Chicago – City Guide


ChicagoChicago City Guide For First Time Renters
Updated August 2015

By Alissa Green

What people don’t tell you about Chicago is that it’s really the city of The Neighborhood. That’s why we put together this city guide with all the neighborhood info you need to explore your new city.

With 77 official city community centers, many Chicagoans feel great love for their resident ‘hood, with North Side/South Side pride running especially rampant during the summer baseball season.

At first glance, choosing the right place to set up shop might sound difficult, overwhelming even. So, take a deep breath and don’t worry—because from the artsy houses of Wicker Park to the frat houses of Wrigleyville, there really is a place for everyone. Plus, after reading this, you’ll be so good at separating what’s hot from the hype that people might even mistake you for a local.

Some General Chicago City Guide Notes:

  • Keep in mind that in terms of rent that the further you stray from the Loop, the cheaper your life will be. (Supply and demand at its finest.)
  • If you live in a ‘changing’ neighborhood, the closer you are to public transportation, the greater likelihood the surrounding blocks will be gentrified.
  • As of 2015, Chicago is the ninth-most expensive city in the country, with the median one-bedroom pricing out at $1696. But – and this is important – it really will vary by neighborhood. Good deals can definitely still be found if you are fine living in quieter (but still safe) neighborhoods.
  • Please keep in mind that there are certain precautionary measures that need to be taken in urban areas. Keep your eyes open when you find that perfect apartment and be sure to walk around the surrounding neighborhood at least once late at night before you sign the lease. What may seem safe during the day won’t necessarily feel safe after sundown.

Popular first time renter neighborhoods include: Andersonville, Lincoln Square, Wrigleyville, Lakeview, Lincoln Park, Gold Coast/River North, Ukrainian Village, Wicker Park/Bucktown, Logan Square.

Neighborhoods good for year two: Ravenswood, Edgewater, Roscoe Village, North Center, West Town, West Loop, Noble Square. Humboldt Park and Rogers Park are also good choices especially if you are looking for places on the cheap.

Need Car? No, especially with the rise of Divvy, car sharing services and Uber. However, if commuting to work in the suburbs, it can be vital.

Check Apartment Classifieds:

The Apartment People and The Apartment Finders (fairly interchangeable but read more reviews on Yelp) can often show you 5 places in a single morning and best of all — they’re paid for by the landlord, not you! That said, you can probably find a better place on your own with a little more leg work.

Classifieds can also be helpful. We recommend:

Other ideas? Take a quick walk around your neighborhood of choice. There are often ‘For Rent’ signs posted.

The Chicago Commute:

While it’s probably not good to pick a neighborhood based solely on its proximity to work, in Chicago’s case, it would be prudent to at least consider it as a factor. The El, short for elevated train, is Chicago’s aboveground subway, and while it gets the job done, it can take upwards of an hour from certain parts of the city, especially the far north side. Also, the train stops are much farther apart than, say, New York. As such, if you plan to work in the Loop, the main business district, it would be wise to live near an El stop, Express Bus Line or Metra Train line as street parking is nil.

Additionally, if your job is, say, off of the eastern Red Line, living near a western Blue Line can be a time drain if your job isn’t in the loop. The Chicago Transit Authority is a good resource for both El/Bus schedules and stations. You can find Metra info here: Also, with the advent of apps like Bus Boy, the buses in Chicago are much more palatable. This Chicago transit app list from Grid Chicago is definitely a must-read for new and old Chicago renters alike.

Likewise, if you plan on driving, do keep in mind that Chicago is a relatively spread-out city. There are a few highway options, but during rush hour you might as well grab a picnic basket and lay out a red-checkered tablecloth on your hood—that is seriously how fast you will be traveling.

Furthermore, many jobs are to be found in the surrounding Chicago suburbs, which geographically aren’t far. However, if you are going to be working in northeast Deerfield, the 25 mile journey from southwest Ukrainian village could very well take you over an hour. I have the joy of working in Rosemont (in the backyard of O’Hare) and it takes me a solid 50 minutes there and 60+ minutes coming home most nights.

