Bucktown
Though some proud preservationists will give you a line about the goats that used to graze in the pastures around the turn of the twentieth century (the male of that animal being called a buck), the local legend that you used to be able to get a hooker for a dollar in the area's numerous brothels is a much more fun story to believe. But no matter how Bucktown got its name, there's no denying that it's one of Chicago's hottest neighborhoods, loaded with interesting restaurants, shopping, nightlife and other all-around trendiness. Slightly more upscale than its artist-infested neighbor to the south, Wicker Park, and slightly more hip than its partner-in-crème across the Kennedy, Lincoln Park, Bucktown is largely comprised of old cottages and early twentieth-century two- and three-flats (many rehabs) and is increasingly becoming peppered with loft condos and brooding multi-unit buildings. Though not entirely without its gritty charms (read: there are still hookers-a-plenty by night), the general trendy bustle and the proximity to the Damen and Western Blue Line stops make the neighborhood an appealing place for the young, urban, professional set to lay its head. But all this comes at a price, as BT is one of the priciest places to live west of the expressway, though a sweet deal isn't unheard of—yet.

Edgewater
Frequently paired with its northern neighbor, Rogers Park, Edgewater is actually getting a faster facelift as the rehabbers take hold of the neighborhood's long stretch of Lakefront high rises. But never fear, you can still get a larger, cheaper apartment up north than you can just about anywhere elsewhere in the city. West from the Lake the housing stock becomes everything from beautiful courtyard buildings to converted hotels, and though you might have to live with older fixtures in a place that hasn't yet been revamped, you're liable to reap the benefit in cheaper prices. The area itself bustles along main corridors like Sheridan and closer to the Lake, and though it's not exactly a shopping mecca, there are a nice selection of local pubs and restaurants along main corridors like Broadway, and helpful things like grocery stores dotted throughout. More selection can always been found by heading down into nearby Andersonville or north into Rogers Park. Parking here isn't horrible yet, though it can get tricky around the larger apartment buildings—but you can always leave your car at home and hop the Red Line.

Humboldt Park
A neighborhood anchored by its sprawling namesake park, Humboldt Park is one of the areas you can go to in the city and see gentrification at work, for better or worse. A proudly Puerto Rican neighborhood (large flag fixtures arch over some of the main arteries) that has seen an influx of college students, artists and other folk looking for cheap rents moving in, there are little pockets of Humboldt Park that could be described as hostile to any newcomers unwittingly (or not) bringing the gentrifying wave of white to the area. Despite that factor, which isn't present everywhere and most likely on its way out, Humboldt Park offers scores of apartments—some old and charming, some modern and streamlined, with dishwashers, air conditioning and all the other goodies you could want. Nightlife is a burgeoning development here—a few fine establishments can be spotted on California, but there's not much else. With public transportation, you're mainly limited to buses.

Hyde Park
In real-estate parlance, Hyde Park is not a "destination neighborhood," meaning people don't go there unless they live there. But those who do live there—University of Chicago professors and students, middle-class African Americans, and well-meaning white liberals—love it. Hyde Park's main shopping area, 53rd Street, is pleasantly run-down, with useful stores, Afrocentric craft shops and galleries, and lots of cheap restaurants—Thai, Japanese, Italian, Indian, and let's not forget that South Side institution, Harold's Fried Chicken. If you're not a student, nightlife in Hyde Park is non-existent, because the university rules this nearly dry neighborhood with an iron fist. For years, Hyde Park had four bars. In the last year, with the closure of Ciral's House of Tiki, that number has been reduced to a pathetic three—one excellent (the Woodlawn Tap, known by old regulars as Jimmy's), one seedy (the Cove) and one seriously sketchy (the Falcon). Hyde Park is a strictly make-your-own fun neighborhood (preferably by reading Aristotle or Heidegger). Nonetheless, it has an enormous amount to offer—the Gothic architecture of the university, Promontory Point (the most attractive section of Chicago's Lakefront), several world-class museums (the Oriental Institute, the Museum of Science and Industry), Doc Films (the oldest independent film society in the nation, which shows a different film every night during the school year), and in the winter, open-air skating on Midway Plaisance.

