Moving to Chicago? Read on for tips from a local expert so you don’t walk into the Windy City unprepared.


Are you thinking about moving to Chicago? As the third-largest city in the U.S., Chicago is the ideal city for those who want to live in a world-class metropolitan area with Midwest values. Cleaner than New York and with a richer history than Los Angeles, the “Third-Coast” is a city full of culture, Michelin-starred restaurants, a world-class Central Business District and neighborhoods that are the backbone of the city’s colorful history. While many Chicago residents have roots going back several generations, Chicago welcomes new transplants with open arms.

Despite not having access to a coast, the Chicago lakefront is a major part of city life. With multiple beaches, waterfront restaurants, and an abundance of recreational activities, the lakefront offers a nice reprieve from the summer heat.

From towering skyscrapers to the rich cultural landscape, it’s easy to fall in love with the Windy City, but moving to Chicago requires more than just a trip down the expressway. The first thing to know is that it’s not called the Windy City because of the weather. While the lake effect is definitely real, the nickname comes from a longstanding history of corrupt politicians and the hot air they like the spew. But don’t let that deter you;the positives of living in Chicago far outweigh the negatives.

Whether you’re moving to Chicago with your family or venturing to a new city for a job, here’s some basic knowledge, so you don’t walk into the Windy City unprepared.

1. Your neighborhood in Chicago will actually define you.

Neighborhoods in Chicago

Chicago’s backbone is in its 77 well-defined neighborhoods in nine districts — each with its  own mix of attractions, culture, history and personality. From Lincoln Square to Hyde Park, each neighborhood becomes part of its resident’s identities.

  • North: Chicago’s Northern neighborhoods are youthful and desirable. 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 baseball game to catch.
  • West: The West Side offers a bit more of an eclectic vibe. Thanks to the West Loop’s Randolph Street and Fulton Market, the West Loop is considered the city’s culinary destination. Further west, you can take in the stunning murals, monuments and churches of Wicker Park.
  • The Loop: Chicago’s Loop is home to all the top tourist attractions: The “Bean” at Millennium Park, Buckingham Fountain, the Historic Theatre District, as well as art galleries, cocktail lounges and shopping on Michigan Avenue.
  • South: Chicago’s South Side boasts an array of cultural and social offerings. From monuments in Bronzeville to the Museum Campus in South Loop to Chinatown’s authentic cuisine, diversity runs deep.

2. Renting and home buying when you’re moving to Chicago is easier than you think.

House surrounded by trees in Chicago

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. 

“Compared to the East Coast and the West Coast, Chicago’s housing market is probably the best bargain in North America,” says Geoffrey J.D. Hewings, director of University of Illinois’ Real Economics Applications Laboratory. 

The median home value in Chicago in 2018 is $285,579. According to Zillow, Chicago home values have gone up 7.9% from January 2020 to February 2020. The median home price is currently $330,350.

Do you plan on renting in Chicago? The median price for a home listing is $1,635. While rental rates have gone down throughout the country, Chicago’s median rental cost is just $166 above the national average rent of $1,469.

3. Your transportation will probably consist of anything but a personal vehicle.

Moving to Chicago transportation tips

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.), but 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 L. 

The CTA offers a convenient system of buses and elevated trains known as the “L.” Trains are $2.50 per ride, and buses are $2.25. For complete convenience, get a Ventra card. You simply tap the card on the turnstile entrance and the fare is deducted from your account – no cash needed.

Choose the Pedway. 

The downtown pedestrian walkway, or Pedway, is a system of underground tunnels and overhead bridges that links more than 40 blocks in the Central Business District. It’s a safe, quick and convenient way to get around downtown (especially in the winter) and is used by thousands of commuters each day.

Opt to bike. 

Biking around town offers more flexibility (and definitely beats walking). Biking has become so popular in Chicago that a new bike-sharing company, Divvy, launched rental stations throughout the city.

Flag a cab or book a rideshare. 

Chicago taxis are plentiful, and most accept credit and debit cards. An alternative – and often more available option – is to book an Uber and Lyft ride from your smartphone.

Walk the lakefront. 