Chicago City Guide: Neighborhoods

Now that you can narrow down your perfect Chicago neighborhoods by commuting time, it’s time to identify what neighborhood characteristics you want versus what neighborhood characteristics you need. Need affordable housing? A gay-friendly atmosphere? A 12-block strip perfect for a Saturday morning eat-n-stroll? Andersonville might be for you.

Value your proximity to the Lake and to the Loop? Posh bars and restaurants? Lincoln Park or the Gold Coast might be your ticket. Living amongst trendy singletons a priority? Logan Square or Wicker Park, both located on the West side sounds about right.

Honestly, any of these 10 neighborhoods would be great to have as a home base to explore Chicago. But if for some reason none sound appealing, just remember: you have a whopping 68 others to choose from.

****If you want an apartment building with a doorman, indoor workout space, etc. you will be at the higher end of all figures, though the absence of these amenities does not guarantee a lower price.

Chicago Downtown:

South Loop/Gold Coast/River North

Living in the center of any metropolitan area is going to be pricy and usually with good reason: you’re in the center. Of everything. Chicago’s downtown landscape is slightly different. While the economical epicenter of Chicago is the Loop, after 7 p.m. on weekdays and all weekend, the Downtown business district begins to resemble a sky-scraper filled ghost town, though it’s definitely been improving over time. Mostly though, those in the loop on the weekend are tourists though, as well as older, wealthy Chicagoans who have bought a condo in the sky.

That said, the City of Chicago continues to make extraordinary efforts to rejuvenate the Loop, often bringing in weekend festivals and making continual residential renovations. The South Loop has successfully transitioned to become a vibrant community; the leafy, residential pockets are perfect for families, though the Chicago School System leaves much to be desired. If you’re thinking – wait – I am SO not anywhere near having a family, why would I live there? Think: walk to work and walk to the beach. There are also multiple big-box retailers (with almost a suburban feel) and a nice movie theater in the South Loop, nowadays.

  • Studio: $1787-1823
  • 1 Bdrm: $1800+

Meanwhile, the Gold Coast, long known for its upscale inhabitants and du jour nightlife, continues to glow amidst its high rises placed strategically along Lake Shore Drive facing Lake Michigan. While there are a select few Chicagoans who would desire to be ‘seen’ at a certain restaurant, you will find all the beautiful people that do in the Gold Coast near the trendy intersection of Rush and Division. The expensive restaurants and clubs that line the intersection are also where you may have your local celebrity sightings.

  • Studio: $1323-1883
  • 1 Bdrm: Upwards of $2000

**If you want an apartment building with a doorman, indoor workout space, etc you will be at the higher end of all figures, though the absence of these amenities does not guarantee a lower price.

River North, meanwhile, plays host to a plethora of theme restaurants and bars, the tourists who frequent them, and a gajillion art galleries. (FYI: the most anywhere in the country outside of Manhattan). Steps away from the Magnificent Mile, if you live here you’ll likely be renting a condo or a loft. Prices are comparable to the Gold Coast.

Best Gold Coast, River North and South Loop Neighborhood Features:

  • Rolling out of bed and be at work pronto!
  • The closeness to Chicago’s biggest theaters.
  • A hop, skip and a jump to Chicago’s best museums, including the world renowned Art Institute.
  • A nightlife shaken, stirred, and to die for.

City Near North:

Lincoln Park

Amongst the most popular neighborhoods for 20-somethings, what Lincoln Park lacks in diversity, it makes up for in hot bars, restaurants, and general convenience. Home to DePaul University as well as many a historic brownstones, Lincoln Park is the first, and often last, stop for many folks who think they know what they want in Chicago. Living in Lincoln Park guarantees closeness to the lake, Starbucks, and that sexy girl at your advertising firm earning in the upper 5 digits. Realize you will be paying for the ‘luxury’ of saying you “live in Lincoln Park.”

