Are you thinking about moving to Chicago? The third-largest city in the U.S., Chicago, is the ideal city for people who want to live in a world-class city with Midwest values. The Windy City offers more than its fair share of culture, Michelin-starred restaurants, world-class business districts, and neighborhoods that are its true character.

Despite not having access to the coast like its urban rivals, New York and Los Angeles, the Chicago lakefront is a significant part of city life. With numerous beaches, waterfront restaurants, and an abundance of recreational activities, the lakefront offers a nice reprieve from the summer heat.

With its spectacular skyline and architecture, it’s easy to fall in love with the Windy City, but moving to Chicago requires more than just a trip down the expressway. You have to get off a few exits before downtown and merge into its unique culture! It truly is the “Third Coast.”

The Many Neighborhoods in Chicago

The bulk of Chicago’s scene surrounds the downtown areas of River North and the Loop. Chicago’s 77 different neighborhoods offer their own unique flair of attractions, culture, and history. Where you choose to live in Chicago will define your every day.

North Side: Chicago’s North Side neighborhoods are a mix of young college students, professionals, and families. From catching a Cubs game in Wrigleyville to boutique shopping in Lincoln Park and live jazz in Uptown, there is always a concert, street fest, or sports game to catch.
West Side: The West Side offers more of an eclectic vibe. Thanks to Randolph Street’s Restaurant Row, the West Loop is considered the city’s culinary destination. Further northwest, you can take in the stunning murals, monuments, and churches of Wicker Park and Logan Square.
Downtown- River North/The Loop: Chicago’s downtown area is home to all the top tourist attractions: The “Bean” at Millennium Park, Chicago’s Art Institute, the theater district, art galleries, cocktail lounges, and shopping on Michigan Avenue.
South Side: Chicago’s South Side boasts an array of cultural and social offerings. From the urban gothic architecture of Hyde Park’s University of Chicago to the Sox Park in Bronzeville, the whole area is an eclectic mix of arts, education, sports, and more.

Jobs, Housing, and Other Responsible Things

Chicago’s Job Market

With Chicago being one of the largest cities in the country, the workforce is extremely diversified – not one sector commands more than 14% of the population’s careers. It is a continually growing major metropolitan area, according to Tom Shallcross of StrightUp Chicago Investor, stating, “fifty new companies moved to Chicago over the past year, seventy other companies expanded their existing footprint, with twenty of those seventy residing in the South or West side.”

Chicago’s job market is robust- always in search of top talent. High-paying positions are in high demand. Marketing jobs in Chicago, in particular, are a popular career in the industries of sports entertainment, tech companies, startups, and major corporations like Morningstar, United, and Boeing. To secure highly sought careers, the best tactics in Chicago employment are networking with field-specific associations, applying online directly with the company or utilizing a recruiter, and taking these handy hints from builtinchicago.org.

Chicago Housing Market Trends

Whether you’re looking for a single, temporary apartment or moving your family into a forever home, now is a good time to rent and buy in Chicago. How much money do you need to move to Chicago? The median home value in Chicago in 2022 is $309,268. According to Zillow, Chicago home values have increased 9.1% from January 2021 to February 2022. The median home price is currently $320,000, according to NORADA – up from 2021 by 7.9%. Plan on renting in Chicago? According to Zumper, the median price for a one-bedroom is $1,600.

Chicago Taxes

Property taxes in Chicago are increasing almost annually. Cook County has an effective tax rate of 2.52% – the second highest in the state. These rates are placed on the property’s assessment value, not the market value. Sales taxes are on the higher end of the 7.3% national average at 10.3%, with additional leisure taxes on sugar, bottled water, liquor, and cigarettes. Sales taxes are set at 5%, 4% higher than most states.

What’s the Ideal Living Wage in Chicago?

Monthly expenses like grocery shopping (average cart price of $60), utilities (Including internet, natural gas, and internet- $220), transportation (depending on the use of mass transit or personal vehicle- $150 to $600), and entertainment ($300-$1000) are all about median rates. How much does it cost to live in Chicago per month? The cost of living in Chicago is average compared to the rest of the United States, according to Numbeo.