During the warmer months, you can walk the lakefront to get to destinations on the East side of the city. The Lakefront has multiple exit points, so you can easily walk from your Gold Coast apartment to your office in River North.

4. If you plan on bringing a car, be ready to call “dibs.”

Winter streets in Chicago

Owning a car isn’t entirely necessary for Chicago’s city life. If you happen to bring one and your home doesn’t come with a parking spot, be prepared for no parking signs, tow zones and impossible parallel parking missions. Not only is parking expensive in the city (upwards of $30 per hour is not uncommon), but you may also need a parking permit depending on where you live. Since the city is blessed with nearly 40-inches of snow each year, Chicagoans depend on street parking in neighborhoods where driveway space is limited. 

If you shovel a public parking space, residents think they’re entitled to that space — by saving it with lawn chairs, cones and whatever random backyard furniture they can find. This long-standing Chicago tradition is known as “dibs.”

“Herein lies the controversy of ‘parking dibs,’” notes Sara Boboltz, associate editor of the Huffington Post. “Some feel the inconvenience of clearing a spot on the curb grants them a license to call dibs, holding the space open with chairs and assorted debris while they’re not using it. Others feel this is downright selfish.” The polarized debate has been known to cause more than a few neighborly squabbles.

5. Chicago weather will heavily influence your wardrobe, commute and life.

Winter scene in Chicago

There’s nothing like the bone-chilling wind after it whips off the lake and bounces off a few skyscrapers. It gets cold in Chicago — very, very cold. So cold that Chicago-area schools have been known to close for cold days as much as snow days because it’s actually dangerous for students to go outside. Here are a few ways to prepare for those harsh, subzero winters:

Dress appropriately.

A heavy coat and a winter hat won’t be enough to prepare you for the lake effect snow (or the -10 degree wind chill). Make sure you have several layers of clothing and waterproof boots. Roads and sidewalks get slick and icy during Chicago winters, so always beware of the sneaky black ice.

Always have the emergency essentials on hand.

If you have a vehicle, make sure you’re always prepared. Keep jumper cables, a snow brush, gloves, shovels, water and provisions on hand at all times. Don’t forget your umbrella with wind vents, which will be necessary more often than not.

Don’t whine about it.

If you’re moving to Chicago, you simply have to learn to adapt to the climate. More weather complainers have moved to Chicago in the last few years, and natives are sick of the far-too-familiar monologue. Be prepared for the cold and embrace it!

Remember the 100 days of summer.

Summer is when everyone comes out of hibernation in full force. Festival season (May through October) means there’s a cultural excuse to party every weekend. With more than 150 events in total, almost every neighborhood puts on a local street fair celebrating their heritage, food and music scene. From the Randolph Street Market to Greekfest, Chicagoans love any excuse to be outside, drink and explore a new neighborhood.

Read Also: How to Survive Winter in Chicago

6. Embrace the beach scene.

Chicago skyline from the beach

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:

  • 31st Street Beach. Free of charge, you can’t compete with the beach’s painted trees to climb, a sprayground and spider-web rope structures for the kids. Grab some food from Pier 31 and listen to free live music on weekends.
  • Montrose Beach. For those with furry friends, Montrose Beach is one of the only beaches in the city to offer a designated dog-friendly zone. Elsewhere along the shore offers volleyball nets, kayaks, and cabana rentals.
  • North Avenue Beach. Just a short walk from Lincoln Park and home to Castaways, a go-to local restaurant. North Avenue Beach offers volleyball courts, impressive views of the skyline, and great views for Chicago’s Air and Water Show. 
  • Oak Street Beach. Majestically framed by Chicago’s skyscrapers, Oak Street is downtown’s most accessible spot for sun and fun. Oak Street Beach is home to Whispers, a waterfront restaurant perfect for people watching and soaking in Lake Michigan’s scenery.

7. There is no shortage of recreational activities.

Navy Pier in Chicago

Chicago has so much to explore, whether you’re adventuring solo, with friends or with your family in tow. Below outlines the nearly limitless activities that Chicago offers its residents.

