A Complete Guide to the Best Things to Do in Chicago

Windy City Offers an Abundance of Opportunities for Just About Anyone

Whether you’re into art and culture, cuisine, or sport, the Windy City has something for you. Theatre lovers can choose between more than 200 stages and a plethora of plays and shows if they decide to move to Chicago. Blues and jazz are performed in numerous clubs, but let’s just mention Buddy Guy’s Legends. People here are also into outdoor festivals. Almost every weekend from spring to fall, the streets are crowded with tourists and locals alike.

The culinary scene in Illinois’ largest urban hub is rich and diverse. Whether you like street food or fine dining, from Italian to Indonesian cuisine, you can choose from more than 7,000 restaurants. You can book a table in Michelin-starred venues, or just classic burgers and pizza diners. With more breweries than elsewhere, Chi-Town is also considered America’s craft beer capital.

Do you enjoy bold architecture and breathtaking skylines? Take a boat cruise down the River or out on Lake Michigan to admire modern and historic buildings. If you are an adventurous type of person, take a look at the skyline from a glass-bottomed Ledge at Skydeck at the Willis Tower, or from the 94th floor of the 360 Observation Deck.

If this is too high for your taste, enjoy the lakefront with its numerous parks and beaches connected by the scenic Lakefront Trail, where you can walk, run, bike, or engage in all kinds of summer activities.

Sports fans will definitely want to visit the Cubs stadium in the north part of the town, the second-oldest baseball field in the country. Or see the famous White Sox play at Guaranteed Rate Field. If basketball is your game, or maybe hockey – head to the United Center to see the Bulls and the Blackhawks.

With so many things to offer, you will want to get in touch with a Chicago moving company and see everything it has to offer as soon as possible.

Visit the Art Institute of Chicago

Being one of the oldest museums in the country with huge capacities, this facility has been ranked among the best ones of its kind for years. It was founded in 1879, and it houses one of the largest Impressionist and Post-Impressionist collections in the world. Located near The Loop, it showcases more than 300,000 artistic pieces, from Etruscan pottery and Ancient Greek reliefs to the works of Picasso, Georges Seurat, Vincent van Gogh, Grant Wood, and many others. Visiting this place will feel like a journey through different cultures and centuries, and you will have a chance to take a glimpse of the Byzantine, medieval, Renaissance, and modern works, from China to Africa.

You will be able to see paintings and masterpieces of the most famous painters in the world. There are sculptures dating from the 12th to the 20th century, bronzes, ceramics and jades from Asia, covering China, Korea, Japan, India, the Middle East, and the Americas. The artists whose works are displayed in the Art Institute include Sargent, Stieglitz, Whistler, Rivera, and a whole range of modern and contemporary pieces, including Warhol, Pollock, and other famous authors.

Spend Your Day Enjoying Contemporary Art

If contemporary art is your cup of tea, then head straight to Chicago’s Museum of Contemporary Art, overlooking The Loop and Lake Michigan from its sculpture garden. You will be able to admire the most exciting exhibitions since 1945, take a break at the restaurant, and buy some souvenirs in the gift shop. It was here that Frida Kahlo had her first US exhibition, and Jeff Koons had his first solo display.

Gaze at Frank Lloyd Wright’s Architecture

For fans of Frank Lloyd Wright, Chi-Town will be a bliss. Oak Park is one of the best neighborhoods in Chicago for architecture lovers. It is home to the most extensive collection of Frank Lloyd Wright’s structures in the world. From private residences to facilities open for public and UNESCO World Heritage Sites, you can observe a Frank Lloyd Wright history in Chi-Town. Starting with the Wright Home & Studio, where he designed and built almost a quarter of his life’s work.

Go to the Chicago History Museum

This facility was initially founded in 1856, but the building, along with its collection, burned down during the Great Fire of 1871. The collection was subsequently renovated, and today it has collections embodying Chi-Town’s past and present, as well as the future. It has a mission to connect people by sharing stories through which we all learn and identify ourselves.

See a Mummy at the Field Museum

One of the greatest museums of natural history, comprising more than 24 million objects, displays items from ancient cultures to contemporary time. It opened for public in 1894 near The Loop, exhibiting a collection of artifacts from the 1983 World Fair. Today it explores billions of years of natural history, allowing you to take a look at an ancient Egyptian tomb and discover other ancient civilizations, starting from the prehistoric era.

