Chicago Guide Series: The Neighborhoods of Chicago

Oh, Chicago. I’ve lived here for 4 years and couldn’t love this city any more. Piggybacking off of the success of my Phoenix and Scottsdale, Arizona guide, I thought I’d start a new guide series: CHICAGO!

Chicago is often called “the city of neighborhoods.” And it’s for good reason–the neighborhoods in Chi Town are diverse and plentiful, and each one has something different to offer. While I can’t possibly cover all of them (there are seriously SO MANY), here are some of my favorite neighborhoods to explore:

The ultimate guide to Chicago
A really old pic from one of my favorite days ever in Chi town

The Loop

Chicago’s downtown neighborhood is called The Loop because of how the L trains run around it (forming, you guessed it, a loop). Everything business is down here, including my job! People don’t tend to spend a lot of time down here on the weekends; I’d compare it to the financial district of Manhattan. However, here’s where you’ll find some of the most recognizable Chicago landmarks: the Bean and Millennium Park, and the Art Institute of Chicago. You’ll also find most of the theaters of Chicago, including the Chicago theater, the Oriental theater, etc.

The ultimate guide to Chicago

River North

River North is called that because it’s directly North of the river. I know, we have some REALLY unique neighborhood names! River North is a more posh area of town–lots of high rises and fancy restaurants. It’s perpendicular to the famous Michigan Ave, and a lot of my restaurant recommendations are in that neighborhood. Most people will say that River North is as close to Manhattan as Chicago gets.

Gold Coast

The Gold Coast is a pretty small neighborhood, but full of charm. Think: million dollar homes, trendy bars and restaurants, and super swanky shopping.

Old Town

Old Town Chicago is, for the most part, a strip of bars, restaurants, and shops along Wells Street. Wells is a very charming street, and one of my favorite places to take out of town guests. It’s also home to The Second City, the famous comedy center!

Lincoln Park

Lincoln Park is just the cutest. Lots of families and students (DePaul is in this neighborhood), and plenty of restaurants and bars. One of the best things to do is to walk up Clark street and just explore. I also highly recommend walking through the park and the zoo (pictured above) for the best views!


If you walk far enough up Clark St from Lincoln Park, you’ll hit Lakeview. I used to live in Lakeview, and I can’t say enough good things. First thing you need to know: Lakeview is HUGE. It actually comprises multiple mini neighborhoods: Wrigleyville (where Wrigley field and some crazy rowdy bars are), Boystown, Roscoe Village, Southport, and East Lakeview. If you visit over Pride weekend you might just catch the Pride parade (pictured above)!

I lived in East Lakeview, but frequented Southport Corridor on weekends. Walking around Southport has always been one of my favorite activities.

Wicker Park/Bucktown

Wicker Park is one of our more interesting neighborhoods (but it’s gentrifying pretty quick). You can go vintage shopping on Milwaukee Ave, or do some fancy shopping on Damen Ave. There are some amazing restaurants and bars, and you could easily spend all day in this neighborhood.

Logan Square

Logan Square is a super up and coming neighborhood that is home to many fantastic restaurants and cocktail bars. It’s always a treat for me to get over there and if you’re looking for an off-the-beaten-path neighborhood to get cocktails in, this is it.

The ultimate guide to Chicago


Pilsen is a traditionally Hispanic neighborhood that has a TON of flavor. There are some really great restaurants there, and it’s just fun to walk around and soak up the culture.


A bit off the beaten path (at least for visitors), Andersonville is Northwest of Lakeview. They have a lot of local stores and restaurants, and I love walking around there and exploring!

Hyde Parke

Probably best known to visitors as being Obama’s home, Hyde Park is also home to the University of Chicago. It’s one of the most gorgeous college campuses I’ve ever seen, and it’s absolutely worth a visit. It’s also home to the Museum of Science and Industry if you’re headed there anyway!


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Where to Eat in Chicago
Weekend Guide to Chicago
The Best Ice Cream in Chicago
What to Buy for a Chicago Winter
3 Years in Chicago