Is it expensive to live in Chicago? According to AJ Latrace, Chicago Real Estate Analyst, “With an inflation rate of over 5%, the value of money is decreasing at a faster rate than normal, thus key consumer costs and indexes on items like housing and food.” If you are renting, the typical income requirement is 30% of your monthly salary needed to be dedicated to your housing costs, according to ApartmentList. Using this formula, you need to make around $65,000 to live comfortably in a 1-bedroom unit. If purchasing a home is in the cards, there are quite a few things to consider. What salary do you need to live in Chicago? Between the mortgage rates and the typical down payment of 20%, per HSH, the average homeowner should be making about $73,000 annually to ensure mortgage payments, home repairs, and property taxes are affordable.

Retiring in Chicago

Retirement housing in Chicago might not sound like the typical plan for a pensioner, but it does have its allures. Most older Chicagoans are snowbirds – flocking to the warmer states of Arizona, Florida, or California when the polar vortexes hit. But Chicago is a great place to lay your hat when you finally retire. Chicago’s average retirement age is about 64 years old, and the project comfortable retirement income is $54,657.

But why stay when there are so many benefits to moving South? First, the city has a lot of activities to fill your free time – you haven’t kicked the bucket yet, you know! Family is another reason people choose to stay, so moving to Chicago because of your family might be the main factor for you.

The hospitals in the city are unparalleled with Northwestern University, Rush, Advocate, and the University of Chicago all boasting state-of-the-art medical campuses within the city.

Many people can’t leave once they’ve moved to Chicago. It’s a city where love lasts a lifetime.

Chicago Schools, Colleges, and Universities

Chicago Public Schools

The Chicago Public School system has some great schools with focused educational programs and award-winning staff. Some notable Chicago schools include:

Waters Elementary in Lincoln Square takes a holistic approach to learning with a large community garden, where students get hands-on experience in ecology.
Poe Elementary, located at the very southern tip of the city, just received the 2021 Thrive Award, recognizing amazing achievement in test scores, reading level, and elevated math skills.
Lane Tech High School is located just outside of Roscoe Village. Many talented Chicagoans attend this high school, known for its heightened academics and extensive athletic department.
Walter Payton College Prep is named after the famous Chicago Bears player. This college prep school in New City has fast become a school that everyone is trying hard to get into.

Chicago Private Schools

Despite all the goodness of Chicago Public Schools, there are private options.

The Waldorf School focuses on incorporating art into all fields of study.
The Latin School, Montessori utilizes hands-on and immersive learning experiences from pre-kindergarten to 8th grade.
The Chicago Archdiocese is a network of Catholic schools offering a robust spiritual and diverse education.

Chicago Colleges and Universities

Chicago is home to many renowned universities. From the arts at The School of the Art Institute of Chicago and Columbia College and the music department of Roosevelt University, there is a degree for everyone. There are even smaller liberal arts campuses like North Park University and St. Xavier University. But, most notably, are these campuses:

City Colleges of Chicago is a network of community colleges great for high school graduates starting their higher education journey and adults taking continuing education classes. There are seven locations throughout the city.
Northwestern University has its main campus, featuring Bachelor’s, Master and Doctorate programs, just north of Chicago in Evanston. There is also a medical and law-focused campus in Chicago’s River North neighborhood.
DePaul University is a famous university with two campuses. The Lincoln Park Campus focuses on liberal arts, science education, and Music. The Loop location houses schools for communication, law, and business. They are connected by a college-run bus and the CTA Red Line.
Loyola University is a Jesuit college whose name is recognized around the country. There are over six campuses across the city and highly specialize in many different schools, including medicine, law, science, and the fine arts.
University of Chicago is the Ivy League university of the Midwest. This educational facility was established in 1890 and has an elaborate campus boasting a comprehensive hospital, state-of-the-art research facilities, and a couple of museums that are renowned and open to the public.

