The Windy City is chock-full of job opportunities, diversity, and family-friendly activities, drawing relocating young adults, families, and retirees. Here are 16 pros and cons of living in Chicago!

Pros of Living in Chicago

A post shared by @instagram

Moving to Chicago means having access to lots of big city amenities. Here are 12 pros to Chicago living.

Pro: All the Career Opportunities

With over 2.5 million residents, Chicago is the third-biggest city in the U.S., with numerous businesses and career opportunities in the city center and beyond. The top industries include healthcare, science and technology, education, and retail, but you can find a career in every industry in the Chicago area. It also hosts the second-largest amount of Fortune 500 company headquarters in America, including Exelon, AbbVie, Hyatt Hotels, and CME Group. Some of the best places to work in Chicago are Berkshire Hathaway HomeServices Chicago, Charles Schwab, and the Ace Hardware headquarters in Oak Brook. Additionally, Chicago is known for being a great city for entrepreneurs with all kinds of startups and small businesses, so it’s the perfect place to start your own business!

Pro: Tons of Higher Education Options

You can get a top-notch education from several Chicago colleges. Create lasting memories at the largest university in Chicago, with majors including business and biology at the research-based University of Illinois Chicago. Study social sciences, mathematics, and more at The University of Chicago, one of the best universities in the United States. Study game design, animation, or entrepreneurship at Catholic DePaul University. Enroll in classes for engineering, computer science, or architecture at the innovative Illinois Institute of Technology (Illinois Tech). Earn a degree in marketing, biomedical science, psychology and more from the private Loyola University – Chicago. Or jump in to programs like accounting and musical theatre at a school that’s a national leader in developing socially conscious students at Roosevelt University.

Pro: Chicago Transportation Is Easy

With all the various transportation options, traveling in and out of Chi-town is a breeze. Due to its centralized location and diverse population, Chicago is a major travel hub with two huge airports: O’Hare International Airport and Chicago Midway International Airport. Travel to the Chicago suburbs and a few nearby cities on 11 lines with the Metra Rail, a train system that ensures accessibility for all. Get around the city of Chicago with one monthly pass by train (aka “the L” train) or bus with the second-largest public transportation system in the country, the Chicago Transit Authority (CTA). Combine sightseeing with a legitimate transportation option on the Chicago River with Chicago Water Taxis or Shoreline Water Taxis. Ride to your destination in bikeable Chicago on your own bike, or rent a scooter, classic bicycle, or ebike from Divvy Bikes.

Pro: A Diverse, Friendly City

Proof of Chicago’s diversity is everywhere within its 178 neighborhoods! In fact, Chicago is the most immigrant-friendly city in the U.S. for many reasons, including access to government aid like food stamps and welfare, as well as resources for immigrants and refugees, like Centro Romero and the National Immigrant Justice Center—which assist with transitions to American life. Additionally, this populous city has representation in several religions, orientations, backgrounds, and walks of life, and that’s reflected in the attitudes of Chicagoans. Generally, the people are welcoming, inclusive, and proud of their diversified metropolis.

Pro: Chicago Has Pride

Speaking of inclusivity—Chicago is one of the top ten most LGBTQ+ friendly cities in the country. In 1997, Northalsted, also called Boystown Chicago, became the first official gay neighborhood in the nation! If you need community resources while in the Chicago area, the Brave Space Alliance, Center on Halsted, Equality Illinois, and more are happy to help. There are a slew of fun Chicago LGBTQ+ things to do, and the city celebrates Pride all year long! Party with the community with live music on five stages, over 250 vendors, and dance exhibitions at Northalsted Market Days, one of Thrillist’s Can’t-Miss Queer Events. March in or watch the Chicago Gay Pride Parade, complete with floats, bands, and colorful vehicles, and attend some of the other events of Chicago Pride Month like Chicago Pride Fest. Looking for a drag show in Chicago? Catch diva-filled weekend brunches and nightly tableside shows at the Kit Kat Lounge. Or relax with a drink and excellent music at Chicago gay bars like Big Chicks and lesbian favorite, Nobody’s Darling.

Pro: Kid-Friendly Things to Do

If you’re looking for family-friendly activities in Chicago, you won’t be disappointed! Snap a photo with Cloud Gate (aka The Bean) and other public art, splash around in Crown Fountain, and walk through the beautiful Lurie Garden in Millennium Park. Take the BP Pedestrian Bridge to climb the rock wall, play mini golf, and ice skate in the winter at Maggie Daley Park. Swim, cook hamburgers on a grill, and catch some rays on Lake Michigan at North Avenue Beach. Explore exhibits like the Waterfowl Lagoon and Helen Brach Primate House, see and learn about African lions, American beavers, and chimpanzees, and stroll the Conservation & Science Gardens at the free Lincoln Park Zoo. Go behind the scenes with penguins, sharks, and beluga whales, participate in cool events like Teen Nature Days, and watch stingrays, green sea turtles, and sea otters swim at Shedd Aquarium. Grab a seat on rides like the Centennial Wheel and Tea Cups, catch fireworks shows, and attend themed events like March Into Spring along the Lake Michigan shoreline at Navy Pier. Or shop for dolls and accessories and go to the salon with your doll and have a real tea party at the American Girl Doll Store.

