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The Ultimate Guide to Living in Chicago

Living in Chicago for the first time? We've got you covered!

If this will be your first time living in Chicago, this guide will get you acquainted with your new home — one of the best cities in the world.

You’ve arrived. Welcome to the the third-largest city in the U.S., the Mecca of the Midwest, Da Home of Da Bears, and the Second City. Whatever you call it, it’s a town that’s a bustling center of culture, sports, business, shopping, beaches and parks, restaurants and bars, history and people from all walks of life — a melting pot that doesn’t rely on one culture to define it.

Bottom line, you're going to love living in Chicago.

living in chicago

Source: Giphy

Introduction to Chicago and this guide.

Although it literally burned to the ground in 1871, it continues to smoulder with a rich art and music scene, culture and traditions from all corners of the globe and the city hustle that makes it one of the most attractive places to work and live. You can choose to find out what makes the city unique, but ultimately this city is now yours. And now it’s time to explore. 

Whether Chicago will be your first big city or you're arriving from another metropolis, Chicago can be a bit daunting at first. It boasts dozens of different and unique neighborhoods, each bringing something to the overall makeup of what it means to be a Chicagoan, and with so many options for where to live in Chicago, you’ll have the fear of missing out on the best area in the city; that "neighborhood that beats all others." 

Though this writer — and every dedicated Chicagoan — could tell you, it’s hard to sum up a neighborhood in a few hundred words. We’ll highlight some neighborhoods on all sides of The Loop (Chicago’s downtown) but remember: you can access any part of this city with ease. Later, we’ll dive how you can get around the city, even without a car, but for now, a look into some of the neighborhoods in Chicago. 

living in chicago

Source: smartbizstartup.com

Living in Chicago: Neighborhoods

Residents in Chicago are proud to live in the city, but they’re even more proud to tell what makes their neighborhood the the crown champion of Chicago, the best of the bunch, the gem where all others should be jealous to live. Once you live here, you’ll know what everyone has been talking about. 

We can’t take you through all the neighborhoods here, but we’ll start in the north neighborhoods and work our way counterclockwise to the west side and down to the South Loop

Neighborhoods north of The Loop.

Chicago’s Old Town and Lincoln Park are known for their iconic walkup brownstones that a trademark to upscale and eclectic neighborhood blocks. The historic Lincoln Park is the biggest park in the city, and Lincoln Park Zoo, which is free, is a favorite every day of the week, providing views of the lake to the east and skyscrapers to the north, as well as a scenic path for runners, walkers, bikers and boarders alike. Within walking distance is the Chicago History Museum, the historic Apollo Theater, and Kingston Mines, arguably the best live jazz venue in the city (at the very least, one that boasts great late-night hours), Lincoln Park is your entrance from The Loop into the neighborhoods of the northside. 

Upscale bistros and bars, boutiques and bakeries are abound in Old Town. Want a neighborhood bar that’s got an old-time wood finishes and great food? Twin Anchors Restaurant and Tavern was a favorite of Frank Sinatra, the Blues Brothers and Two-Face from The Dark Knight Rises, and there’s little doubt you’ll be doing an about-face on any barbeque you’ve ever tasted. 

Stanley’s Tap and Grill, a restaurant and bar where Cubs players did karaoke after a recent win, is in the Old Town Triangle; world-renowned food experiment Alinea off Halstead is incredibly hard to get into, but a once-in-a-lifetime experience; hard-to-find Interurban Cafe & Pastry Shop is worth the asking someone on the street where it is; and a deep-dish favorite that’s different than Chicago chains, Pequod's Pizza, is right on the corner of Clybourn. (You’ll see the line outside for people waiting for a table.) 

A great shot of Chicago's Lincoln Park.

living in chicago

Source: wikimedia.org

Northwest Chicago

Now to Logan Square. One of the more culturally-diverse neighborhoods on Chicago’s west side, while remaining one of the most up-and-coming neighborhoods in terms of gentrification, Logan Square is conveniently located off the CTA Blue Line, smack dab in the middle between the business hub of downtown Chicago and O’Hare International. It’s got a rich mesh of Mexican-American culture and new-city vibes that come together for a really unique experience.