Visit the Chicago Cultural Center

This venue takes up an entire block and organizes more than 700 free programs a year. It allows you to see exhibitions, film screenings, lectures, and performances every day under the same roof. That’s why it is considered one of the most comprehensive US arts showcases. Even a short tour will open your eyes to the world of splendor, starting from the 30,000-piece Tiffany-stained glass dome, the largest of its kind in the world, to the mother of pearl mosaics and a Carrara marble lobby.

You Can Enjoy Art for Free at the Center

The good thing about this place is that there’s a variety of activities you can enjoy free of charge, such as rotating exhibits, music concerts, film screenings, theatre and dance, lectures, and workshops, including the ones for children. There are also free tours of this architectural gem. One of the curiosities is exploring an extensive underground pedestrian walkway system called the Pedway. It connects more than 50 buildings across 40 blocks, starting from the Randolph Street Lobby of the Cultural Center.

Best Things to Do in Chicago for Free

Speaking of free things, there are museum days when Illinois residents have a chance to get admitted without any charge. You can also get the CityPass or some other card that enables discounts for certain attractions. Just ship your car to your new home and start enjoying different attractions and monuments.

Chicago’s Architecture Center even offers educational programs all year round that are free of charge. You can also see a 3D model of the town in its headquarters near The Loop. There is also a Greeter Program that arranges guided tours to match your interests. The Lakefront Trail offers various outdoor activities you can enjoy without any charge, as well.

One of the Popular Things to Do in Chicago Is to Visit the Bean

The Bean, which is a popular name for the Cloud Gate, is a monumental permanent outdoor installation unveiled in 2004, surrounded by green space and serving as the entrance to Millenium Park. When designing this reflective sculpture, the artist Anish Kapoor, an Indian-born British sculptor, was inspired by liquid mercury. The surface reflects the lights of Michigan Avenue, the surrounding skyline, and people passing by, creating a unique experience.

The Riverwalk Is the Best Place to Take a Walk

The Riverwalk was once a smelly shipping channel, which has evolved into a picturesque downtown attraction. Apart from a romantic walk along the river, this area offers a range of entertainment options, from kayaking and boating to bike riding, eating and drinking, or just enjoying this enchanting blend of nature and urban life. So enjoy your day by the river while you adjust to your new town.

See 200 Species of Animals at the Lincoln Park Zoo

Lincoln Zoo is one of the oldest animal parks in North America and one of the most beautiful free-admission zoos. It integrates modern exhibits with the traditional architecture of the past. Apart from having an opportunity to watch around 200 species of wild animals in their natural habitats from up close, Lincoln Zoo also has one of the largest conservation and science programs in the country. The Lincoln Zoo has been updated regularly and offers the most contemporary education on this topic. Among other attractions, you can opt for the Sea Explorer 5D, a virtual submarine adventure, a close encounter with penguins in the Pritzker Penguin Cove, or AT&T Endangered Species Carousel.

Walk Through the Gardens in the Garfield Conservatory

This conservatory spans across a 12-acre garden space, both indoors and outdoors. It is one of the largest under-glass gardens in the world, home to the national botanical treasure consisted of thousands of plant species from all over the world, available to visitors free of charge. There are also a water lily pond, play spaces for children, and more.

Listen to Music at the Jay Pritzker Pavilion

The Jay Pritzker Pavilion is an open-air venue located centrally in Millennium Park and designed by a famous award-winning architect Frank Gehry in his signature Deconstructivist style. This sculptural construction composed of a network of stainless-steel ribbons framing the stage is one of the premier outdoor amphitheaters in the town. Besides performances by the Symphony Orchestra, it features jazz, blues, and other world music events and a variety of cultural performances.

Enjoy the Collection of the Smart Museum of Art

The Smart Museum of Art at the University of Chicago was founded in 1974 by brothers David and Alfred Smart, who also launched Esquire Magazine and built a publishing business in Chi-Town. Its permanent collection has over 15,000 objects, and it organizes innovative exhibitions and programs, combining diverse ideas and experiences to create unique and bold initiatives and tackle complex issues through artistic practice. It is open to the public without any charge. It receives support from the family foundation and various partners, including the University.