Lincoln Park Best Neighborhood Features:

  • Lincoln Park Zoo—housing animals from antelope to zebra.
  • Host to the famous Second City, i.O and Steppenwolf theaters.
  • High energy, exclusive bars and clubs similar to those at Rush and Division; these are not the places for a quiet beer with friends.
  • College dive bars near DePaul University.
  • Studio: $875-1295
  • 1 Bdrm: $1750+


One of Chicago’s largest neighborhoods, Lakeview continues the geographically eastern trend—though moves further north. Bordering Lincoln Park to the south and Uptown to the north, Lakeview is a less expensive version of Lincoln Park, particularly in Lakeview West. Be warned though: Parking is nigh impossible to find, so make sure to buy a parking spot if you want to live near the lake and drive, though there are tons of El stops. Boystown and North Halsted are other communities within Lakeview.

Lakeview Best Neighborhood Features:

  • Gay Pride Parade every summer
  • Belmont has Red line, Brown Line and Purple line trains
  • Recreation Drive, which can be reached before the Belmont Exit on LSD has tennis courts, bike and running paths, and other water sports activities.
  • Perfect for those fresh out of college, especially if you love the Big 10.
  • Studio: $865-1115
  • 1 Brdm: $1400

City North:


While maps will indicate that Wrigleyville is, in fact, a subset of Lakeview, do not be fooled: It is a thumping frat party unto itself. Home of the Chicago Cubbies and sports bars galore, be prepared to encounter plenty of bros and drunken early 20-somethings (especially at night but really any time there’s a Cubs game). Hopefully, they’ll leave your apartment building unharmed, but empty beer bottles may be a thing.

Wrigleyville Best Neighborhood Features:

  • While indie concert hall, The Metro, might gag at being associated with Wrigleyville, it can’t deny its address. Also close by are concert venues Schubas and The Vic.
  • Cheap drink specials most nights of the week along the Clark St. Strip.
  • Easy access to Southport Corridor which features cute boutiques and the vintage Music Box Theater (replete with organist, Art Deco architecture and red velvet curtain).
  • Studio: $775-1015
  • 1 Bdrm: $1980- $2368


Originally THE Swedish neighborhood of Chicago, Andersonville has expanded in recent years to include many a liberal, artsy, and open-minded Chicagoan. The (ever-expanding) Clark street strip is the main drag of Andersonville and there aren’t oodles of cute cafes and brunch spots as well as a neat bars. Another fast Andersonville fact is that in recent years, it has become Chicago’s “Girlstown”, as counterpart to Lakeview’s “Boystown.”

Andersonville Best Neighborhood Features:

  • Home of the famous and totally tasty Swedish Bakery.
  • Women and Children’s First independent bookstore has frequent author readings as well multiple free book clubs open to all.
  • Lots of great and diverse restaurants at great prices (Turkish, Thai, Italian, Mexican, Middle Eastern, Tapas, Swedish to name a few…).
  • Park your car with ease—then walk/bike to the lake!
  • 1 Bdrm: $1350 (but as low as $800 and as high as $1895)
  • 2 Bdrm: $1400-$1950

Lincoln Square

If you’re looking for that old world, European feel, look no further than Lincoln Square, especially if you dig everything German. While some may complain that Lincoln Square has served up more strollers than sidecars in recent years, few would deny its appeal as a first neighborhood, especially for those coming from less urban areas. At its core, Lincoln Square resembles a small town nestled within a bustling city with the benefits of both, such as inexpensive housing with a wide array of urban delights.

Lincoln Square Best Neighborhood Features:

  • Gene’s Sausage Shop whips up traditional German goodies like no other place in town. The annual German Fest in late summer is also quite the wunderbar affair.
  • If you’re a book fiend, one of Chicago’s largest public libraries, Sulzer, will be right down the block.
  • Brown Line access.
  • From its local apothecary to its old school bowling alley, Lincoln Square can’t help that it’s totally charming.
  • Summer concerts in the square
  • 1 Bdrm: $1200 – $1500
  • 2 Bdrm: $2000 – $2565

Chicago West

If you want diverse and progressive city living, find an address within Logan Square. Home to rich Latino and Eastern European communities as well as an increasing number of college-educated hipsters, Logan Square is one of the hottest neighborhoods in the city. Think the Bushwick of Chicago, for those familiar with New York. Certainly more residential than Wicker Park/Bucktown, Logan Square is great for those who value tree lined boulevards with a side of the eclectic.