Pro: Find Skill & Mastery in the Chicago Arts Scene

Get a little culture with the countless opportunities for arts and entertainment in Chicago. Attend concerts from big names like Ash, The Wallflowers, and Laufey at Chicago music venues like Thalia Hall and The Chicago Theatre. Listen to both classical and modern music including Bach and Herbie Hancock by the Chicago Symphony Orchestra. See performances of Aida and Rising Stars in Concert with the Lyric Opera of Chicago. See shows like My Fair Lady, Peter Pan, and Mamma Mia! from Broadway in Chicago at venues like the James M. Nederlander Theatre and Cadillac Palace Theatre. Celebrate the art of dance with stunning shows by The Joffrey Ballet and Deeply Rooted Dance Theater. Admire both performance and physical art at some of the best Chicago art galleries, including the Hyde Park Art Center, Corbett Vs Dempsey, and the Rhona Hoffman Gallery. Find exceptional Chicago public art like the digitally-projected Art on The Mart, The Picasso by Pablo Picasso, and bronze Statue of the Republic. Or laugh along at famous comedy locales including Zanies Comedy Night Club and The Second City—the precursor to Saturday Night Live in New York.

Pro: Exciting Museums

There are so many interesting museums in Paris of the Prairie that you might not get to all of them with just one trip! Visit fascinating exhibits like Science Storms, sit in the Giant Dome Theater for exploratory films like Dark Universe, and control aircraft in the Flight and Motion Simulators at the Museum of Science and Industry. Learn something new with displays like Astronomy in Culture and shows like Imagine the Moon at the Adler Planetarium, the first planetarium in the U.S. See real mummies in the Inside Ancient Egypt exhibit, sit inside a Pawnee Earth Lodge, and meet Maximo the Titanosaur—the largest dinosaur ever found—at the Field Museum. Fall back in time with urban history seminars and exhibits like Facing Freedom in America and City on Fire: Chicago 1871 at the Chicago History Museum. Spend the day viewing the Impressionism and Fashion collections, exhibitions like Radical Clay: Contemporary Women Artists From Japan, and the famous lion sculptures in front of The Art Institute of Chicago, one of the biggest museums in the world. Experience exhibits like Mariachi Potosino, performance art pieces like Wilma, or kid-friendly events like Listo para el museo: Storytime in the Galleries at the National Museum of Mexican Art. Or immerse yourself in creativity with permanent exhibits like A Nation of Writers, temporary exhibits like Level Up: Writers & Gamers, and events like Get Lit: Poetry in Bloom at the American Writers Museum.

Pro: A Sports Lover’s Paradise

No matter your sport, moving to Chicago means you have plenty of teams to cheer for all year long. Watch the Chicago Bears (NFL) score touchdowns at Soldier Field. Root, root, root for the Chicago Cubs (MLB) at the iconic Wrigley Field. Cheer on the Chicago White Sox (MLB) while they take on their rivals at Guaranteed Rate Field. Bring a friend to support the Bulls (NBA) at United Center—or get tickets to see fantastic backhand shots at a Chicago Blackhawks (NHL) hockey game. Or enjoy watching the Chicago Sky (WNBA) at Wintrust Arena.

Pro: Look Forward to Chicago Festivals

Those in the Windy City love to gather and have a ball, so plan to attend some of the best Chicago festivals! Celebrate with the Chicago St. Patrick’s Day Parade, dyeing the Chicago River green, and taking a cruise on that Irish-green water during St. Patrick’s Day in Chicago. Connect with the rhythm at the free Chicago Blues Festival and the diverse musician lineup at the Chicago Jazz Festival. Eat your fill of BBQ, watch the masters compete in contests including the “People’s Choice,” and listen to live indie music at Ribfest Chicago. Sample craft beer from breweries like Hop Butcher for the World at Ravenswood On Tap, or sip varieties of sauvignon blanc and chianti at the Lincoln Park Wine Festival. Chill out at a laid-back event with popular acts like Bon Iver, Mitski, and The Roots at Pitchfork Music Festival. Don’t miss seeing 170+ bands and musicians like past headliners Billie Eilish, Dua Lipa, and Maneskin perform on eight stages at the iconic Lollapalooza. Munch on dishes from over 35 of the city’s top restaurants and food trucks, and don’t forget to visit the wine garden at Taste of Chicago. Or score tickets to see fantastic films like recent favorites The Zone of Interest, The Whale, and Spencer compete at the Chicago International Film Festival.

