The Moveline Moving and Relocating to Chicago Guide

Part One: Introduction

Standing tall and proud on the southwestern shore of Lake Michigan, the city of Chicago is nothing if not bold. Filled with big businesses, passionate about its sports, and easily detectable in photographs by its brilliant architecture, Chicago’s known for its unapologetic prominence in everything it cares about.

Another hallmark of the Windy City, though, is its diversity. Chicago’s blend of cultures living among one another in the bustling metropolis calls to mind the energy of fellow urban meccas like New York and Boston, but with the heartiness of the Midwest as well. After all, it’s called “The City of Big Shoulders” and “The City That Works” for a reason. It boasts the tallest building in the Western Hemisphere, the country’s oldest zoo, the world’s first Ferris wheel, and one of the largest municipal libraries and collections of Impressionist and Post-Impressionist paintings in the world. In fact, when it comes to lists of things that are the “biggest,” “tallest” and “first” in the country, region, or even world, chances are, Chicago’s on it. Probably multiple times.

Living in such a hotbed of accomplishment and culture is an exciting thing in and of itself, but with so much going on at such a fast pace, it can be a little overwhelming to find oneself moving to the city and wondering where to start. So, without further ado, an insider’s guide to calling Chicago home sweet home.

Part Two: Area Guide

Chicago has anywhere from 70 to 200 distinct neighborhoods, depending on whom you ask, and each community embodies its own specific identity that’s as unique as the people who live within its borders. For new Chicago residents, here’s a rundown of what the 12 most popular areas offer:

Lincoln Park

Lincoln Park is many Chicago residents’ “first neighborhood.” If you’re new to city living, it’s a nice place to help you get your bearings. You’ll be near the Lincoln Park Zoo, which is free and open to the public year round; the Lincoln Park Conservatory, a great place to tuck into when you need a little heat in the winter; and the beautiful Lake Michigan. The bars — predominantly sports bars – each hold an allegiance to a particular college team, which is proudly displayed before you even walk in the door. The neighborhood is easily accessible by bus and the red or brown lines (see the next section, Part Three: Getting Around, for info and links to public transit).

Downtown

Generally speaking, the first instinct when moving to a new city is to live downtown if at all possible. Interestingly, though, that might be a counterproductive approach in Chicago: although the mega-affluent find solace in luxury condos at places like Trump Towers, downtown is a bit of a ghost town on weekends – during the day, at least, when coffee shops, sandwich places and the like are usually closed. Here, there are plenty of expensive high-rises with magnificent views but very little living space.

Andersonville

Andersonville is the more affordable and relaxed version of Boystown (see below). Where Boystown excels in its party atmosphere, Andersonville has a much more chill neighborhood vibe while maintaining a strong LGBT contingent. This eclectic neighborhood houses finds such as Ann Sathers, a Swedish brunch spot with enormous cinnamon rolls; The Wooly Mammoth, a store with some of the most bizarre collectibles you’ll ever see; and Simon’s, where you can enjoy homemade glögg, a strong Nordic mulled wine concoction, along with stories of Chicago’s past.

Wicker Park/Bucktown

Although they’re slowly drifting toward the mainstream, Wicker Park and Bucktown are the city’s reigning hipster neighborhoods. You’ll find live music venues, dive bars and upscale eateries alongside cool clothing stores with up-to-the-minute street wear. Expect to meet a lot of creative types, see plenty of tattoos and be treated to plenty of fashionable irony, for this is Chicago’s Williamsburg. Wicker Park and Bucktown are located along the blue line, which rides directly to O’Hare airport and can easily take you downtown, but heading to the northeast neighborhoods can be time consuming if you’re taking public transport from this area.

River North

Have lots of money and count yourself among “the beautiful people”? If so, then River North might be just right for you. This neighborhood houses Chicago’s gallery district, boasting the largest concentration of galleries in the US outside of New York. You’ll find popular nightclubs, bars and restaurants frequented by local stunners and visiting celebrities. Check out Hubbard Street for the nightlife: hot spots include The Underground, Rockit, Sub 51 and Hubbard Inn. Dress codes are enforced, so you’ll have to adhere if you want to get in.