Lakeview
One of Chicago's largest neighborhoods in terms of geographic size and white-culture diversity, Lakeview offers something for everyone—at a price. Encompassing Wrigleyville, Boystown and running much further west, Lakeview is a hive of activity, services, restaurants, bars and public transportation, which understandably makes it a very desirable place to live. It comes at a cost though; like the rest of the city, the closer you are to the train, the more expensive the apartment. However, apartment prices aren't that much higher than the rest of the city—the issue lies with amenities. Parking spaces, air conditioning, in-unit washer and dryer and wide spaces are rare. But unlike other like-priced areas, the uncountable number of restaurants (from fast food to high-end) and nightlife makes up for cramped living quarters. The perfect place to live if: You are new to—and slightly intimidated by—the city and are unfamiliar with the intricacies of the neighborhoods.

Lincoln Park
Although when you think of economically disparate neighborhoods Lincoln Park doesn't exactly come to mind, it's worth noting that this North Side neighborhood has two very distinct price ranges: expensive, and really, really expensive. From west to east, Lincoln Park becomes increasingly more posh and, with that, pricey. But you get what you pay for. While the west side of Lincoln Park offers smaller places, the nightlife is virtually unparalleled, from its local collection of taverns and restaurants to its proximity to the Steppenwolf theater district and downtown. To the east, beautiful, single-family million-dollar houses become more predominant; as a general rule of thumb, the closer you get to Lincoln Park Zoo, the more extravagant the homes. If you were the type who hated fraternity and sorority kids, Lincoln Park is not for you—all those kids got jobs, and now they all seem to live here. There are loads of baby-carriage-pushing moms and dads as well, contributing to a more family-oriented atmosphere during the day. At night, however, especially along Halsted and Armitage, noise and more noise is the order as the area explodes with activity.

Lincoln Square
Though sometimes confused with its eastern neighbor, Ravenswood, Lincoln Square (running roughly from Irving Park to Foster and encompassing the main arteries of Damen and Western avenues) has its own distinctive flavor. It's better to say that Ravenswood and Lincoln Square complement each other—the housing stock is similar, nicely vintage with some larger apartment buildings and access to the floors for rent in two- and three-flat buildings. The uniqueness of Lincoln Square rests in a wonderful German background (many residents still speak in native tongue), which has been flavored by new Eastern European residents and even an influx of Latino and Korean businesses. Numerous cafés, from the amazing Café Selmarie to the wonders of Café Lutz, make this an area to tarry over coffee and pastry and the Chicago Brauhaus (along Lincoln) remains one of the jewels of local German fare restaurants. The amazing Sulzer Regional Library, just south of Lincoln Square, along with the charming set of pedestrian-oriented shops along Lincoln between Lawrence and Leland, ensure you'll never have to go downtown, unless you want to. Parking is still fairly easy and the Brown Line is easily accessible by heading into Ravenswood.

Logan Square
It's all about the boulevards. Logan Square's top draw has to be its aesthetic, with the tree-lined streets, patch-lawns and grassy medians marrying themselves perfectly with the neighborhood's classic two-flat graystones. In fact, more than half of the housing stock is comprised of these dual-family buildings, said to incorporate a variety of the favored architectural features of early immigrants rather than following a school of design to the letter. It's this unique character that seems to form a bond among its residents. A hotbed of multiculturalism, the area is a mosaic of race, age and creed that seems to function quietly and friendly rather than turn into a experiment in gentrification like its neighbors to the southeast. But its placid semi-seclusion has an end on weekends, when Milwaukee is jammed with slow-moving cars, as locals cruise the avenue and its many shops and ethnic restaurants, or take in a second-run at the Logan Theatre. The Logan Square and California Blue Line stops make travel to the Loop a snap, and though there's not a lot of nightlife, the it-locales in Wicker Park and Bucktown are just a short ride away. Housing here has a wide range in price, but can be described as fair. Added bonus: apartments in the Square tend to run large, so oftentimes, you can eek out more than your money's worth.

