Chicago, Illinois

Italian Beef

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The Area

If you’ve never been to the Chicago Metroplex you may not know it stretches across the southwest side of Lake Michigan. While Chicago ain’t a coast it for sure is a beach town. The Lake is a defining characteristic as it provides play in the warmer months and brings the wind in the winter.

The city is surrounded by many quiet and some city-like suburbs, some of the most beautiful in the country. Evanston, home to Northwestern University, sits north of the city along the lake and is a wonderful college town for those who crave a city, but don’t want to live in THE city. The northern suburbs tend to be a bit fancier as their lake access is rewarded with higher prices and fancier digs. To the west lie countless booming ‘burbs like Oak Park, Hinsdale, Downers Grove and Naperville, that tend to serve both upper and middle/working class families.

The Neighborhoods

As was noted above, Chicago neighborhoods are a big deal to locals. It may be the sporting culture that brings that local pride and spirit down to the street level, but it plays out for the most part innocently with the possible exception of the North Side v. South Side rivalry. Historically the North Side was wealthier and more white, and the South Side more working class and African-American. While some of that hegemony still exists, Chicago has diversified in ways that make the distinction less clear and perhaps idealistically less important.

Overall, city neighborhoods are organized into districts, and while there are plenty of exceptions for any of these characterizations you can think in terms of the north as being “posh”, downtown as urban upscale, west as hipster, and south as home to great arts, sports, historic culture and more diversity.


Young Professionals

Chicago has so many neighborhoods for young professionals it feels greedy for them not to share with other midwestern cities. Huge apartment skyrises downtown, big brick apartment buildings in the surrounding neighborhoods like Lincoln Park, three-decker apartment homes in historic and upcoming neighborhoods like Wrigleyville, and Logan Square, that all provide relatively inexpensive housing (compared to NYC/SF/LA) for the younger generations. Every one of these neighborhoods has a great local social scene if you just feel like walking out for some fun, and the L provides super-cheap transport to the rest of the city when you feel like venturing farther.

  • Downtown / The Loop
  • Logan Square
  • West Town (Ukranian Village, East Village, Wicker Park, Pulaski
  • River North
  • Lake View (Wrigleyville/Boystown)



The biggest and most famous of the LGBTQ+ neighborhoods in Chicago is Boystown. It hosts the Pride Parade and is full of cool boutiques, coffee joints, theaters, comedy clubs and amazing nightlife. Boystown, which is part of the Lakeview area also has the historical Legacy Walk the world’s only outdoor LGBTQ history museum.
Another popular neighborhood is Andersonville. Labeled “Girlstown” due to a big and growing lesbian population, the neighborhood is on the north side of the city with most of the social scene between Clark Street and Ashland Avenue. Andersonville is home to Women and Children First, one of the largest feminist and LGBTQ+ bookstores in the United States.

  • Boystown (Lakeview)
  • Girlstown (Andersonville)
  • Pilsen



Chicago has plenty of neighborhoods for young families looking for “city life” but who also demand great schools, safe streets and some of the amenities they’d get in a suburb but without you know, “the suburbs”. Beverly is a great example of these neighborhoods - big brick homes with room to grow at reasonable prices, great local schools for the little ones, and tons of outdoor space including a 250 acre forest preserve for hiking, or sledding when the snow falls. If you’re in the family way but intent on hanging in the city you’re going to be ok here.

  • Beverly
  • Edison Park
  • Lincoln Park
  • North Center
  • West Loop
  • Hyde Park

Sauganash/Forest Glen


A lot of bigger families in Chicago flock to the suburbs for the homes, yards, public schools and lifestyle, but staying in the city is absolutely a thing here as well. Neighborhoods like Sauganash/Forest Glen are magnets for families prepared to spend bigger bucks for beautiful older homes, large yards (for the city), and close proximity to great schools for their beans. It should be noted that these neighborhoods tend to be a bit quieter, with less of a jumping social scene than the hipster or younger family options but there are golf courses if that is your scene. As with most cities Chicago has plenty of “crossover” cities that attract young professionals, young families, and bigger/established families. Lake View, which includes Wrigleyville and Boystown, and Lincoln Park, are two of these areas. Great big homes, luxury condos, apartment buildings and fancy-ish amenities make these neighborhoods work across nearly all demographics, as long as you’ve got the $$$.

  • Sauganash/Forest Glen
  • Lake View (Wrigleyville/Boystown)
  • Lincoln View