Moving to Chicago Guide from a Chicagoan

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Chicago is More Than a Windy City 

From the shores of Lake Michigan to the boutique hotels of the Gold Coast, the vintage record stores of Avondale and Wicker Park, and the taquerias in Pilsen, the Second City is the premier cultural destination of the “third coast.” But as the third-largest city in the United States and the largest in the Land of Lincoln, an awful lot rests on the big shoulders of this Midwestern giant.  

With Chicago’s riverways, canals and the vast waters of the Great Lakes at its disposal, this early hub for transportation and trade became a beacon for immigrants and a primary point of connectivity for the globe, supplying lumber, grain and provisions from the Farm Belt to people all over the world. Economic, natural and manmade disasters have threatened the city’s very existence on several occasions, including the Great Chicago Fire in 1871, which claimed 300 lives and many of the city’s wooden buildings. But the resilience of the citizens and their determination to rebuild has made the city an architecturally rich wonder, from the Hancock building to Studio Gang’s alluring Aqua Tower.  

More than 2.7 million people now live in the city proper, and the Windy City’s sprawling suburbs from Aurora to Arlington Heights bring the metro population to 9.5 million. These Chicagoland residents are to thank for generating over $800 billion in GDP.  

But the rising cost of living in Chicago has driven some residents away — the population has declined since 2020 and has seen a net gain of only a thousand over the last ten years. The Second City is certainly not alone in this regard — New York City also suffered a mass exodus during the pandemic.  

One of the city’s stabilizing forces are its universities — The University of Chicago, the School of the Art Institute of Chicago and Northwestern University in nearby Evanston are three of the most competitive academic institutions in the U.S., and they, along with other area schools, provide a cultural and economic backbone for the city, especially in times of great transition. Time will tell whether Chicago’s ambitious redevelopment and investment plans will make city living tenable for its workforce.  

If a move to Chicago might be in your future, learn more about this vibrant, beloved city below to see if Chi-town might be the right place for you and your family.  

Living in Chicago

Be Ready for Brutal Winters 

Like a friend who always lets you know exactly how they’re feeling, Chicago’s weather never leaves anything to the imagination. The Windy City certainly can live up to its appellation, even though that moniker actually refers to its politicians being “full of hot air.” Being gray is the true Chicago way — the city averages only 45 completely sunny days a year. The rest of the time, you can expect the skies to be predictably moody.  

Lake Michigan is partly to blame for this mercurial weather. The lake effect can make areas around the third coast slightly warmer in winter and cooler in summer, but the moisture that stormfronts pick up over the water can bring piles of unexpected snow and cause storms to park themselves in the area for prolonged periods of time. 

Late spring and early fall (May-June and September-October) are pleasant times to be in Chicago — temperatures are usually mild and there is little threat of snow. The average low during these times is in the 40s Fand 50s Fand the average highs are in the 60s and 70s. The city receives a decent amount of rain throughout the year — roughly 37 inches annually — good news for gardeners.  

Chicago summers are usually warm during the day and cool at night: expect lows in the upper 50s F to low 60s F and highs in the low 80s. In this flat prairieland, you should always expect a few days of each month from May-September to break the 90-degree mark, and dramatic thunderstorms, hail and even tornadoes can accompany this hot weather.    

Winter is the opposite extreme. The average temperature in January is just 28 F, and windchills make the air bitterly cold. It’s a good thing there are so many great coffee shops and bars to warm up in. Chicago receives around 38 inches of snow a year, but the city has seen nearly 90 inches in a season. That was when the Blizzard of ’79 veritably buried the city up to its big shoulders, shutting down many transit lines and costing the mayor his job.   

Chicago’s Cost of Living is High

The cost of living in Chicago is high — housing, food and healthcare costs all surpass U.S. averages according to the Bureau of Labor Statistics. The unemployment rate in Chicago was 4.3% in March of 2023 — lower than it was a year ago, but still higher than the national rate.  

Next to other large coastal cities like Los Angeles or New York City, Chicago’s expenses pale in comparison, especially in housing. The median home value in Chi-town is $277,600, whereas the Big Apple’s is $660,700 and L.A.’s is an almost incomprehensible $705,900. The median household income in Chicago — $65,781 — isn’t much below these cities’ average incomes, either — your dollars will stretch farther in this Midwestern metropolis.  

One other potential deficit: At 2.05%, the state property tax is higher than most, and the Tax Foundation ranks Illinois in the bottom half of the nation for its business tax climate. If you plan on owning a home in the Windy City, you can learn about property taxes from Chicago’s Department of Finance and the Illinois Department of Revenue.  

Note: We are not tax experts and are not offering tax advice, other than you should consider obtaining additional information and advice from your legal and/or financial advisers who are fully aware of your individual circumstances. 

Chicago’s Economy and Job Market are Strong

Despite the higher cost of living in Chicago, there are lots of advantages to living in this lively city. One of the biggest is that Chicago’s economy and job market are strong and diverse. You won’t necessarily be locked into a single industry sector, if you move here. 35 Fortune 500 companies call Chicago home, and businesses from technology to finance, healthcare, design and life sciences thrive in the City of the Big Shoulders.  