Pro: Chicago is for Foodies

Drawing culinary experts from around the globe, Chicagoland is one of the ten best food cities in the country, so make sure to stop by some of Chicago’s top restaurants. Start your day with a Breakfast Sandwich or Chocolate Ganache Croissant with a cup of Kafe-Mansi at Kasama. Seek out pork dishes at The Purple Pig, seafood from RL Restaurant, or your choice of several options including vegan plates and tacos from Aster Hall, all located along the Magnificent Mile. Indulge in acclaimed, Chicago deep-dish pizza at local favorites like Pequod’s Pizza and Bartoli’s Pizzeria. Impress a date with a Cheese Plate, Tagliatelle, and Seasonal Gelato for dessert at Avec. Try a memorable, Chicago-style hot dog at well-known establishments like Redhot Ranch and Devil Dawgs. Make a reservation for Italian dishes like Burrata e Ham and Gnocchetti Con Pesto with a glass of red or white at Monteverde Restaurant & Pastificio. Or consider vegetarian recipes like Thai Basil Stir Fry or Buddha’s Karma Burger with a side of Yucca Chips at The Chicago Diner.

Pro: Never-Ending Chicago Nightlife

All the nightlife options in Chicago mean you won’t be bored any night of the week! Relish live blues music while enjoying burgers and sandwiches at Chicago blues clubs like Kingston Mines and Buddy Guy’s Legends. Join fellow music lovers for live local, national, and international jazz acts while sipping smooth drinks at Jazz Showcase and Andy’s Jazz Club & Restaurant. Be entertained by diverse bands and musicians, and get involved in events like open mic nights and Lip Sync for Life at Lincoln Hall and Schubas Tavern. Step in through the secret entrance to see acts by magicians while sipping a How Houdini Died or Misdirection at the Chicago Magic Lounge. Dance the night away or take a seat to vibe to live singers and bands amongst 1960s British invasion decor in The Bassment. Have vintage spirits downstairs in speakeasy-inspired The Office, then head upstairs for creative cocktails like the Jungle Bird at The Aviary. Or take a seat outside to relax with beer, wine, entrees, and shareable plates at some of Chicagoans’ favorite gastropubs, including The Gage and Hopleaf.

Cons of Living in Chicago

A post shared by @instagram

Just like any city, Chicagoland also has its faults. Check out these cons if you’re thinking about moving to Chicago.

Con: You’ll Pay a Bit More

It’s no secret that life in Chicago is expensive. The cost of living in Chicago is 14% higher than the national average, and you’re likely to pay more for groceries and healthcare than the rest of the state—including housing 43% more expensive than the Illinois average. But when taking into account Chicago’s population as the third-largest city in America, the Windy City is a more affordable big city to live. For example, Chicago’s cost of living at only 14% above than the national average is much more affordable than New York’s 69%, or LA’s 72% above the U.S. average cost of living. Not to mention, Chicago’s slightly inflated housing market is more accessible than Los Angeles’ home prices —which are a whopping 263% higher than the national average! So while a move to Chicago means paying more for certain things, it also offers access to world-famous museums, top-quality theatre, beloved sports teams, diversity, and so much more—making the costs well worth it for residents.

Con: Bitter Chicago Winters

Since the city is situated right on Lake Michigan, it experiences lake-effect snow, which often produces higher quantities of snow during likely times. The average yearly snowfall in Chicago is around 37 inches, especially compared to the nearby city of Indianapolis, which gets about 20 inches per year. Chicago’s climate is also very cold in the wintertime, with an average low of 22 degrees in January and 25 degrees in February. Even though surviving Chicago winters can be difficult, many locals say the summer makes it worth it! With average temperatures reaching an ideal 76 degrees in July and cool breezes rolling off Lake Michigan’s waves, Chicago residents can enjoy all the outdoor activities they like without much heat interference. And though Chicago is nicknamed the Windy City, it’s not any worse than the average metropolis—it doesn’t even make the top windiest cities in the U.S.!

Con: The Perception of Awful Crime

As a major metropolis, Chicago’s crime rates are 58% higher than the national average, with its share of organized crime and gun violence. Yet violent crime in Chicago is actually decreasing. Homicides declined 13% in 2023, and non-fatal shootings fell by 16%. Chicago isn’t even considered as one of the most dangerous cities in America by actual statistics, and cities with lower populations than Chicago—including Indianapolis and Detroit —have crime rates nearly doubled or tripled than the Windy City’s. This Midwestern city’s government programs for violence reduction also work with the local community to continue bringing Chicago’s crime down, including Street Outreach, Victim Services, and Neighborhood Activation.

Con: Congested Traffic

Unfortunately, Chicago has the worst traffic in America. If you’re in your car or a bus, you’ll lose a lot of time just sitting in Chicago traffic. To add to the problem, public transit is limited in suburbs, so many residents outside Chicago’s urban center need a car. Many of these professionals will commute to the city, part in a lot, and take public transit to work. As one of the cities with the best public transportation in the country, Chicago does offer commuter-friendly options, like the efficient Chicago Transit Authority (CTA). The Red Line runs north and south, and the Blue and Brown Lines take you east and west, with all lines converging in The Loop in Downtown Chicago. Additionally, the City of Chicago constantly works to improve the roads and sidewalks, maintaining its status as one of the nation’s most walkable cities.


If you’re considering relocating to Chicago, Life Storage offers storage units throughout the Windy City to make your move easier. Find cheap self storage in Chicago today!

About the Author

Life Storage

Rent storage near you at the right price. We'll show you what size storage unit you need, rent you a moving truck and more. We make self storage simple!

Pin It on Pinterest