Dining Destinations in Chicago

If you’re moving to the food-centric Windy City, you’ll grow accustomed to the three signature food groups: Italian beef, deep-dish pizza and the Chicago-style hot dog. Prepare for beloved beef sandwiches at Al’s Beef, the best deep-dish you’ve ever had at Pequod’s, Giordano’s, or Lou Malnati’s. (The actual best is a hotly debated topic and largely depends if you prefer your ‘za saucier or cheesier.) Or try a traditional Chicago-style dog from Portillo’s, which includes sport peppers and celery salt. And remember: in Chicago, ketchup on your hot dog is considered a sin.

But if you just want a great meal out, Chicago’s restaurant scene is one of the best in the country. With more than 8,000 restaurants, there’s a neighborhood or menu for virtually any palate. The West Loop is Chicago’s hottest dining district, so if you’re looking for a new favorite restaurant, that’s a good place to start. If you’re into ethnic gems, head to Chinatown for Asian delights, Argyle Street for Vietnamese, or Devon for Indian food.

Top Restaurants in Chicago

Chicago has a number of Michelin-starred restaurants and celebrity chefs, standout local stars being Rick Bayless for high-end Mexican cuisine (Topolobambo, Frontera Grill); Bravo’s Top Chef winner Stephanie Izard (Girl & The Goat, Little Goat); and Grant Achatz (Alinea, Next), a renowned chef managed who created one of the most impressive culinary legacies on the planet while battling tongue cancer. 

Alinea is one of the most awarded restaurants in the world and pioneered the concept of ticketed dining where you reserve and pre-pay for a meal based on a sliding scale based on date and time, much like a theater ticket. Other restaurants to seek out are anything from the Boka Group or Lettuce Entertain You.

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 (making sure to hit Water Tower Place in the middle). 

Looking for something different? Here are a few other shopping destinations you’ll want to check out in Chicago:

Oak Street

It’s not “the Gold Coast” for nothing! For those looking to drop some serious coin, Oak Street has long been a symbol of affluence for decades. Enjoy everything from high-end designers to local boutiques. But keep your eyes peeled – many shops are covertly tucked away into converted townhouses.

Wicker Park 

For those looking to exert their individuality, 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. It’s perfect for a day of window shopping.   

State Street 

State Street was Chicago’s first-ever shopping district. While Michigan Avenue is now the most prestigious area, State Street is still well worth the visit. You’ll find discount stores, hot lunch destinations and Macy’s at State Street – a local landmark and one of the largest department stores in the world. It even features the largest Tiffany’s glass mosaic dome in the U.S.

Athletic Activities in Chicago

While most assume Chicagoans hibernate in winter, they do get fairly active when the weather gets nice.

  • Explore on two wheels. While the lakefront trail is Chicago’s original bike path, 606 Trail is an excellent alternative for those who live further west. A 2.7-mile converted elevated railroad, it crosses Northside neighborhoods and has been revamped with green space and interactive art.
  • Kayak the river. 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.
  • Try whirlyball. Chicago’s signature team sport, Whirlyball is a cross between lacrosse and basketball… in bumper cars. It’s truly a memorable activity. 
  • Join a league. Chicago Sport and Social Club is 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 adventures to add to your list:

Navy Pier

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. Navy Pier was established to oversee the redevelopment of one of the most civic landmarks in the U.S. and is now one of the top-visited destinations of the world. Ride the rides, indulge in the tasty fair food or catch a boat tour.

Millennium Park

Construction of Millennium Park began less than 20 years ago, and it’s a huge part of the Chicago experience. Today, the 25-acre park contains some of the greatest public art pieces in the world, in addition to the Jay Pritzker Pavilion, Cloud Gate, Crown Fountain and Lurie Garden.

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 completely glass enclosure 1,353 in the air!

360 Chicago

Another view of the city for those not afraid of heights, the John Hancock Building also has an epic observation deck. One thousand feet above the ground, you can actually ride TILT, Chicago’s highest thrill ride – an enclosed moving platform that literally tilts you out over Michigan Avenue from the 94th Floor.

Lincoln Park Zoo

One of the oldest zoos in North America, it is also one of the last remaining free zoos in the country and 35-acres of animal fun.