Chicago Transportation – From the Car to the Train

Chicago is a challenging city for daily commuters with some aggravatingly long rush hours (6:30 a.m. to 10:30 a.m. and 3:30 p.m. to 7:30 p.m.). Still, there’s good news: the Chicago Transit Authority, or CTA, can get you to just about every corner of the city, including some adjacent suburbs. You have plenty of options when it comes to transit:

Take the Bus or the L – Chicago’s public transportation option, the CTA, offers a convenient system of buses and elevated trains known as the “L.” Trains and buses are $2.25 with a free transfer. For complete convenience, get a Ventra card. You tap the card on the turnstile entrance, and the fare is deducted from your account – no cash needed.
Get a bit farther with Metra – With a slogan, “The Way to Really Fly,” they aren’t kidding. This regional train system will get you to Wisconsin or Indiana far quicker than driving on the expressway. But more importantly, these lines connect the city to the rest of Chicagoland for pretty fair rates, including weekend passes.
Opt to bike- Biking around town offers more flexibility (and beats walking). Biking has become so popular in Chicago that a bike-sharing company, Divvy, launched rental stations throughout the city.
Driving Around- Despite all the transportation options, driving in Chicago is a convenient way to get around, considering it’s a big city. WIth a grid network of streets, connected with diagonal avenues, it’s easy to find shortcuts. The highway system is also a convenient web of thoroughfares connecting all of Chicagoland easily.

Dining in Chicago

If you’re moving to the food-centric Windy City, you’ll grow accustomed to the three signature food groups: Italian beef from Al’s Beef, deep-dish pizza from whichever is your favorite (Lou Malnati’s, Giordano’s, Rosati’s…) and the Chicago-style hot dog (some say Portillo’s but do yourself a favor and go to Red Hot Ranch) – remember, ketchup is a sin.

Chicago’s Food Scene is No Joke

Chicago’s restaurant scene is one of the best in the country. With more than 8,000 restaurants, there’s a menu for even the pickiest eaters. Chicago’s top restaurants are Michelin-starred restaurants, found along the Chicago Riverwalk and in the air on Chicago’s rooftops.

Every ethnicity is represented, but Chicago does have some of the best Italian restaurants this side of Sicily. Little Italy is renowned as Chicago’s Italian restaurant epi-center with mainstays like Tuscany, Tufano’s, and Rosebud. Some great restaurant groups to seek out are anything from the Boka Group or Lettuce Entertain You.

Chicago Vegan Restaurants

The Chicago Restaurant scene would be incomplete without its collection of delicious vegan options. With health-conscious dining on the rise, Chicago has some of the best options in any big city.

Kale my Name – This off-the-beaten-path all-vegan spot has been voted the best vegan restaurant in the country by VegNews and offers up fully vegan-friendly options and gluten-free, with a side dish of craft cocktails.
The Chicago Diner – One of the oldest Chicago vegan restaurants, opening in 1983, this diner (in two locations in the city) provides inventive dishes at modest prices, using locally sourced ingredients.
Alice & Friend’s Vegan Restaurant- This pan-Asian vegan restaurant serves up plant-based burgers, veggie chow mein, and homemade desserts. The best part is it is BYOB, too!
Chicago Raw Food – This newer edition to the Chicago vegan restaurant scene focuses more on raw vegetables with salads, smoothies, and plant-based edibles.

A Table with a View

With all the skyscrapers, the options for dining in rooftop restaurants in Chicago are endless. Here is a curated selection of clubs and restaurants that offer flawless views of the city:

Cindy’s – This rooftop bar and restaurant is right on Michigan Avenue and faces the beauty of Millenium Park. It is also attached to the amazingly ornate Chicago Athletic Association, so perfect place to go if your family or friends are in town visiting.
The Signature Room – This classic mainstay of views and fancy lounges is at the top of the John Hancock Building. On the 95th floor, the views of the cityscape and the lake are unparalleled.
City Mouse – At the ACE Hotel in the West Loop, this youthful funky bar has a unique view of the city from the west. DJs play, game nights are had, and it’s always fun!