Try the Baseball Field at the Humboldt Park

Humboldt Park is located in the heart of the Humboldt Community, now a predominantly Puerto Rican neighborhood that covers an area of about 197 acres. Apart from a fieldhouse with a fitness center, gymnasiums, meeting rooms, inland beach, and lagoons, it features baseball and soccer fields, tennis courts, and a replica of the Cubs stadium known as “Little Cubs Stadium.” But, along with sports and recreation, it offers cultural entertainment, such as Latin Jazz Festival and the Puerto Rican Festival. And since it provides an urban-suburban mix feel, it is also one of the best places to live in Chicago.

Catch a Game at Wrigley Field

Wrigley is the second-oldest baseball park in the country and home to the 2016 World Champions – the Cubs. Located in the north part of the city, it has evolved significantly throughout its history, which spans more than 100 years. In 2014, a new restoration process called the 1060 Project started, which is supposed to improve its functionality by additional upgrades of its structure and amenities while still preserving its historic features and charm.

Cheer for the Bulls and Blackhawks at the United Center

A product of a partnership between the owners of the Blackhawks, the renowned hockey team, and the Bulls, the world-famous basketball team, United Center is the largest sports arena in the States. Since its opening in 1994, it has received over 40 million guests and hosted over 200 events every year.

Other than the extremely popular basketball tournaments and ice championships, some extraordinary artists played here, including Eric Clapton, The Rolling Stones, Bruce Springsteen, The Who, U2, and many more. There are tours for fans on non-event days that allow them to experience a part of the glorious history and walk the halls of some of the sports’ legends such as Michael Jordan.

Explore an Elevated Trail on the 606

Situated on a former industrial railroad line, this is a recently built system of green trails and parks which covers four different neighborhoods: Wicker Park, Bucktown, Logan Square, and Humboldt Park. It is accessible every quarter mile through 12 access points and 17 access ramps for disabled people.

Its official name is the Bloomingdale Trail, but it was given a casual name 606 after the common zip codes on the west side. The trail will allow you to enjoy views from some look-out points, visit the outdoor observatory, see public art installations, participate in community bonfires and astronomy nights, walk, bike, and jog.

See the City From Above at the Willis Tower Skydeck

This 110-story town icon is the eighth tallest building in the world and the tallest one in the Western Hemisphere. Therefore, it is no wonder it’s a perfect observation spot, offering stunning views. The Skydeck enables you to see four states, while the removed perimeter structural steel at the sides makes the edges almost invisible. Its extended glass balcony on the 103rd floor, called the Ledge, provides visitors with an exciting experience of looking down through the glass floor. Besides the view, visitors can take part in interactive and educational attractions which celebrate the town’s architecture, culture, sports, history, food, and people.

Grab a Ride at the Centennial Wheel

Another local icon is the Centennial Wheel at the Navy Pier. This almost 200-feet-high wheel offers a 360-degree view of Chi-Town and Lake Michigan. It was built to celebrate the 100th anniversary of Navy Pier, hence the name. It has 42 gondolas, electrical doors, and a high-resolution video screen. The Wheel is open all year round depending on the weather, as severe weather conditions such as lightning, high winds, and extreme cold can make it unsafe.

Spend a Day at the Shedd Aquarium

The Shedd Aquarium hosts 32,500 water creatures from all over the world. A unique experience is getting face to face with beluga whales, dolphins, sea lions, and penguins in the Abbott Oceanarium. There are aquatic presentations with dolphins and belugas and a special exhibit called Underwater Beauty. If you’re a fan of sharks, you can see them in Wild Reef. Children can enjoy the permanent exhibition called Polar Play Zone.

Try Tasty Food at Some of the Best Restaurants the City Can Offer

Chi-Town’s culinary scene is diverse, offering an array of cuisines, from fine dining to street food, from Italian to Indonesian. There are more than 7,000 restaurants in Chicago, including Michelin star winners, so making friends in a new city over some delicious food won’t be a problem. The famous dining districts are Restaurant Row and Fulton Market, but you can experience an array of international cuisines in the neighborhoods such as Chinatown, Little Italy, Greektown, Pilsen, etc.