Gold Coast/Old Town

In terms of literal translation, the Gold Coast neighborhood hits the nail on the head: this is a neighborhood for people with means, and the majority of housing options are from Chicago’s golden era. The original Playboy mansion sits in the Gold Coast, as well as, The Plymouth, a favorite hangout of the Rat Pack in their heyday. Nowadays, the area’s filled with large single-family houses, luxury condos and vintage apartments. It’s the perfect neighborhood for an afternoon stroll a series of its tree-lined streets and marvel up at its architecture.

Pilsen

This up-and-coming neighborhood boasts a booming art scene with a monthly open gallery evening. Creative types flock to Pilsen for affordable studio spaces and a growing community of like-minded artists. Housing is less expensive in Pilsen, but having a car is recommended. Public transit is available but less convenient than other neighborhoods. The best nightlife option is Simone’s, a dark and lively bar that’s well worth the trip from other neighborhoods.

Logan Square

Andersonville is to Boystown what Logan Square is to Wicker Park. This neighborhood is quickly becoming the buzz of Chicago with acclaimed restaurants, like Parson’s Chicken and Fish as well as bespoke cocktail bars and a chill, grown-up hipster vibe. Logan Square is for the Chicagoan looking for a cool and interesting scene without all the fuss. Revolution Brewery is a favorite local watering hole with house-brewed beers on tap. Logan Square is accessible by the blue line, but many residents prefer to have the option of a car or bike.

Wrigleyville

Named after Wrigley Field, the home of the Chicago Cubs, Wrigleyville is a sports-bar-lined favorite of Chicago’s die-hard sports fans. You’ll find them everywhere, enjoying pitchers of cheap beer and late night pizza decked out in their teams’ gear. Wrigleyville is located along the red line and easily accessible by bus.

Boystown

As hinted in its name, Boystown is the epicenter of Chicago’s gay community. It hosts quirky collectibles stores like Gay Mart and drag queen martini bars like The Kit Kat Club alongside old-school video game bars and popular restaurants. Hydrate, Roscoes and Sidetracks, all located near each other on Halsted Ave, are favored hangouts for the style-conscious, and Whole Foods, Jewel and Treasure Island are all within walking distance for a quick grocery run. Several buses go directly downtown, while the red and brown lines offer an even quicker, albeit more crowded, commute.

Ukrainian Village

This is Chicago’s next big neighborhood. Located just south of Wicker Park, Ukrainian Village has all the perks and excitement of the hipster haven, but with relatively quieter streets. Community gems include Trattoria Ultimo, a locally-owned Italian restaurant with fresh, delicious dishes, and the neighboring Atomix for coffee. Ukrainian Village is a bit distant from L stations, but getting downtown isn’t too difficult by traveling east on either the Grand or Chicago Avenue buses.

Part Three: Getting Around

Bus and Trains

Owning a car is mostly unnecessary for navigating your life in Chicago. The CTA, which stands for Chicago Transit Authority, is a thorough and convenient system of buses and elevated trains, known as the “L.” Trains are $2.25 per ride and buses are $2.00. You can pay in cash when boarding, but most residents choose to use the Ventra card for convenience. Simply tap the card against the circle on the turnstile at the entrance to the trains or by the driver on the bus. This will automatically take the fare from your account.

Biking

Many residents in Chicago opt to bike their way around town since it’s faster than walking and offers more flexibility than taking the CTA. Bike lanes are outlined on most streets, but it is still very important to stay alert when biking in congested urban areas. Bikes are allowed on both trains and buses, if you would like to blend your journey. Biking has become so popular in Chicago that Divvy, a new bike-sharing company, has launched rental stations in plentiful locations throughout the city. Buy a membership or pay per ride.

Cabs

Taxis are easy to hail in most neighborhoods and are legally required to accept debit and credit cards. Smart phone apps like Hailo and Uber have thoroughly changed the taxi experience. Download either app to your phone and arrange for a cab to pick you up with the touch of a screen. Apps like these are especially helpful during poor weather and in less-trafficked neighborhoods. You’ll never have to stand out in the rain waiting for a cab again!

Rideshare

Maybe you want the convenience of a car, but taking taxis everywhere just seems too extravagant. New smart phone apps like Lyft, SideCar and UberX hook you up with citizen drivers who pick you up and drive you to your destination for a fraction of the cost. The only caveat: there are fewer rideshare drivers on the road than cabs, so availability can be limited.