Loop
The heart of the city, life in the Loop offers a host of amenities, including easy access to every El line, which is good, because parking a car will cost a mint. Grant Park is just a few blocks from any point and the Lake is within walking distance. Every flagship department store, from Field's to Carsons to the new Sears is in your backyard and your local library is the mammoth Harold Washington Library Center. Fine dining is a given with a raft of excellent restaurants in the vicinity and the developing theater district offers a bit of cultural nightlife. The housing stock is the glorious vintage of the twenties, thirties and forties, replete with the beautiful detail of the time. And, slowly but surely, many of these wonderful old buildings are being rehabbed, which can mean living in costly, updated luxury, or less than modern surroundings. Yes, the Loop is a bustling hub—during business hours Monday through Friday. Though thousands of people work in the Loop, not many live there, which can mean restricted hours in many businesses that cater to the workers. You'll likely have to travel over the river or into the South Loop to pick up groceries and on the weekends the area can be almost deserted as the action moves into the more affordable neighborhoods where things are open late.

Near North
Home to the Gold Coast and Streeterville, Near North has long been a desirable location for people looking to live close to the action of downtown while still having a removed space to call their own. And the proximity both to downtown and Lincoln Park has made Near North housing highly attractive, encouraging massive new condo construction as well as conversion of older buildings. For renters, this makes Near North a pricey proposition as the remaining rental units tend to be high in price—both because of scarcity and location. Though condos are frequently rented out, it's usually at a significant increase over what something might have rented for as an apartment. But, if you want to live in something new, Near North is your best bet, as every corner seems to be filled with new construction. In addition, if you like a view, the central areas are dominated by high rises, though there are still some low-rise buildings to the western edge. Near North offers numerous amenities, including easy Lakefront access, some of the city's best restaurants and most popular clubs, and proximity to the Michigan Avenue and Lincoln Park shopping hubs. The area is also dotted with other useful stores, such as Whole Foods, to serve the growing population.

Near West
In case you haven't noticed, the Near West is back with a vengeance. And as the area revitalizes, along the Lake Street warehouse corridor, the Randolph Street restaurant corridor and down by the University of Illinois, building is booming. The stock varies from older apartments in buildings near Greektown, to new multi-stories along Washington to warehouse lofts dotted throughout. The fact that the area is still in transition means renters may still be able to find a good deal in a building not yet rehabbed. Transition also means a sense of community is still developing and that amenities vary wildly dependent on where you are. Closer to the University and Little Italy and on Randolph Street, restaurants and bars abound. Along Halsted, Greektown still offers numerous options and new construction has added stalwarts like Walgreen's to the mix. In the pockets between these areas, stores can be few and far between, and further west it's a jumble of residential, empty warehouse and construction. Parking is still fairly easy, as long as you stay away from the crowded restaurant areas on weekend nights, and the area is served by buses and the Blue Line, which has an entrance at Racine and the Eisenhower as well as a brightly redone new entrance at Halsted.

Near South
After two decades of slow and steady progress toward its seeming "next big thing" destiny, the Near South Side has exploded in development over the last five years, with its boundaries expanding well beyond its traditional Roosevelt Road edge, down all the way to Cermak. Anchored by Printers Row, a charming landmark streetscape of hundred-year-old factories that became Chicago's first residential lofts, the neighborhood includes a substantial and growing stock of new construction, both high-rise and townhomes. Of the latter, Dearborn Park got it all started, and still enjoys the most central location, a garden-like oasis smack dab in the central city. More recently, the inevitable lakefront development has taken hold, with residential conversions in majestic old South Michigan Avenue buildings along Grant Park, and the massive Central Station project adjacent to Soldier Field. Longtime residents remark about the "small town in a big city" character of the neighborhood, and pet owners seem to appreciate the dog-friendly attitude. The growth of the area as a college campus center (Columbia College has shown a remarkable development that coincides roughly with its neighborhood's growth) brings a spark of youthful energy to a relatively quiet residential community that just happens to sit within walking distance of Sears Tower. Beyond the neighborhood's inherent charms, its location is a primary asset: it sits within walking distance of Grant Park and most of the city's cultural institutions, and at the hub of all the city's transportation options. Because of its downtown location, street parking can be a nightmare, and most residents lease or buy a parking space, or go without an automobile. Nightlife is quiet but developing, and Buddy Guy's Legends, Hothouse and the Velvet Lounge join the neighborhood's moderate stock of restaurants and bars in offering a respectable list of social or entertainment options. Shopping remains relatively undeveloped, although State Street is within walking distance, and both Jewel and Dominick's have recently opened large neighborhood stores.

