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Things To Do in Chicago, Illinois

24 local experts
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Is Chicago boring? Is it fun? How do people relax in their free time? From playing and watching live sports to listening to live music to volunteering, here's what 24 local experts had to say about things to do in Chicago, Illinois.

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Mobs on the streets beating anyone they see, smashing windows on cars, stealing. The police are not allowed to do what’s necessary because the mayor won’t let them. Criminals run the city. Not safe to live here or visit. Tourist are the favorite target for criminals, gangs, flash mobs. Very high taxes.

If you are planning to move to Chicago, plan to dress warm in the fall and winter. Get comfortable with using public transportation, because driving in this city is a nightmare and parking is close to impossible. However, the museums, restaurants and music scene more than make up for the challenges in Chicago.

Avalon, says: 2020

Chicago is a diverse city with plenty of good places to explore. Every neighborhood has its own distinct personality and charm. Those who enjoy cuisines from around the globe can visit Pilsen, Chinatown, Little Italy, Little India and Lincoln Square to experience a little bit of everything. Visitors will also love taking a walking tour around the Riverwalk to take in all the architectural sites that line the city’s skyline.

Kalecia, says: 2020

Chicago is a bustling hub of famous music, architecture, sports, museums, and mouth-watering food! My beloved Windy City is comprised of magnificent skyscrapers (Willis or Sears Tower, depending on who you ask), a beautiful lake with a neighboring trail, and a transit system that can connect you to all kinds of parts all over the city.

Melissa, says: 2020

Chicago is a great city! Summers in Chicago are beautiful and there are many activities. We have great parks and the beautiful Lake Michigan. Chicagoans love to play softball in summer, go to Cubs games, and spend summer evenings having bonfires and grilling with friends!

Chelsea, says: 2020

If anyone were moving to Chicago, my first recommendation would be to do your research! Chicago is an amazing city but without mapping out a game plan prior to moving, it can come off as overwhelming. For example, it is highly recommended that you research the different neighborhoods in Chicago to find which would be the best area for you to live in based on your needs. If you are searching for a neighborhood that is very convenient to local shopping, for example, something closer to downtown may be a better for you. If you seek a more quiet, residential area, something closer to the North side of the city may be more appropriate. Research helps with that! I would consider figuring out your top five most important criteria for a neighborhood and then locate an area based on that; chances are, Chicago has an area that can suit you!

Katherine, says: 2020

Chicago is a diverse metropolis. There are areas of great wealth, and areas of extreme poverty. There are people of every race, religion, and ethnicity. There are a wide variety of activities in which to participate, for families, couples, or individuals. No matter what your interests are, you can find something to do in Chicago.

Rachel, says: 2020

Those moving to Chicago should first familiarize themselves with Chicago’s diverse neighborhoods. I prefer the Near North Side because it’s safe and less chaotic than the Loop, but still offers an abundance of terrific dining and shopping venues. However, if you’re looking for a more traditional housing arrangement within the city limit then take a look at the North and Southwest suburbs.

Dolores, says: 2020

Chicago is a beautiful, urban city in Illinois. With some of the highest rated restaurants in the country, beautiful parks, and the riverwalk, it also one of the most densely populated cities in the country. If one moves to Chicago, they must be prepared for an elevated cost of living, including the price of rent.

When many people think of Chicago, they think of a cold, windy city. In reality, Chicago is a great outdoor city where its residents can enjoy many warm-weather activities, such as biking, kayaking, or running. With a location along Lake Michigan, Chicago is also home to many water sports, like surfing and boating.

Heather, says: 2020

If Chicago is one’s city of preference for relocating, there are a few highlights to consider. Some of these highlights include harsh winters, great food, and an abundance of cultural activities. Chicago is a lively city with plenty of things to do on the weekend for those who enjoy a pleasant nightlife.

Chicago is at its most seductive in summer. There’s loads to do, from patio dining to lakeside lounging. The whole city comes alive when the sun comes out. Wintertime, however, is another story. To survive almost eight months of extreme cold, chilling precipitation, and malevolent winds, one must have a thick winter coat and even thicker skin.

Katelyn, says: 2020

Chicago is a city of many neighborhoods. It’s right next to Lake Michigan and has the longest stretch of park in the northern hemisphere. It is home to many sports teams. It has many outstanding universities. There are many art and music festivals throughout the year. It is Carl Sandburg’s “city of broad shoulders”. It has wonderful museums and restaurants featuring all types of cuisines.