Near Chicago West:

Ukrainian Village

The Ukrainian Village has changed tremendously in the past twenty years, especially in areas close to public transportation. What used to be slums have transformed into independent coffee shops, art galleries, and… Orthodox Churches? Actually, those have always been there.  Regardless, for those wanting an urban + neighborhood experience, the Ukie village might be your best bet. However, while Ukrainian Village used to be a cheaper cousin to Wicker Park/Bucktown, it’s not much of a secret anymore. Be prepared to pay

Ukrainian Village Best Neighborhood Features:

  • A host of distinctive bars—with a special shout out to the Rainbo Club and the Empty Bottle, which also doubles as a concert venue.
  • Proximity to Hipster bustle without being in the actual fray.
  • Great selection of ethnic grocery stores.
  • Close to Downtown.
  • 2 Bdrm: $1650 – $1850
  • 4+ Bdrm: $3850 – $4500

Wicker Park and Bucktown

Wicker Park and Bucktown could be considered the Ukrainian Village’s twin—if you discounted all the gentrification. While different communities, they’ve begun to greatly resemble each other, with Wicker Park clocking in at an upper case HIPSTER and Bucktown veering more towards upper case YUPPIE, though its often difficult to tell them apart. In both neighborhoods you’ll find a foodie, artsy paradise that rivals Lincoln Park for the title of Chicago hip. Walking down the streets, you’ll be passed by fashionable denizens flittering about in leggings, fringe or whatever fashion is currently hitting NYC. There are also a multitude of boutiques and art galleries just waiting to be frequented.

Wicker Park and Bucktown Best Neighborhood Features:

  • Hipsters and Artists. Lots of ’em. Watch the F*%^ out. Or, joint right on in.
  • A host of eclectic art and neighborhood festivals and a supportive artist community…at least when it’s not making them starve by raising their rents?
  • A kickin’ live music scene anchored by the Double Door and Subterranean.
  • Easy access to the new 606 bike path.
  • 1 Bdrm: $1200-$1500
  • 2 Bdrm: $2000 – $2565

Chicago North West:

Logan Square

If you want diverse and progressive city living, find an address within Logan Square. Home to rich Latino and Eastern European communities as well as an increasing number of college-educated hipsters, Logan Square is one of the hottest neighborhoods in the city. Think the Bushwick of Chicago, for those familiar with New York. Certainly more residential than Wicker Park/Bucktown, Logan Square is great for those who value tree lined boulevards with a side of the eclectic.

Logan Square Best Neighborhood Features:

  • 10 years ago, Logan square was just developing into a vibrant neighborhood. It’s now arrived – and big time.
  • Proximity to nearby alternative music shows and happenings, especially the Logan Movie Theater.
  • Whisky, Gin, and other specialty cocktail bars, anyone? What about organic restaurant fare at the fabulous Lula’s Café the next morning?
  • Insanely awesome Sunday morning farmer’s market.
  • Wide variety of ethnic grocery stores.
  • Studio: N/A
  • 1 Bdrm: $675-1100

Also check out this infographic that shows Chicago’s rent levels by subway line.

What did you think of our Chicago city guide? Let us know if you have any extra tips!


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Author My First Apartment

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I've lived in apartments in 6 cities (including 2 foreign countries). Does that make me an expert? As of now, my ceiling isn't leaking and I don't have rodents (knock on wood) -- so I'm going to say yes . . . but ask me again tomorrow:) These days, I'm enjoying life Chicago style, but my years in Brooklyn are never far from my mind. P.S. By day I work at, but these opinions are totally, 100% my own.

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