Pilsen
A few years ago, the Utne Reader did a feature on hot places to live, and though Wicker Park/Bucktown won as the "in" area for Chicago, Pilsen was cited as the up-and-coming neighborhood. It's easy to see why: Pilsen has a large community of artists, living in the lofty and somewhat raw spaces that dominate the area, many of them in former factories owned by long-time real estate fixtures, the Podmajersky family. Most living quarters here have an industrious feel, but you can also get the cozy, nookish kind of apartment with hardwood floors that seem to permeate Chicago, some with private gardens in the back. With the dismantling of Maxwell Street and the UIC expansion encroaching, rents are slowly sneaking up, but still pretty cheap compared to most North Side areas. Buses run on the main arteries, like Halsted, Ashland, Cermak and 18th, and the Orange Line, Blue Line and Red Line all make stops at different parts of the neighborhood. For those with autos, the ever-audible Dan Ryan is nearby. The east side is a little lacking in the restaurants and bars department, but the west side offers a host of Mexican eateries and corner dives, making for relaxed and colorful nightlife.

Ravenswood
Even though your mother's voice calling you into dinner is an end to summer dreaming, it's always comforting. It's what home means. Ravenswood is that part of Chicago. It has a lot of houses, grass, trees, and kids. Around Christmas, you can see the collection of decorative lights people have put out. In summer, families go for a walk, beneath the backdrop of sprinklers. For fun, The Old Town School of Folk Music has nightly concerts. The Puppet Parlor has live puppet shows. There's the Davis Theater, which has cheap matinees. Welles Park has tennis courts and little league. There are some fine bars as well, Scott's and Benedict's. For eats, there's the Cuban restaurant, Cafe 28. Beans N' Bagels has amazing flat bread sandwiches. Zephyr's serves breakfast 24/7 and has massive ice-cream creations. Here, there is not much retail shopping. The Record Round-Up on Montrose has vinyl and a variety of fun oddities. Housing stock runs the gamut. Most apartments are older, with wood floors and hissy radiators. New buildings are being built, mostly condos, but there are several huge lofts along Irving Park and some along Damen. Parking is pretty good in this neighborhood. You don't need a parking sticker and neither do your visitors. The Brown Line El runs through most of Ravenswood and gets you downtown quickly.

Rogers Park
The city's northernmost neighborhood, in previous years Rogers Park has had a reputation for being a fairly dangerous place to live. But things improved significantly during the nineties and though there are still some areas to avoid, the attractive housing options (massive apartment buildings, large spaces, reasonable pricing), coupled with the proximity of Evanston (good shopping), amazing Lake frontage and easy transportation (via the Red Line) to downtown have drawn a growing population. The rehab boom is just picking up here, so a lot of the buildings will still tend to be "vintage," but the tradeoff is one of space. A $700 one-bedroom here is liable to offer you significantly more moving-around room than something closer to downtown, and well, vintage has character, right? And, as a whole, Rogers Park is swimming with character, playing home to numerous ethnic groups—from Latinos and Eastern Europeans to the Indian population that has kept Devon Avenue as one of the city's great food metropolises. Mix in the college populations from Loyola and Northwestern and you'll find quite a crowd in the great mix of restaurants populating the area.

