, providing visitors with beautiful views and lots of outdoor space to explore.

You can also hit up one of the many free beaches around the city. Wherever you’re swimming or sunbathing, you will enjoy unbeatable views of the skyline.


One of the most popular family attractions in Chicago is the Shedd Aquarium. Home to over 32,000 aquatic animals, the aquarium is a must-visit. Kids will love learning about sea life and getting up close with the penguins and sea otters.

If you are looking for outdoor activities, Chicago has plenty of options. Visit one of the city’s beautiful parks, such as Millennium Park or Lincoln Park Zoo, for a day of fun in the sun. You can also head to the Lake Michigan shoreline and explore some of the city’s beaches.

And, if you want to sample some of Chicago’s famous food, there are plenty of kid-friendly restaurants in every neighborhood. Check out one of the local diners for a classic Chicago meal or try one of the city’s famous pizzerias for a slice of delicious deep-dish pizza.




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