Grocery Delivery

Grocery stores are abundant and easily accessible in most Chicago neighborhoods. If you don’t want the bicep workout of dragging your bags home, Peapod is a grocery delivery service that allows you to order online and have items dropped off at your address. You’ll pay a higher premium for food, but depending on your location and lifestyle, the time saved could be worth it.

Part Four: Whistle While You Work

The Windy City is home to the Federal Reserve Bank, Chicago Board of Trade, and Chicago Mercantile Exchange; it’s second only to New York in the publishing industry; and it’s known as the “candy capital” of the United States. The diversity of its business sectors is impressive: manufacturing, printing/publishing, finance/insurance, and food processing are the primary pillars of the city’s economy.

The town’s business dealings aren’t exactly dwindling in the current economy, according to most experts. Per World Business Chicago, “Total trade reached $188 billion in 2012 (up from $154 billion in 2008). Chicago is top-ranked for economic potential among major cities across the world, and in 2012, World Business Chicago identified more than 600 new & expanding facilities announced, under development or completed in the metro area, representing a total of 35 million square feet and $10.5 billion in economic development activity. In 2013, Inc. Magazine included 252 companies from the Chicago region in its annual list of the 5,000 fastest-growing companies in the U.S., placing Chicago 4th among metro regions for number companies ranked.” So needless to say, comparatively speaking, jobs in all sorts of pursuits are in strong supply.

For those who work remotely or are sole proprietors or entrepreneurs, there’s no shortage of coworking spaces, either. NextSpace Coop, 1871, Enerspace, Catapult, ChicagoGrid, and Onward all offer hospitable working spaces for those in need of a suitable office without the confines and constrictions of a traditional workplace.

As in any other city, networking can play an important role in finding the perfect job and advancing one’s career, as can research and preparation. For detailed information on the local employment outlook, visit the Chicago Tribune‘s Jobs section, and of course, the usual suspects are always on hand to help — LinkedIn, GlassDoor and Indeed are three tried-and-true resources for employment seekers as well, not to mention staffing agencies.

Part Five: Eat, Drink, Shop, Play

Given its propensity to top lists the world over when it comes to the biggest and best of everything, it’s no surprise that Chicago offers some of the most staggeringly good food, drink and diversion in the U.S. Here’s a sampling of some spots that aren’t to be missed:

Best Coffee

Intelligentsia (Lincoln Park, The Loop and Logan Square) or Wormhole (Wicker Park) – Intelligentsia coffee is sold at many restaurants throughout the city, but you’ll want to make a stop at one of their three coffee bars for the full experience. Intelligentsia beans are roasted to notable perfection for a smooth and unmistakably characteristic flavor. Their baristas are highly trained and frequently rank highly at worldwide barista championships. Alternatively, notable for its Delorean, its vintage Nintendo gaming station and its 80s memorabilia, Wormhole also serves a delicious cup of coffee. Expect a wait as the team likes to take its time with each customer.

Best Burger

Lockdown (Ukrainian Village), DMK (Lakeview) or Kuma’s Corner (Avondale) – The good news is, there are plenty of choices; the bad news is, it’s almost impossible to decide. Lockdown, for one, is a prison-themed joint (yes, prison) with big burgers and inventive toppings. DMK is located across from The Vic, a popular live music venue, while Kuma’s Corner is a rock-themed restaurant with new burger every month dedicated to a different band.

Best Tacos

Big Star (Wicker Park) – Although it’s a tight competition, Big Star is the reigning favorite. Items are created by Michelin-starred Chef Paul Kahan and change with the seasons. The spot is very popular, cash-only and doesn’t accept reservations, so expect a line. (Pro tip: watch out for the margarita pitchers. They sneak up on you.)

Best Donuts

Glazed and Infused (West Loop, Wicker Park and Lakeview) – These donuts just might change your life view. A seasonally-revolving menu capitalizes on the best ingredients and flavors available at any given time of year. Expect to have your mind blown.

Best Brunch

Lula Café (Logan Square) – Super delicious and locally sourced, this unassuming little spot is the perfect place to roll into for scrumptious, fresh breakfast and lunch options after sleeping in on a Sunday.