The area will typically boast cheaper rents than surrounding Wicker Park and Bucktown, but it’s definitely a hip area that young professionals have flocked to in recent years (Vice called it “Wicker Park's chill stoner sister,” though that’s only an quasi-accurate description depending on who you are).  It’s as flat as a pancake (a great feature for bicyclists) and easily connect to Bucktown, Wicker Park, East Village and Ukrainian Village to the south and southeast, and Avondale, West Lakeview and Lathrop across the Kennedy Expressway.  

living in chicago

Western Chicago

Let’s head a little further south toward the West Loop. This part of the city just goes to show how incredibly flexible and willing a city is to invest in an area that was once just remnants of the warehousing district it once was. Now, these brick structures have been modernized with high-class restaurants and bars (Girl on the Goat, Au Cheval, The Publican, Green Street Meats, RPM Champagne, and dozens others). The Fulton Market District, once the historic Union Stock Yards in the 19th and 20th century, now feature shops, coffee shops and restaurants and brings together River West and West Loop together nicely.

South of The Loop

And finally, let’s take a peak just south of The Loop in, you guessed it, the South Loop. After a period of stagnant construction during recession, South Loop is finally starting to be a place where those who work in the city can walk to and from. Sure, it’s not as diverse in its offerings as some of the neighborhoods out of the Printers Row, Dearborn Park or even further south in Hyde Park, it’s convenience to The Loop without actually being in the Monday-Friday hustle of the Loop is a very attractive trait for some. 

Wherever you are, most likely you won’t want to stay put. Let’s take a look at how you’ll get around. 

living in chicago

Source: yochicago.com

Transportation

From the north to the south, the west side to Lake Michigan, Chicago is one of the most accessible cities in the country. 

Sidewalks abound in this metropolitan, but taxis, CTA buses and trains (“the El”), Metra trains to suburbs east, west and south, city-bike sharing and designated bike lanes on mostly-flat streets, highways, high-speed rail and airports make Chicago a pinpoint hub for exploring the city or accessing other parts of the country with ease. And with so much to do, you’ll want the freedom of choosing how you get around.

Like any city, traffic can be an issue but don’t let that deter you from getting out and going. So let’s hop on the El first. 

You could think of the El like this: The Loop is the the heart of the city, and all trains are like veins stemming from The Loop. (If you hadn’t picked up on it yet, the Loop gets its name for its “loop” shape around main stops downtown.) Recommendation: make sure you take an extra moment to look at the Quincy stop – it’s the oldest stop in all of Chicago, evident in the old-school awning that hangs over Chicagoans waiting for their train. 

 

Photo Courtesy of CTA

And some notable things right off of train stops: Wrigley Field (Cubs) and U.S. Cellular Field (Sox), the West Loop bars and restaurants, the Logan Square movie theater, the Magnificent Mile, Chinatown, shops, restaurants and bars in Bucktown off the Damen Blue, and so much more. 

But all of this doesn’t put it into perspective. So let’s do that. 

Let’s say you decide to live on the corner of Montrose and Lincoln avenues in North Center and Lincoln Square–an area with a good mix young families and professionals and ages between, landmark parks, corner coffee shops, businesses and restaurants and no skyscrapers for miles–but you have to get to the airport to catch a flight at one of two international Chicago airports to La Guardia. Don’t have a car? No problem. Take taxi or a ride-sharing (Uber, Lyft, etc.) to O’Hare International on the west side or Midway International on the southwest side and you’ll be there in just about 40 minutes or less. 

Is public transit more your style? 

If you’re going to O’Hare, hop on the 78 Harlem bus west, which will take you straight west to the Blue Line train toward O’Hare, which will ultimately drop you off steps from your terminal. 

Buses run in every direction in the city, and you’ll wait an average of less than 10 minutes for one, depending on your timing. They’re quick, easy and there no futzing around. 

If you’re headed to Midway, get on the Montrose Brown Line, head south until you’re in The Loop, then get off at Adams. You’ll hop off, take the stairs over the tracks and hop on the next Orange Line train that ends at Midway. 

It’s a cost-effective way and often faster if you’re dealing with rush-hour jams. 