Worth visiting is the summer food festival, the largest of the kind in the world, organized in July. The most popular dishes are deep-dish pizza, special hot dogs, Italian beef, and others. Along with the skill of culinary chefs, the food scene here is known for its fresh ingredients from Illinois farms. Inspired by street meals and rich in flavors ranging from Indian and Thai to Mediterranean and Mexican influences, Proxi is one of the places you shouldn’t miss, especially if you enjoy drinking exciting cocktails.

If you are a pasta lover, head to Monteverde, which offers affordable, seasonal dishes in an unusual setting with a centrally positioned bar. Inspired by Danish cuisine, Elske offers dishes marked by a personal touch in a cozy environment with an outdoor fireplace. Just as the name suggests, Mr.Beef is attracting visitors, among them local celebrities, with an excellent street-style Italian beef sandwich. In contrast, Osteria Langhe offers a stylish Italian experience of Piedmontese cuisine, focusing on a variety of wines.

See What Time Out Market Has to Offer

Situated in the heart of Fulton Market, Time Out has gathered culinary experts of various backgrounds in its 18 highest-rated local restaurants, 4 bars, and one rooftop terrace. Depending on what you like, you can get great pizza at The Art of Pizza or visit Arami’s sushi for something different. Abe Conlon has a lot of rustic dishes inspired by Portuguese cuisine, while Brian Fisher has an array of Asian-inspired recipes, featuring whole roasted duck that runs out real fast. If you want to try some Mexican cuisine, go to the Dos Urban Cantina. For flavoury dishes combined with excellent beers, go to Band of Bohemia, the first pub in the world to earn a Michelin star. Whichever option you choose, you cannot go wrong with food in this town.

Visit Some of the Finest Craft Breweries

If you want to feel the true spirit of the community, you have to visit some of its craft breweries. There are famous ones such as Revolution, Goose Island, or Half Acre, as well as smaller ones such as Hopewell, Begyle, Off Color, and others. You can also take a tour called the Chicago Beer Experience or attend some of the annual beer festivals, such as Illinois Craft Beer Week in May, to name just one.

The expansion of breweries over the past ten years has raised their number to over 200. Without trying to underestimate any of them, we can mention the Half Acre Beer Company. Founded in 2006 and regarded by experts as one of the finest, the beer that launched them was Daisy Cutter with hints of blended papaya, mango, pine, and citrus. Then there is Metropolitan Brewing, which has served German-style beers and lagers since 2009. It favors simple, easily drinkable beers, such as Krankshaft, with lemony flavor.

Revolution Brewing has revolutionized the scene with its aggressive-flavor beers such as Anti-hero and First City. Goose Island Beer Company practically started the beer-drinking era, which then expanded with other breweries. They serve high-quality beers, starting from a locally known 312, to certain food-focused beers and ending with Bourbon County Stout, with flavors ranging from chocolate to vanilla, caramel, and smoke.

Go to Concerts in the Millennium Park

Outdoor fun is always appreciated, especially if accompanied by music. Millennium Park offers this combo during its annual Music Festival – an outdoor classical music festival that lasts for ten weeks and can be visited free of charge. You just have to choose your picnic spot and indulge in the music performed by the Grammy-nominated Orchestra and Chorus delivered to you through the Pritzker Pavilion’s top sound system.

If you prefer gospel, there is an annual gospel music festival, as well, blending traditional and contemporary music, also without any charge.

House Music Festival takes place in May and features DJs and live performances. In fact, it is from this town that the new music form, house music, had expanded internationally.

The Blues Festival is the largest free blues festival in the world, earning the town its nickname “Blues Capital of the World.” It lasts for over three days and takes up five stages, where both renowned and local talents perform.

Jazz Festival, taking place from the end of August to the beginning of September, is among the oldest and most popular festivals, famous for its creativity in all forms of jazz.

Catch a Play at the Steppenwolf Theatre Company

When Gary Sinise, Jeff Perry, and Terry Kinney, at the time unknown actors and high school friends, formed this theatre, they probably didn’t think it would become the premier ensemble theatre in the country. However, its top actors, directors, and playwrights and their provocative productions won numerous awards, among which 12 Tony Awards, earning this theatre a legendary status. It not only produces world-class plays but also promotes the education and development of young authors. Even though mostly locally based, some performances even had international success, like August: Osage County, to mention just one.