Best Cocktail

Violet Hour (Wicker Park) or The Aviary (West Loop) – The Violet Hour is a secret bar hidden behind a wall of commissioned street art. There’s no sign, no windows. The only way to locate the bar is to look for a lone light bulb on a building across the street from Big Star — the light bulb is on when the bar is open. Once inside, you’ll be directed to small tables with high-backed chairs reminiscent of a Mad Hatter tea party. Cocktails here are so precise that the mixologists use tiny droppers to get the flavor just right. As for The Aviary, it’s located on Restaurant Row in the West Loop. Book a table far in advance as reservations go quickly. Each cocktail at The Aviary is an interactive experience using slingshots, beakers, aromatics and other tableside techniques.

Best Late Night

The Owl (Logan Square) – This 5 am bar is a good place to find yourself on the weekends after the rest of the bars have closed. Expect a line to get in after 2 am, but street food vendors are on hand to keep you satisfied during your wait. Expect good music and the crowd is a little less rowdy than other 5 am bars.

Best Celebrity Spotting

Sunda (River North) – Owned by the folks behind Rockit, Ay Chiwowa and The Underground, Sunda is an Asian-fusion restaurant with a loyal celebrity following. Feed on inventive sushi and tapas-style dishes, while taking in the sites of a glam city-dwelling crowd. Expect to make reservations in advance as the tables fill up quickly.

Best Chicago Classics

Chicago has three signature staples when it comes to food: the hot beef sandwich, the deep dish pizza and the Chicago-style hot dog. Options are abundant for all, but your best bet for a hot beef sandwich is Al’s Beef (with multiple locations throughout the city), one of the best deep dish pizzas can be found at Pequod’s (at Webster and Clybourn, just west of Lincoln Park) and you can’t beat Hot Doug’s hot dogs (at Roscoe and North California Ave, near Brands Park). If this trio of eateries doesn’t give you a true taste of Chicago, nothing will.

Best Shopping

Everybody needs something sometime. Whether it’s a new pair of winter boots or just an excuse for a little retail therapy, the Windy City is no slouch when it comes to shopping options. Here, a quick rundown of some places to check out:

Belmont Army (855 W Belmont Ave) for trendy clothes within a moderate price range. It carries a mix of national name brands and local designers.

Akira (122 S State St) is a local favorite, carrying both men’s and women’s clothing. It’s locally owned and carries both low- and high-end brands.

Sir & Madame (938 N Damen Ave) is another trendy, locally owned store for men’s and women’s clothing.

St. Alfred (1531 N Milwaukee Ave) is the ideal place for “sneakerheads” — lots of young local businessmen in particular are starting to identify with that culture, and St. Alfred’s is just the place to indulge them.

LDRS (672 N Wells St) is a men’s streetwear shop with lots of tees and sweatshirts by local designers.

Oak Street (in the Gold Coast neighborhood) is essentially Chicago’s version of Bond Street, with Barneys, Prada, Jimmy Choo and fellow couturiers selling the some of most expensive goods in town.

900 Shops (900 N Michigan Ave) anchors the north end of Michigan Ave and encompasses six levels of shopping, from Adidas and Bloomingdale’s to Sur La Table and UGG.

Block Thirty Seven (108 N State) is a lesser-traveled mall-esque atmosphere popular with the ladies since it houses Zara, Sephora and Anthropologie all under one roof.

Pro tip: While Michigan Ave has plenty of popular chain stores (think GAP, JCrew), it’s also overrun with tourist foot traffic. Since it’s typically crowded and hard to get in and out of, locals generally avoid the area for shopping. The only exception in the area might be Water Tower Place (835 N Michigan Ave), which locals love for its broad but closely concentrated range of stores.

Best Places to Meet People

If you move to Chicago in the summer, you’re in luck: the city’s big on street fests during the warmer months. Several take place simultaneously almost every weekend and each neighborhood has its own. Festivals are a great way to explore Chicago, and you’ll meet all kinds of people just looking to have a good time. Keep an eye on the city’s official website for dates and details.

All year round, though, late night parties at museums are another great way to mingle without trying too hard. Adler Planetarium, MCA (the Museum of Contemporary Art) and Art Institute all have late night mixer/parties on a monthly basis. Tickets can get a bit expensive (typically around $20), but it’s a great place to meet young professionals. A quick pointer: the MCA mixer can be a bit of a singles’ scene (some might even say “meat market”), while the others are more laid-back, socially speaking.