For a Cultural Experience

While Chicago may be called the Second City, its cultural offerings are second to none.

  • Second City – 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 – One of the largest commercial touring hubs in the country, many popular productions have runs in Chicago. Check out their current schedule to see what’s playing, as shows and musicals rotate often.
  • Museums – It’s hard not to want to play tourist in Chicago with so 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 Museum of Science and Industry, 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.

8. Chicago has some pretty weird but wonderful traditions.

Emerald green Chicago River for St. Patrick's Day

Chicago’s traditions are the heart of the city and its residents. Some of the most beloved Chicago traditions include the following:

St. Patrick’s Day

Every year on St. Patrick’s Day, hundreds of thousands of spectators crowd the banks of the Chicago River to “ooh” and “aah” over its emerald green color. The dyeing of the Chicago River dates to 1962, when Mayor Richard J. Daley and Stephen M. Bailey, a childhood friend and then St. Patrick’s Day parade chairman, started the tradition. The event has become a huge attraction for both tourists and Chicago natives.

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 today by the Chicago Blues Fest; Jazz; Soul (Sam Cooke, Earth Wind & Fire and Jennifer Hudson call Chicago home); and so much more. Chicago is home to live music venues that are institutions, such as the Aragon Ballroom and The Vic Theater. It’s also home to cultural landmarks such as the Civic Opera House and the Symphony Center. Lastly, Ravinia, located just north of the city in Highland Park, is an outdoor concert venue that has live performances from artists ranging from James Taylor to Carrie Underwood, June through September.

Dance Music Festivals

Chicago has the most dance music festivals in the entire country due to its house music origin many decades ago, including the largest outdoor dancing series in the U.S., the nation’s premier free outdoor food festival, and the largest free blues festival in the world. Be sure to check out some of the upcoming events for this year, with Lollapalooza always being one of the standouts.

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 Marathon

The Bank of America Chicago Marathon is one of the six World Marathon Majors. Held annually in October, the 26.2 mile race spans 29 Chicago neighborhoods.

9. You should learn to love Chicago sports.

From the major sporting franchises to its die-hard fans, Chicago loves its sports teams. 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 teams. No matter which team you root for, sports are a fun and competitive way to enjoy time with friends and family.

  • Chicago Cubs vs. Chicago White Sox – Chicago residents are either north side Cubs fans or south side Sox fans – there is no in-between! “The Crosstown Classic” — when the divide between the north and south side of Chicago rears its ugly head.
  • Chicago Bears – Chicago fans love showing their football fandom at Soldier Field (and keeping the spirit of former head coach Mike Ditka, now a national TV personality, local legend and successful restauranteur, alive), especially when rivals like the Green Bay Packers are in town.
  • Chicago Blackhawks – The Blackhawks have dominated the Chicago sports scene, winning three Stanley Cups in recent years. And to think, it wasn’t that long ago when their home games weren’t even televised!
  • Chicago Bulls – The ‘90s Bulls were one of the most dominating dynasties in professional sports, and while the Michael Jordan, Scottie Pippen, Dennis Rodman era may feel like a thing of the past, it’s still fun to reminisce on the glory years.

Are you ready to make your move?

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 self-storage units in Chicago for anything you may not have room for in your home.


  • 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.

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About the Authors

Deanna Kane

Deanna Kane is a life-long Chicago-area resident and writer with a Bachelor of Arts In Communication from the University of Iowa. For 15 years, she has been writing about both local and national real estate, home design and interiors, as well as restaurants and family-friendly destinations in both the city of Chicago and surrounding areas. She's explored nearly every Chicago neighborhood on foot having run three Chicago Marathons herself. When she isn't exploring the city by running, she is exploring the ever-evolving neighborhood restaurants, boutiques and farmers’ markets.

Lauren Monitz

Lauren Monitz is a travel writer living in Denver, CO. Originally from Chicago, IL, she has first-hand experience with moving to Denver. Lauren is a graduate of the University of Colorado and earned her master’s degree from DePaul University. She covers all of her adventures on her personal blog, TheDownLo, and has over 195k social media followers.

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