Lauren, says: 2020

Chicago is the home of the Blackhawks and the Cubs. Chicago is the third most populous city in the U.S. There is always something to do — The Taste of Chicago where there are tons of vendors serving foods from different cultures, New Year’s Eve at Navy Pier where you can see beautiful fireworks, live comedy shows and musical artists at the House of Blues. You can go to the zoo and conservatory, get lost in downtown or just hang by Buckingham fountain in Millennium Park.

Jermaine, says: 2020

Chicago is a very historical and large city with many things to offer. It was the home of the World’s Fair and at one point the hub for Al Capone and his mob. The Windy City as it is often referred to due to its history of political corruption, does however house rich cultural diversity, top notch restaurants, known for deep dish pizza and the Chicago style hot dog. The city is home to some of the country’s largest museums like the Field Museum and Museum of Science and Industry. It is constantly developing and one always can discover something new. Finally, it is a wonderful city to raise a family.

Ressie, says: 2020

Chicago is famous for Chicago-style hot dogs, Chicago-style (deep dish) pizza, Maxwell Street Polish Sausage, jazz music, and 1920s gangsters like Al Capone. Chicago is also known for interesting architecture like the Sears Tower, many museums, and many loyal sports fans. While it is widely known as the “Second City”, Chicago dropped to third in the US by population in the 1990 Census. On the shores of Lake Michigan, Chicago is the largest city in the Midwest.

Trinity, says: 2020

There’s always something to do no matter the season. There are many events, festivals, and concerts to go to in Chicago. You won’t be bored, especially with dozens of food choices from soul, Indian, Mexican, Chinese, Thai and so much more.

Chicago has reliable transit and bike lanes, forests to trail in and botanical gardens to observe. There are alleyways instead of trash on the street. Diverse and well-integrated, the people carry a Southern niceness and pride. They enjoy engaging in pleasantries and do not tolerate false niceties or phony behavior. The city is rich in its knowledge and varying institutes, home to the first ever planetarium and highly esteemed galleries of art (the Art Institute of Chicago being the top-rated museum in the world).

Chicago, known as the windy city, is known for its lively and rich cultural heritage. From fun walks to educative and explorative museums, you can keep yourself busy and have fun in Chicago. Surrounded by a sprawling music scene and theater and dance, you will be culturally satisfied in the city.

The streets of Chicago are bustling. There is a certain rhythmic heartbeat to the hours spent riding the subway downtown. The atmosphere is ever changing, with the city’s various glitzy high rises to the post-industrial scenes. Each and every Chicago neighborhood has its own distinct culture, history, and experience to soak in. Authentic ramen and mochi available to purchase from Asian marketplaces, traditional meat dishes sold in Greektown.

Albany Park, located just 20 mins from downtown Chicago, is home of the bean, the Willis tower and also known as the best place to live. Chicago is a bustling urban center home to many. Chicago is clean. Downtown Chicago has an annual Christmas tree and ice skating rink at Millennium Park with the perfect view of the Bean. It has businesses like a whole Nutella cafe and a speciality donut shop. There’s much to do here if you want to hang out at Maggie Daley park, visit the several museums located there, or go visit the gigantic tourist attraction known as the Bean.

Nokware, says: 2020

Chicago is a beautiful town with world-class restaurants, top shopping, a great lake with beaches, and warm people. Just beware that winters can quite brutal, with temperatures dropping below zero quite frequently, especially in the early months of the year. But the sights of snow and a white Christmas make up for the chilly weather.

Chicago is a very diverse city. We have beautiful downtown and lakefront that offer many attractions. The people are friendly and love to help. While downtown is bustling, the neighborhoods that lie at the edge of the city have a suburban feel to them. The food is out of this world. From upscale fine dining to neighborhood pizza places. There’s something for everyone in Chicago.

Taylor, says: 2020

The City of Chicago is the largest city in Illinois and the third-most-populous city in the nation. Chicago has a multitude of museums, including the prestigious Art Institute and the Chicago Historical Society. Families will find plenty to do at Navy Pier and to explore at the Field Museum and the Lincoln Park Zoo. You could spend all day strolling through Hyde Park or shopping along the Magnificent Mile.

Taylor, says: 2020
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