If you’re the career-minded sort who wants to make connections within your industry — or just to meet people who get where you’re coming from — the city plays host to a number of professional and community-based associations. Whether you’re a banker, a teacher or a restaurateur or you work in tech, hospitality or accounting, there’s a group for you to join and all sorts of connections for you to make. Chicago is a highly-networked city; take advantage of it if you’re new.

Meetup‘s got something for everyone in Chicago, whether it’s a writers’ group or a bunch of fellow raw food enthusiasts you’re looking for. Sports fans, dog lovers, political junkies and athletes can all get their fix with Meetup groups tailored just for them. No joke: there are more hundreds — hundreds — of groups within the city. So it’s statistically probable that your new crew is out there somewhere, just waiting for you to hang out with them.

Part Six: Weekend Ideas

Particularly if you’re not overly familiar with Chicago upon your arrival, there’s a laundry list of tourist attractions to go ahead and check out. Unlike a lot of counterparts in other cities, most of the “touristy” sights here are genuinely worth experiencing, no matter where you live.

Perhaps most famous are Cloud Gate (more commonly referred to as “the bean”) and two tall towers: the John Hancock Observatory, which offers the best view of the city from its observation deck (which also serves coffee and alcohol) and the Willis Tower, formerly known as the Sears Tower, which offers “The Ledge,” a series of clear boxes jutting out of the building, where visitors can test their nerves by stepping out and looking down from 103 stories above the earth. Clearly, those with a fear of heights might want to skip the towers, but for those don’t mind an occasional spike in their heart rate, both offer a sense of scale and give an idea of the city’s layout from a bird’s eye view. Not a bad way to start a Chicago adventure, really. 

Millennium Park offers great concerts in the summer, ice skating in the winter and seasonal exhibits throughout the year, while the Lincoln Park Zoo is free and open year-round. There’s no shortage of popular museums to visit for a little cultural enrichment, from the Art Institute (housing a huge collection of Impressionist paintings) and the Museum of Science & History to the Field Museum (featuring everything “from dinosaurs to DNA”) and Shedd Aquarium. While all are perennially high on visitors’ lists of things to do, they’re worth checking out by locals new and old as well.

For those who prefer the road less traveled — or the waterways, for that matter — the Chicago Architecture Foundation offers brilliant architectural boat tours along the Chicago River, giving a unique glimpse by boat at the city’s staggering architecture along with historic context given by a trained docent.

The Chicago Cultural Center houses a series of galleries filled with celebrations of the arts, education, Chicago and the world around it. The building itself is nothing to sneeze at, either; the historic landmark is a feat of stained glass and classic hallmarks of local architecture. It hosts lectures, concerts and an array of rotating events throughout the year, all with a strong cultural angle, true to its mission.

The view of the city from the Adler Planetarium‘s steps is arguably the best and most iconic, and pictures don’t do it justice; it has to be seen in person for the full effect. Luckily, the center’s programming is fascinating as well: its immersive sky shows are a great way to pass the time and learn something about the universe from the comfort of state-of-the-art theaters retrofitted into the Western Hemisphere’s oldest planetarium.

Last but not least, the Palmer House Hotel holds a little-known secret: it’s the birthplace of the chocolate treat known as the brownie. Proud of its heritage, the hotel bar offers brownies in addition to its usual libations. A gooey bite of goodness seems a fitting way to bring a day’s exploration of your new town to a very sweet conclusion.

And for an adventurous agenda that’s perfectly tailored to suit what you’re into, check out hyperlocal discount sites and apps like Groupon for extracurricular ideas (not to mention super-sweet deals!) on everything from restaurants, gyms and spas to groceries, getaways and once-in-a-lifetime experiences.

Conclusion + Resources

Whether your move to Chicago is for a job, a loved one or just a change of pace, there’s something in it for you. It might be a business opportunity, a new set of friends or simply the general rush of excitement that comes from living in such a busy and enriching place — in any event, home is what you make of it. And if you need help getting yourself moved, give the team at Moveline a try. We take the headache out of the moving process so you can focus on more important things, like getting acclimated to your amazing new city.

Helpful Links:

Get A Moveline Quote, Choose Chicago, Chicago Chamber of Commerce, Chicago Tribune, Chicago Sun-Times, ChicagoNow, RedEye, MetroMix, LinkedIn, GlassDoor, Indeed, Trulia, Zillow, Apartments.com, WalkScore, Groupon