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


Chicago is a great place to live for those who want a bustling urban hub without the cost or stress of a bigger city. Cleaner than New York and nicer than Los Angeles, Chicago is the largest city in the Midwest. As such, it still has a touch of humbleness in its roots. There is ample public transportation, good jobs and plenty of diversity. This makes moving to Chicago an attractive option for those looking to relocate. Despite not having access to a coast, the lakefront is a major part of city life. It offers a plethora of attractions and 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 relocating 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 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

The backbone of Chicago is in its 77 well-defined neighborhoods in nine districts — each with their own mix of attractions, culture, history, and personality. From Lincoln Square to Hyde Park, residents settle in and stay loyal to their own areas so choose where you lay down roots wisely.

  • North: Chicago’s Northern neighborhoods are youthful and desirable— from catching a Cubs game in Wrigleyville to boutique shopping in Bucktown and live jazz in Uptown, you’ll always have something to do.
  • West: The West Side offers a bit more of an eclectic vibe. Dine at ethnic restaurants and take in the stunning murals, monuments, and churches of Wicker Park.
  • Downtown: Downtown Chicago 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.

New resident tip: Chicago has a street numbering system which has evolved into one of the world’s simplest ways to get around. Here’s what you need to know.

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. When it comes to entry-level housing, Chicago offers the second-largest supply of starter homes. Zillow analyzed America’s 50 most populous metro areas to see which offer first-time buyers the best combination of affordability, availability, and rising median incomes.

The median home value in Chicago in 2018 is $228,500 and the median price of homes is currently $319,500. Plan on renting in Chicago? The median price for a home listing is $1,750 which is slightly over the national average, but much less than cities like Los Angeles ($3,650) and New York ($2,875). “If your goal is to slow down, buy a home and stay there for a while, this is a metro area where places are still affordable,” says Zillow economist Skylar Olsen. “Chicago offers first-time home buyers great inventory and good income growth.”

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

Moving to Chicago transportation tips

Chicago is a challenging city for work 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. 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.
  • Call a cab. Chicago taxis are plentiful and most accept credit and debit cards. In poor weather, try downloading Hailo to hail a cab with the touch of a screen!
  • Share a ride. Smartphone apps like Uber and Lyft hook you up with local drivers who will drop you off at your destination for a fraction of the price of a taxi. If you have time to spare and want to save even more dough, opt for their carpool option (Uber Pool or Lyft Line), which will pick up other passengers headed in the same direction.

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

Winter streets in Chicago

Owning a car is mostly unnecessary for navigating your everyday life if you’re moving to Chicago. If you happen to bring one, be prepared for No Parking signs, tow zones, and impossible parallel parking missions. Not only is parking expensive in the city (upwards of $30/hour is not uncommon downtown), 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. For those of you moving to Chicago, this means exactly what it sounds like.

“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 a nearby 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!

Read Also: How to Survive Winter in Chicago

6. …But winter isn’t the only season Chicago is known for.

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 over 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.

7. 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 26 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 the popular restaurant and bar, Castaways, North Avenue Beach offers volleyball courts, impressive views of the skyline, and great views for Chicago’s Air and Water Show. It’s one of the prime “see and be seen” spots in the city.
  • Oak Street Beach. Majestically framed by Chicago’s skyscrapers, Oak Street is downtown’s most accessible spot for sun and fun.

7. It’s extremely easy to meet new people.

Navy Pier in Chicago

It’s much more fun to explore the city with friends and Chicago makes it very easy to meet active, young professionals.

For the foodies:

If you’re moving to the food-centric Windy City, you’ll soon 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) and 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 over 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), Top Chef winner Stephanie Izard (Girl & The Goat, Little Goat), and Grant Achatz (Alinea, Next), who somehow managed to create 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 actually 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.

The bar scene in Chicago is immense with most spots open until 3 a.m. and some even 4 a.m. The trendier venues and clubs are typically in River North or Old Town, while the hipster dives can be found in Wicker Park. Wrigleyville and Lincoln Park are generally home to the more casual spots perfect for catching a game or sipping a beer on the patio. Speakeasies like Violet Hour are popular for a classy night out, while hotel rooftops are all the rage in summer.

For the shoppers:

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 WaterTower Place in the middle). Looking for something different? Here are a few other shopping destinations you’ll want to check out in Chicago:

  • Wrigleyville. For the best sports gear in the city, head to Wrigleyville—where you can find a Cubs, Blackhawks, Bulls, or Bears jersey.
  • 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.

For those looking to get active:

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

  • Explore on two wheels. The Lakefront Trail is Chicago’s original bike path, but the new 606 Trail is quickly gaining popularity. 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 Sports 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.

For the family:

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. The 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, but it’s already becoming 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. 1,000 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 those looking to get cultured:

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 the Museum of Science and Industry, The Art Institute of Chicago, the Field Museum, and the Adler Planetarium.

Looking to meet new people or make connections? Meetup groups offer something for everyone in Chicago — whether you’re a dog lover, political junkie, student-athlete or more. With hundreds of groups in the city, it’s likely that your crew is waiting for you to meet them.

Emerald green Chicago River for St. Patrick's Day

8. Chicago has some pretty weird-but-wonderful traditions.

If you’re moving to Chicago, you should keep the important traditions in mind.

  • St. Patrick’s Day — Every year on St. Patrick’s Day, 400,000 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 and dance are a long-lasting tradition “Chicago has this huge, rich musical history which, yes, blues, but also stepping, house music, which was born here in the ‘80s, and now juking music is popular with young South Side Chicagoans, and that’s made its way across the globe as well,” says Chicago Tribune writer and lifelong resident Brittany Julious.
  • 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.

9. You should learn to love your 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.

  • Cubs vs. White Sox. The Cubs finally broke the curse and as one of the most beloved teams in baseball, fans can’t wait for opening day at Wrigley Field, one of the oldest stadiums in the country. Beware of “The Crosstown Classic” — when the divide between the north and south side of Chicago rears its ugly head.
  • 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 Packers are in town.
  • Blackhawks. The Blackhawks have dominated the Chicago sports scene over the last few years, winning three Stanley Cups. And to think, it wasn’t that long ago when their home games weren’t even televised!
  • 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 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 from, chances are you could use some help storing your bigger, bulkier items. Life Storage offers self-storage options for anything you may not have room for in your home.

Update: This post was originally published on October 16, 2015, and was revised on August 25, 2019, with new information from Chicago expert, Lauren Monitz.

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About the Author

Lauren Monitz

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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