An Old Fashioned, Please

With Chicago’s rich history, it would be a boring town without a few historic bars to haunt. Luckily, Chicago has them in surplus. Here are a few of our favorites:

Green Door Tavern- One of the oldest bars in Chicago, this eclectically decorated bar has a mystery shot lottery, a maze of rooms, and a secret speakeasy that’s accessible if you ask the bartender how to get there.
Old Town Ale House- If you are looking for America’s next comedian, this is your spot. Just across the street from the Second City campus, this bar plays host to all the young up-and-coming funny people just getting out of class. Look for all the alumni photos if you don’t believe us!
Pippin’s Tavern- Located in the thick of the Magnificent Mile, this historic Chicago bar has been a part of many people’s lives. From hospitality industry staff to Fortune 500 level CEOs, the bar stools have seen it all.
Simon’s Tavern- This Andersonville bar is said to be haunted by the old owner, frightening the rowdy bar patron. If you are looking for a classic dive bar in Chicago, this is a sure bet.

Chicago Activities: From the Lake to the Museum…

Embrace the Beach Scene

While many out-of-towners don’t think of the Midwest as a beach destination, the Great Lakes are just that… great! Chicago offers 18.5 miles of sand along Lake Michigan and an impressive summer beach scene sans saltwater. Here are some must-see beaches in Chicago.

Montrose Beach is one of the only beaches in the city to offer a designated dog-friendly zone.
North Avenue Beach offers volleyball courts, impressive skyline views, and great views of Chicago’s Air and Water Show.
Oak Street Beach, framed by Chicago’s skyscrapers, is downtown’s most accessible spot for sun and fun.

Shopping Destinations in Chicago

The Second City has some serious style and is arguably a first-rate shopping destination. Michigan Avenue features a mile-long stretch of tucked-away boutiques, restaurants, and high-rise malls. For the ultimate “Magnificent Mile” shopping experience, begin at one end of North Michigan Avenue and make your way to the other.

If you’re looking for something different, here are a few other shopping destinations you’ll want to check out in Chicago:

Oak Street – For those looking to drop some serious coin, Oak Street has long been a symbol of affluence. Enjoy everything from high-end designers to local boutiques.
Wicker Park – Wicker Park has the majority of thrift stores and independent labels. Don’t miss Akira, one of Chicago’s trendiest and most affordable local brands.
State Street – State Street was Chicago’s first-ever shopping district. You’ll find Macy’s on State Street – a local landmark and one of the largest department stores in the world.

Athletic Activities in Chicago

Once the polar vortexes retreat back to the Arctic Circle, and the tulips pop up throughout the city, Chicago transforms into an active place! The lake, river, and prairie provide some of the best landscapes for recreational activity.

Biking – Chicago is such a bike-friendly city. While the lakefront trail is Chicago’s original bike path, 606 Trail is a 2.7-mile converted elevated railroad. The North Branch Trail crosses Northside neighborhoods and provides a touch of nature as it runs alongside the Chicago River.
Kayaking – Is there anything cooler than paddling amongst skyscrapers? A variety of downtown kayak tours are offered to give a lay of the land. These cover the city’s architecture and history, ghosts and gangsters, and sunrise and sunset.
Intramural Sports – Chicago Sport and Social Clubs are one of the best ways to meet people and get a workout. Beach volleyball is a popular sport, along with co-ed kickball and Chicago’s signature 16” softball.

Family Activities in Chicago

If you’re looking for things to do with your family in Chicago, you don’t have to look far. Here are some of the best kids’ activities in Chicago to add to your list (the adults will have fun, too!):

Navy Pier has been a Chicago landmark since the days of the World’s Fair. The 3,300-foot-long pier offers a 50-acre playground, 150-foot Ferris wheel, and excellent views of the city right on the shoreline of Lake Michigan. The pier is also home to the Chicago Shakespeare Theater and the Chicago Children’s Museum.
Millennium Park is a huge part of the Chicago experience. Today, the 25-acre park contains the Pritzker Pavilion (offering live music almost every day in the summer), The Bean, and Lurie Garden. Maggie Daley Park is also adjacent with winding paths, a large playground, a rock climbing wall, and a mini-golf course – all with the skyscrapers looming over you.
Willis Tower, formerly known as the Sears Tower, the 110-story building is the second tallest building in the U.S. While it’s one of Chicago’s most popular tourist destinations, you’ll want to check this one out. The Ledge at the Skydeck offers spectacular views in a glass enclosure, 1,353 feet in the air! Pro-tip: Everyone still calls it the Sears Tower.
Lincoln Park Zoo is one of the oldest zoos in North America. It is also one of the last remaining free zoos in the country and has 35 acres of animal fun. The Peggy Notebaert Nature Museum is just across the street, where the whole family can learn about the city’s ecology – from pigeons and cardinals to worms and fish!