Roscoe Village
The quiet, quaint residential streets of Roscoe Village offer a quieter atmosphere than the hustle and bustle of nearby Lakeview, with lower prices and less density. Though lacking the massive collection of large-scale multi-unit apartment buildings that tend to characterize the North Side, Roscoe Village instead boasts rentals in two- and three-flats where the owners frequently live downstairs and rent out their upper floors. You can still frequently find signs posting apartments for rent up and down the side streets. Though El access is further away, the area is served by numerous bus lines and offers access to downtown through various arterial streets like Western Avenue, while Interstate 94 is an easy drive. Street parking is still fairly easy to find in this area, though it tends to get more difficult the closer you get to Roscoe Street. Nightlife bustles along Roscoe and Belmont, which house numerous down-to-earth bars and restaurants. The nearby Riverview Plaza, along with easy access to newly built spots like Costco along Elston, make shopping a breeze and for antiquers, the row along Belmont through Roscoe Village features some of the city's best antique stores.

Ukrainian Village
Big, sprawling bungalows and graystone and brick three flats mark the majority of apartments available in Ukrainian Village, along with built-in-a-month condo buildings popular with the professional set. Young families and single scenesters are in abundance, enjoying the quiet, tree-lined side streets and lively nightlife provided by the several happening bars, restaurants and live-music venues. You can get an old, gorgeous apartment here, resplendent with stained glass windows, detailed woodwork and a front open-air porch, but it will cost you a bit. It's not Lincoln Park prices, but Ukrainian Village is a popular near West Side place to live, and character-filled apartments get snatched up quickly. Transportation can be a little tough; most likely, you'll have to hoof it to get to either of the nearest Blue Line stops, but buses run on Chicago, Western, Division and North at a respectable (for the CTA, anyway) rate.

Uptown
Never mind what it used to be decades ago: gangsters and glamour and all that jazz. And don't put too much faith in what it's poised to be in the future: condos and mixed-used complexes and a restored landmark theater. The Uptown of today is worth living in right now because it's one of the cheapest North Side hoods on the Lake, and, as such, it's never, ever boring. Sure, sometimes that means it's dangerous: a stroll down the grittier parts of Sheridan or Broadway proves that its rep as a dumping ground for the down-and-out is still warranted. But stay a little longer and you'll glimpse Buddhist monks, hidden mansions and foxy Bosnian cashiers. Leather daddies. Vietnamese groceries and African restaurants. Fully-shrouded Muslim wives. Gay brunchers. Russian Jews. Green Mill swing dancers. Undercover cops. People who drive Jaguars—and people who see jaguars. If the place was any spiffier, the residents who make Uptown so interesting probably couldn't afford to stay. With four Red Line stops, countless buses (including some fabulous expresses), a big fat Jewel, proximity to Wrigleyville nightlife and the beach, as well as lots of early twentieth-century dwellings (many with hardwood floors and residual character), it's little wonder why reasonable rents here are starting to rise.

Wicker Park
If the so-called trailblazers of Wicker Park—the white kids who moved there nine years ago when it was borderline ghetto (you know who they are, and if you don't, they'd love to tell you about it)—didn't see the neighborhood's explosion coming, they were kidding themselves. And though you're still likely to see a gang activity in your backyard, the neighborhood's West Side location marks one of the city's perfect places to live: its proximity to downtown (ten minutes, max) is ideal, as is its striking distance to anywhere else you want to be on the North Side (Lakeview, Lincoln Park, Humboldt Park, Logan Square, etc). Though its gentrification has evoked a cry of foul from, well, mostly the area's white residents, it's worth noting that throughout Wicker Park proper (the area surrounding the Park itself, on both sides of Damen, and a little further south), many of the original homeowners remain—they just rent out their top two floors for huge sums. Although the Wicker Park nightlife attracts residents, despite the fact that restaurants tend to be more high end, its breadth is still not that of Lakeview or Lincoln Park.