Chicago grew to early prominence as a transportation hub, and its two airports, railways, riverways and highways — along with Lake Michigan — still support one of the biggest manufacturing, trade, distribution and logistics empires in the world. O’Hare alone is the country’s most valuable port. The city’s economy supports 4.7 million jobs, and its GDP is $833 billion — the third-largest in the nation.  

The city has its incredible universities to thank for the deep pool of talent in its workforce. Northwestern University, the School of the Art Institute of Chicago, the University of Chicago, Loyola, DePaul and Columbia College attract great students from all over the U.S. and train them for diverse fields and industries.  

Chicago has Good Public Transportation but Long Commute Time 

If you plan on commuting in Chicago, we have good news and bad news. The good news is that Chicago has a robust public transportation system. The bad news is that people still really love their cars here, and suburban sprawl is intense. This often leaves Chicago’s roadways snarled in traffic, which is the second-worst in the entire world. The average commuter has a 34-minute ride to look forward to each morning, but there are other ways to get to work in the Windy City than behind the wheel.  

The Chicago Transit Authority (CTA) manages a large fleet of buses and trains, including the “L” — a train elevated above the roadways — and the Metra, which transports commuters to the burbs, sometimes on cool double-decker cars. If you’re taking the L, a ride will set you back $2.50, buses cost $2.25 per ride, and students get greatly reduced rates on both. On the Metra, fares cost $6-$10. Daily and monthly passes can provide worthwhile savings. Parking in the city is astronomically expensive and sometimes difficult to come by, so using public transportation can save you a significant amount of money and frustration.  

If you’re looking to reduce your greenhouse emissions, there is a well-developed bike program and bike network in Chicago that will get you from point A to point B while soaking up some fresh air for yourself. The path around Lake Michigan is both picturesque and functional. If you’re wobbly on two wheels but comfortable on two feet, taking advantage of Chicago’s Pedway is a great way to stay out of the elements on uncooperative weather days.  

Flying in and out of Chicago couldn’t be much easier. Two airports serve the area, and both can be accessed from the city by train. Midway is the smaller venue, and the dedicated facility for Southwest. O’Hare is one of the busiest airports in the world, and its numerous carriers fly direct to many international destinations. 

Chicago Neighborhoods

If you’re new to Chicago, you’ll be delighted by the variety of neighborhoods that await you in this exciting Midwestern city. Chicago has long been a destination for immigrants, and you’ll find communities like Greektown, Ukrainian Village, Chinatown and Little Italy to be bastions of international culture, with great restaurants and shops as well as museums, libraries and educational centers. Housing costs in the Windy City can be steep but are still modest compared with other cities of its size. The median home value in the city is roughly $278,000 and the median gross rent costs $1,209 per month.  

Chicago’s financial district is centered in what’s known as The Loop — a busy, lakefront hub bound by the L encircling the area, which forms — you guessed it — a loop! This area also happens to contain some of the city’s crowning cultural jewels, like the Chicago Symphony Orchestra, Millennium Park, the Cultural Center of Chicago and Buckingham Fountain. Because this area is popular with tourists and residents alike, housing can be quite expensive, but young professionals favor it because of its walkability and proximity to their workplaces. Much of the architecture in this area is historic and well maintained, from the iconic Willis Tower (RIP, Sears!) to the Rookery Building, whose lobby was redesigned by Frank Lloyd Wright. 

Just across the Chicago River, the West Loop has a completely different downtown vibe. The warehouses of Chicago’s former meatpacking district have been converted into cool condos and apartments, with ground-floor restaurants and shops that beckon visitors with enchanting, atmospheric environments. Publican Quality Meats is a neighborhood butcher shop, market and café that heralds the district’s historic days, and it serves sandwiches that will make leave your carnivorous heart aflutter — be sure to try the Jambon Beurre. Solidifying the West Loop as the center of the food scene in Chicago is the Time Out Market, which was established in 2019 and brings an eclectic mix of the city’s finest to the table. With interesting galleries and boutiques, rents and home values in the West Loop are high, so the area is popular with an artsier professional set, who want to soak up the culture from morning till night.  

Printer’s Row is another historic center of Chicago, where bygone book-making centers have become airy lofts and businesses. This trendy area just a few blocks from Grant Park, is dotted with humbler haunts with a come-as-you-are attitude. The longstanding indie bookseller Sandmeyer’s still has its magnificent wood-floored retail space, which pays homage to the past while being a magical place to find bestsellers and the next great American novel. This business also participates in the popular Printers Row Lit Fest, which brings 100,000 visitors to the district each year for two days of immersive book nerdery — a favorite event in this very literary town that gave us the likes of Carl Sandburg, Gwendolyn Brooks and Saul Bellow.  

We encourage you to thoroughly research neighborhoods in the city to see which one has the right amenities, vibe and resources for your family, including the commute time, tax rates, cost of living, safety statistics and schools. 