Chicago Culture

While Chicago may be called the Second City, its cultural offerings are second to none. Check out these other fun Chicago activities of the cultural variety:

Second City is Chicago’s first improv troupe and the world’s premier comedy club. Many famous comedians have gotten their start at Second City. Catch a nightly live show and laugh until your sides hurt.
Broadway in Chicago is one of the largest commercial touring hubs in the country, where many popular productions have run. Check out their current schedule to see what’s playing, as shows and musicals rotate often.
Museums in Chicago. It’s hard not to want to play tourist in Chicago, with many world-renowned museums for art, history, and nature lovers. Pay a visit to Chicago’s Museum Campus to make a day of visiting the Shedd Aquarium, the Field Museum, and the Adler Planetarium. The Art Institute of Chicago is in the Loop, and the Chicago History Museum is further north, in Lincoln Park.

Chicago Sports: We Got Them All – College and Pro!

It’s in your best interest to become a loyal and passionate fan (or at least pretend to be), rooting for one of Chicago’s many professional and college teams. Whether you are sitting in the stands at an arena or one of the many Chicago sports bars, Chicago’s sports teams are a fun and competitive way to enjoy time with friends and family.

Chicago Cubs – This beloved baseball team used to be known as the lovable losers who played in the friendly confines until 2016 when history turned in their favor.
Chicago White Sox – The more rough-and-tumble major league baseball team of Chicago, this team has its die-hard fans and one of the best parks.
Chicago Bears – Chicago fans love showing their football fandom at Soldier Field (and keeping the spirit of former head coach Mike Ditka), especially when rivals like the Green Bay Packers are in town.
Chicago Blackhawks – The Blackhawks have dominated the national hockey scene, winning three Stanley Cups in recent years. Their loud and boisterous fan base encompasses the entire city.
Chicago Bulls – The ‘90s Bulls were one of the most dominating basketball dynasties in professional sports, and while the Michael Jordan, Scottie Pippen, Dennis Rodman era. Chicagoans know this team will rise again!
Chicago Sky – The WNBA team won the championships in 2020, and while it didn’t deserve the fanfare it deserved, they did their hometown good!
Chicago Fire – Soccer is becoming a fast favorite in the states, and the Chicago Fire doesn’t disappoint as one of the best USMNT teams in the country.

Other Fun Chicago Activities

Emerald green Chicago River for St. Patrick's Day

Chicago has some weird and wonderful traditions that live in the city’s and its residents’ hearts. Whether you want to stay and cozy up indoors to some live music or check out Chicago’s wild outdoors, the most beloved Chicago activities include:

Chicago St. Patrick’s Day

Every year on St. Patrick’s Day, thousands crowd the banks of the Chicago River to marvel at its emerald green color. The dyeing of the Chicago River dates to 1962 when Mayor Richard J. Daley started the tradition. The event has become a huge attraction for tourists and Chicago natives, becoming one of its most famous outdoor activities to date.

Chicago Air and Water Show

The Chicago Air and Water Show is the oldest and largest free air and water exhibition. It started in 1959 and features military and pilots performing awe-inspiring stunts over Lake Michigan.

Chicago’s Musical History

In Chicago, music is a long-standing tradition. Chicago is known for its history of Blues music, which is still honored at the Chicago Blues Fest. Buddy Guy’s for a show, anyone? Chicago (the band), Smashing Pumpkins, Wilco, and Fallout Boy got their start in famous Chicago music venues like Aragon Ballroom, the Metro, and the Hideout. However, you cannot miss going to the Green Mill, which boasts musical, Prohibition, and gangster history all rolled into one jazz club. A cocktail and a live gig on a cold night are among the best Chicago indoor activities.