Grab Your Popcorn and See a Movie at the Music Box Theatre

The Music Box Theatre has been operating since 1929. It was built at the time when sound films were a novelty, so the design included an orchestra pit and organ chambers, just in case the sound films failed. It has 700 seats and is owned by Southport Music Box Corporation – SMBC. It has been screening classic films, but also independent and foreign films. From older traditions of showing White Christmas to the new initiatives of horror movie film festivals and a yearly screening of A Space Odyssey, as well as Rocky Horror Picture Show, there is something for everyone. Just grab your popcorn and take a seat.

See a Comedy Show at the Second City

This initially small cabaret theater evolved into a premier sketch comedy theatre. It has not only been performing but also educating ensemble members for more than 50 years, creating a group of successful alumni comprising Dan Aykroyd, John Belushi, Chris Farley, Bill Murray, and many more. This place has spread world-wide, creating training centers, theatrical ensembles, and touring companies, but also establishing relationships with television and film productions to promote collaboration among all industry sectors. One of their most famous sketch comedies is: “Do you believe in magic?”

Feel the Beat of Its Non-Stop Nightlife

You cannot get bored in this town, that’s certain. Which form of entertainment will you choose depends only on your current mood. This town has it all, whether you are in for a craft cocktail or a drink with a view from some rooftop bar, or you just feel like dancing the whole night. The most famous bars include Three Dots and a Dash, Celest, The Violet, and many more. Maybe you would love to see the birthplace of house music? Head to Spybar! For drinks with a view, visit NoMi Lounge, Cerise rooftop at Virgin Hotel, or any other out of many rooftop bars available.

Music is deeply rooted here, so the variety of music genres to choose from is enormous. One of the neighborhoods with the most dynamic music scenes is Uptown, with Riviera Theatre and Wicker Park.

Listen to Late-Night Jazz at the Green Mill

Featuring all jazz styles, from traditional to bebop, contemporary, and improvisational, the Green Mill got its name from the famous Moulin Rouge in Paris. It had various owners from its foundation in 1907, including Al Capone’s gang member “Machine Gun “Jack McGurn. Al Capone used to visit frequently and even had his favorite booth (which is still there) from where he could see both entrances. There is even an escape route Al Capone used to elude the authorities through the tunnels under the street. Since then, the Green Mill regained its reputation as a popular jazz venue where some of the most famous musicians performed, including Billie Holiday and Al Jolson, and cabaret icons like Texas Guinan.

Discover New Bands at the Empty Bottle

This bar and music venue hosts mostly local, regional, and alternative music events, but also rock’n’roll, metal, indie-rock, punk, hip-hop, jazz, electronic, and experimental music. It is open every day and has performances every night. The place started as a simple bar serving beers and offering pool games and music from a jukebox. It has kept reasonable prices, creating a bunch of regular visitors contributing to its success.

Find Your Favorite Album at the Local Record Stores

One of the perks of the town is that it has preserved even its record store scene, cherishing both old stores that haven’t changed in decades and new ones in all their shine. Out of a variety of stores, we will mention Dusty Grove, ranked as one of the best in America by Rolling Stone. On the other hand, Reckless Records features mostly local and indie bands while Laurie’s Planet of Sound is famous for its “Do Not Buy Ever” list, referring mostly to Pitchfork music.

Spend Your Winter at the Millennium Ice Rink

What is there better to do outdoors in the winter than skate? Well, Chi-Town has you covered in that department, too. Among a number of ice rinks offering lots of fun, the McCormick Tribune Ice Rink is among the most popular ones.

Sunbathe at the Oak Street Beach During the Summer

The vast array of beaches in this town offers plenty of fun during the summer. One of the most popular beaches is Oak Street Beach on the shore of Lake Michigan, where apart from sunbathing, you can play volleyball, rent a bike, or other water sports items. If you are skilled, you can participate in some of the amateur or professional volleyball tournaments organized throughout the summer.

Relocate to the Windy City and Enjoy What It Has to Offer

Don’t let the nickname dissuade you from relocating to the third most populated city in the US, as you will quickly get used to all the good things that Chi-Town has to offer. Whether you choose a family-friendly Edgewater or traditional Irish-American Bridgeport, Mexican-influenced Pilsen, African-American Bronzeville, or any other ethnic community, you will feel at home as soon as you settle in. So check the cost of living in Chicago, book your moving services, and don’t miss out on what the city has to offer.