Settle in and Explore Chicago

Few cities offer so many cultural treasures in such a welcoming and well-designed environment. Whether you’re looking to see the famous miniatures in the Thorne Room at the Art Institute of Chicago, learn about the Great Chicago Fire of 1871 at the Chicago History Museum or see a free performance of the Joffrey Ballet in Millennium Park, the Windy City is awash in wonder.  

Kids’ imaginations will be set free at the Chicago Children’s Museum, where they can build their own skyscraper or climb in the Cloud Buster. Want to immerse yourself in the natural world? Check out the 40-million-specimen collection of the Field Museum. 

Whatever the season, it’s always a good time to see a game in Chicago. Baseball fans have the White Sox and the Cubs to root for (or against, depending on if you’re a North-sider or a South-sider). There are Bulls games for basketballers and Bears games for football fans still nostalgic for 1986. The NHL’s Blackhawks draw huge crowds from around the region. The Chicago Fire — one of the city’s newest teams — are pitch-perfect competitors on Soldier Field. 

Want to get outdoors? Why not take a twilight paddle on a guided tour of the Chicago River? Or, how about a cruise on Lake Michigan on an authentic tall ship sailboat to see the Chicago skyline in a totally new light? Those who prefer landlubbing can still enjoy the water on wheels or heels — the 18-mile Lakefront Trail was designed for commuters and recreators alike. Or, explore one of Chicago’s many greenspaces, like Palmisano Park in Bridgeport, which has a fishing pond, restored wetlands and jogging trails.   

You’ll find even more of Chicago residents’ favorite haunts in our local guide to settling into Chicago. 

First-Rated Dining in the Second City 

If you’re looking for the best — and we mean the very best — hot dog in Chicago, don’t settle for anything less than super. Superdawg, that is. These caped, all-beef crusaders have been serving the citizens of Chi-town since 1948, and you’ll fall hard for their quirky packaging and signage and even harder for their dogs. These juicy links are adorned with a pickle spear, sport peppers, yellow mustard, classic Chicago green relish, chopped onions, the inexplicable Chicago tomato wedge and celery salt, then tucked into a tender poppyseed bud and nestled onto a bed of crisp crinkle Superfries™ that we’d almost take a nap in. Did we mention this place is also a drive-in? It’s almost too much joy to handle.  

Chicago’s pizza game has always been strong, but it’s now reached an almost ridiculous level of superiority. Deep dish pizza is one of Chicago’s culinary gifts to the planet, but you’ll find just as excellent Neapolitan pies in this Italian stronghold. Spacca Napoli in Lincoln Square is a perfect spot for a woodfired treat — get the Bianco di Stefano pizza with smoked mozzarella, black truffle pecorino, pancetta, rosemary and ricotta. We’re liable to start a feud if we pick favorites in the deep dish category, but if you twisted our arm, we’d have to go with the classic: Lou Malnati’s. There’s just something intoxicating about the aroma of the buttery crust and their sauce that will lure you in from blocks away. 

These comfort-food cornerstones are just the tip of Chicago’s culinary iceberg. South of the Loop in Chinatown, you’ll find some of the country’s best Chinese and Korean food. There’s no better place for dim sum than Ming Hin — the deep-fried crab and seaweed rolls, the barbeque pork buns, the shrimp crepes — it’s hard not to order one (or two) of everything on this extensive menu.  

In Chicago’s artsy Edgewater neighborhood, Little Bad Wolf is a cozy American gastropub with French, Mexican and Asian influences. The garbanzo-nopales tacos are delicious alongside the ginger-shrimp bao, but the triple-patty Wolf Burger with a fried egg and the famous, house-made onion straws will keep the hunger even the fiercest of beasts at bay.  

The Old Town neighborhood is home to The Second City, where many of the country’s biggest stars got their first big break, from Alan Alda to Tim Meadows to Tina Fey. After the show, have a bite at The Vig, a 50s sports parlor-themed pub with expertly prepared, almost-over-the-top, can-barely-bite-into-it sandwiches like the meatball sub, dripping with marinara, caramelized onions and three extra-melty cheeses, or the Mexicali vegan torta with jackfruit carnitas. 

How to Move to Chicago 

Let Mayflower’s team of trusted movers help you relocate to Chicago from anywhere in the U.S. Whether you’re moving long-distance or locally, Mayflower is here to simplify your move to Chicago. When you move with us, the Mayflower Move Portal will keep the information about your move streamlined and organized. 

If you’re moving cross country, Mayflower’s team of long-distance movers can move you to Chicago from anywhere in the United States. We offer full-service moving services and custom moving packages

Looking for local movers in Chicago? We can help! Mayflower’s Chicago Movers perform local moves in the state of Illinois independently under their own brands and business names.  

Moving to Chicago on your own? Mayflower provides professional resources for the DIY mover. Check out our moving checklists and packing tips

Curious about other cities in the Land of Lincoln? Check out our guide to moving to Illinois to learn more about popular suburbs and destinations across the state. 

Get a moving quote from Mayflower.  

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