Or let’s say you’re taking your friend to see a show at The Second City in Old Town, but you want to grab a drink before at Lagunitas Brewing Company in Pilsen before. Currently, you’re at the Oak Street Beach in the Gold Coast on a Chicago Saturday, the sun shining and the air warm, the city is crowded. Let’s go. 

Indulge in a cab to the Randolph/Wabash Brown Line in the Loop and check out Gallery 37 next door if you’re interested (it’s hard to miss). Take the Pink Line to California, get off and walk eight minutes to Lagunitas. 

Grab a brew and relax in the sun (their outdoor beer garden is opening this summer). At this point you’re maybe thinking some ramen sounds good. When doesn’t it? 

High Five Ramen, the ramen that’s worth the wait, is a tiny less-than-20 seat cellar restaurant below a barbeque and coffee joint. You’ll take the Pink Line back east, hop off at Morgan, and walk less than 10 minutes to eat. 

The show starts soon at 7 p.m. and it’s 6:20 now. Get on the Pink or Green Line (they run along the same tracks), take it toward the Loop at Clark and Lake and shoot north to Wells Street at the Sedgwick stop. You’ll have a five minutes walk, but you’ll be there before the show starts, and you’ll have spent no more than 30 minutes on each train ride. 

The city is very bike-friendly and offers public bikes through Divvy, the blue bikes you’ll see people riding throughout the city. For under $100 a year, this option is great for Point A to Point B commutes, and with stations every couple of blocks you’ll find it adequately suites these trips. 

It seems nearly every business and block has a bike rack so latching up your two-wheeled ride is never an issue. 

But what will you be traveling to in the first place? Next, some things you might end up doing if you haven’t made up your mind yet. 

What You’ll Do Here 

The biggest perk about living in a big city? Chicago fits your schedule. If you work a 9-5, you’re traveling constantly, or your work hours changes week-in and out, there is always something to do. Whether you’re trying to dine and wine on a dime, or you willing to shell out a few bucks for a great time, Chicago offers a variety of options for whoever you are. 

From cultural festivals, theaters and club in all corners of Cook County to craft beer, music, book, and Comic Con festivals, 5K runs throughout the city’s streets, parks and beaches–and let’s not forget the Chicago Marathon in the fall–and the Bears, Blackhawks, Cubs, Bulls, Sox and Fire throughout the year, the city is will never short you on things to do. Some say there’s nothing better than summers in Chicago–and it’s true– but if you’re doing Chicago right there’s nothing better than calling Chicago home all days of the year.  

Say you really like venues for music – Chicago and the surrounding areas are notoriously known for them, especially during the summer.  Music is abound and alive. Acts like Paul Simon and Bob Dylan play in the north suburbs in Highland Park at Ravinia (a 40-minute Metra train from Union Station in The Loop); country music’s Windy City LakeShake is in Northerly Island in Chicago; Mamby on the Beach, an alternative/indie fest happens on Oakwood Beach, arguably the best concert on a beach in Chicago; Lollapalooza and the Taste of Chicago are in downtown’s Grant Park; Pitchfork is in Union Park; and dozens of concert at the beautiful and iconic Pritzker Pavilion in Millennium Park make this a city that’s always booming with sights and sounds.  

Pritzker Pavilion is often referred to as the "centerpiece" of Millennium Park.

living in chicago

Source: wikimedia.org

And Chicago’s sister city to the north, Milwaukee, hosts Summer Fest every year. It’s just under two hours by train, and even less by car, to get to the Brew City, a quick getaway on weekends when you want a change of scenery. 

Eating food more of the reason you’re going out? Chicago Restaurant Week is a time where restaurants throughout the city will come through with great specials, and in the last week of January, you’ll want to cope with the weather by doing this. Or Taste of Little Village, Ribfest, Taste of Chicago or Craft Beer Week in the summertime. 

Events like these on small- and medium-sized scale are happening all the time throughout every corner of the city. 

Often times, these two intersect and overlap and you’ll find that more often than not that you’ll be in the heart of an event without even knowing it. 

With festivals, events, venues, restaurants and bars, theaters and nightclubs and countless other spots and places in this great big city, you’ll find that the city is at your fingertips. Consider this your taste of Chicago, you’re brief look into your future home. There’s more to do and experience than you can fit into words, and soon, you’ll see that for yourself.