Music Festivals

Chicago has its fair share of open-air music festivals that take place throughout the city. The best part is they are all accessible by Chicago’s public transportation system, so you can have all the fun want there without the hassle of parking!

Lollapalooza – One of the original large-scale music festivals, this Grant Park mega-event hosts a variety of musical artists and bumps the whole city.
Riot Fest – The punk rock version of Lolla, this Douglas Park event brings in international rock outfits for a mad good time.
Spring Awakening – Electronic dance music (EDM) got hot in recent years, and this festival is the epitome of trance dance.
Pitchfork – If indie is your jam, this festival held in Union Park is the premier event for you. Catch well-known acts or the next big thing!
North Coast – This second EDM festival of the year is known as Summer’s Last Stand, as it is held over Labor Day and bookends Chicago’s warm season with trance.

LGBTQ+ Chicago

Chicago’s LGBTQ+ community is such an inclusive and inviting one, that there is no real divide in the city. The Windy City is entrenched in the civil rights history of LGBTQ+.

So, is Chicago LGBTQ-friendly? According to Jessica Herczeg-Konecny in LGBTQ America, “Cities like Chicago provided space for people to explore different expressions of sexuality and gender identity, freer from familial or religious oversight. The city allowed for increased anonymity and enabled people to find each other, come together, and develop communities of people like themselves.”

At the forefront of public inclusion in the late 20th century, one of the first PRIDE parades was held in Chicago in 1970, just before the first anniversary of the Stonewall riots. Abbott Technologies, based in Illinois, developed the first HIV blood test. The Windy City continues to be a safe harbor, steady home, and swinging hotspot for the LGBTQ+ community.

Where to Hang in LGBTQ+ Chicago

Almost all Chicago neighborhoods are LGBTQ+ friendly, but there are a few hotspots where the pride really shows.

North Halsted – Just east of the boisterous Wrigleyville, this was Chicago’s first gay neighborhood – originally called Boystown. From the suggestive dance floors to the comfort of boutiques and specialty shops, this stretch of North Halsted Street is always a fun time.
Andersonville – Also on the northside of the city, this Swedish community has become home to many older members of the LGBTQ+ community. A bit more subdued than North Halsted, there is a strong community here, minded towards inclusiveness and awareness.
Howard Brown Health Center – This public health center focuses almost solely on the LGBTQ+ population of Chicago. Their programs offer free testing, mental health support, and financial assistance to underserved community members. They are a true force of good in Chicago.
Northalsted Market Days – The party truly never stops in Northalsted. Members of the community take to the streets the whole summer and Market Days is one of the best Chicago events of the season.
Chicago PRIDE Fest – So here’s the thing about PRIDE in Chicago – we take it seriously. So seriously that it is a two-week-long celebration of self, love, and fun! Chicago’s LGBTQ+ population has mastered the hurrah of PRIDE with one weekend dedicated to the festivities, and one weekend for the long-awaited annual parade. With all the colors, the music, and the fashion, it is never to be missed.

Start Your New Life Living in Chicago

Whether you’re moving to Chicago for business, relocating with your family, or looking for an adventure in a brand-new city, it’s easy to fall in love with Chicago. Submerse in the culture, explore the diversity and figure out your favorite authentic Chicago spots in no time.

No matter where you’re moving to Chicago from, chances are you could use some help storing your bigger, bulkier items. Life Storage offers cheap storage units in Chicago for anything you may not have room for in your home.

Updates:

Revised July 28th, 2022, with new information from Chicago expert, Caitlin Meeter.
Revised on April 21, 2021, with new information from Chicago expert, Deanna Kane.
Revised on August 25, 2019, with new information from Chicago expert, Lauren Monitz.
Originally published on October 16, 2015.

Pin for later:

Making the Big Move to Chicago? Check Out These Tips from a Professional Chicagoan!

The Many Neighborhoods in Chicago