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If you’ve only visited or Googled Chicago, you might know the Illinois city for its mouthwatering deep-dish pizza or perhaps the giant, mirrored Bean ripe for taking selfies with the city skyline in Millennium Park. And even that small peek into the city may be enough to clue you into the fact that there are so many cool neighborhoods in Chicago. But if you’re preparing to move to the city, you’re about to learn much, much more about all the coolest Chicago neighborhoods this midwestern hub has to offer. 

Planning a move to the Windy City? Start by getting a quote from �Ӱ�Pro.

Chicago is the third-largest city in the U.S. by population, comprises no fewer than 77 neighborhoods, and encompasses 234 square miles of land. Needless to say, there’s a lot of Chicago to explore. From museums with art you’ve seen in textbooks (hello, ) and incredible eats all around town to free concerts in the park and a rollicking comedy scene, there’s no shortage of things to do. And that’s precisely why it consistently wins awards like “” — there’s just so much to love. But to narrow down the search, let’s take a look at some of the best neighborhoods in Chicago.  

What Chicago Neighborhood Should I Live In?

For newcomers, parsing all of the square mileage can be overwhelming. Your head may be full of questions like: Where exactly are the coolest Chicago neighborhoods? What are the best Chicago neighborhoods? Which one may be the best fit for me? While living in Chicago means incredible access to 77 enclaves that are no doubt all cool in their own right, here are the ones that top our charts for cool neighborhoods in Chicago. As we dive into this guide, we’ll point out helpful information such as average rent prices, home values, cultural influences, and fun things to do in some of the best neighborhoods to live in Chicago to help you hone in on the area that best fits your lifestyle. 

Without further ado, here’s an easy reference list of the best places to live in Chicago to help you answer the most pressing of all questions: What Chicago neighborhood should I live in?

Q: Is Chicago a hipster city? A: In a word, yes. Chicago is a hipster city. Certain cool Chicago neighborhoods () have landed on lists of most hipster places, and about how to assimilate as a hipster in Chicago. But its massive footprint and diversity of neighborhoods means the city has so much more to offer than just one stereotype — you’ll find all kinds of cool in the Windy City.

Logan Square is a hipster neighborhood in Chicago that gets better the more time you spend there. Only have a few hours? Head down Milwaukee Avenue and stop into the many cafes and shops that line “Hipster Highway.”

1. Logan Square

• Average rent (one-bedroom):
• Average home value:
• Great for: Young professionals, coffee shop regulars, hipsters

To start off our Chicago neighborhood guide, let’s talk about Logan Square. If your idea of a perfect Saturday involves an oat milk latte, some incredible vintage thrift shopping, and a night that ends in craft cocktails and dancing, you should make your way over to Logan Square, one of the many cool neighborhoods in Chicago. 

The West Side neighborhood is well known for its thoroughfare, Milwaukee Avenue (which you may even hear called “Hipster Highway”), where you’ll find gems such as — a 1915-built institution with an Art Deco look that screens old and new flicks and is equipped with a full bar. Stroll along Milwaukee and you’ll also see tons of bars, cafes, music venues, and galleries, along with the Illinois Centennial Monument and its surrounding Logan Square Park. 

Q: What is the hippest neighborhood in Chicago? A: That depends. If you’re looking for Chicago hipster neighborhoods in the 2012 sense — that is, beanies and skinny jeans — you probably won’t find them anywhere. But if you’re looking for genuinely cool record shops, incredible vintage thrift finds, and trendy coffee shops and cocktail bars, Logan Square or nearby Wicker Park are a couple of the best Chicago neighborhoods for hipsters.

2. Andersonville

• Average rent (one-bedroom):
• Average home value:
• Great for: Families, young professionals, shop-local enthusiasts

Situated in west Edgewater, this community may feel pretty far from the buzz of downtown if you’re looking at a map of Chicago neighborhoods. It’s closer to suburbs like Evanston than it is to Millennium Park, after all. But take an amble down Clark Street, the area’s main drag, and you’ll find plenty of reasons to make this North Side community your home. You can tour the , for instance, and pay homage to the Swedish immigrants who settled in Andersonville in the 1800s. 

In June, you can watch the street bloom with flower crowns and live music when takes over a section of Clark Street for a weekend. And all year long, you can shop an abundance of local businesses along the street and around the neighborhood, which hosts “the largest network of local and independent businesses in the area,” .

If you’re looking for neighborhoods in downtown Chicago, you can’t miss The Loop, best known for iconic scenes such as Millennium Park (with the recognizable mirrored Bean) and the Chicago Riverwalk.
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3. The Loop

• Average rent (one-bedroom):
• Average home value:
• Great for: Commuters, young professionals, sightseers

If you look up a picture of Chicago, The Loop is probably what you see. Right on the Lake Michigan waterfront, the downtown area is where you’ll find iconic scenes such as Millennium Park (with the recognizable mirrored Bean) and the Chicago Riverwalk. It’s one of the downtown Chicago neighborhoods and it’s a small area, only about 1.5 square miles, but it’s packed with businesses. 

You may not find many families living there, given its comparatively steep rental rates (an average of around $2,775 for about 821 square feet), but you’ll find plenty of residents and sightseers alike roaming around the waterfront, weaving through the business district, snapping photos from the glass observation deck atop Willis Tower, or boarding the elevated “L” train. If you love people-watching, it’s one of the best downtown Chicago neighborhoods for it — just take a seat near . 

And let’s not forget , a massive nine-stage music festival that reverberates across Grant Park each August, where world-famous bands perform against the backdrop of the Chicago skyline. When it comes to postcard-worthy views, this is surely one of the coolest Chicago neighborhoods.

Q: What is the most vibrant neighborhood in Chicago? A: Truth is, Chicago is full of vibrant neighborhoods to explore. But if you’re looking for an area filled with art museums, murals, and rich cultural influences, don’t sleep on Pilsen, which has also been dubbed one of the coolest Chicago neighborhoods.

4. Pilsen

• Average rent (one-bedroom):
• Average home value:
• Great for: Artists, foodies, family-owned businesses

Southwest of Downtown, Pilsen is the place for art aficionados to be. It’s home to the , which features Mexican textiles, paintings, photography, and more, and admission is always free. Not only that, but all over the neighborhood, you’ll find colorful murals adorning the sides of buildings. Once home to many Eastern European immigrants, the enclave is now home to a large Mexican-American population, and the Latinx influence shows through the neighborhood’s for tacos, chorizo breakfast burritos, margaritas, sweet empanadas, and so much more. 

Forget the limits of Chicago — Forbes named Pilsen one of the in 2018. If you’re looking for a place full of culture with relatively affordable rent, Pilsen is one of the best neighborhoods to live in Chicago.

Q: What is the most underrated neighborhood in Chicago? A: When asked to sound off about which is the , locals bring up Rogers Park over and over again. Situated by the water, just north of Edgewater and 10 miles north of Millennium Park, the area may be a bit of a commute but it’s still accessible by the Red Line (though it’ll take you about an hour). From its to its wide-ranging dining options, bustling arts district, and lakefront location, it’s worth looking slightly further out from the city center to Rogers Park.

As the first officially recognized gay neighborhood in the U.S., it’s not hard to see why Northalsted deserves mention as one of the trendy neighborhoods in Chicago — the subsection of Lakeview is a trendsetting enclave by nature.  
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5. Northalsted

• Average rent (one-bedroom):
• Median home sale price:
• Great for: LGBTQ+ community, nightlife, small businesses

Formerly known as Boystown, this recently renamed enclave (a portmanteau of North Halsted, the street that creates the neighborhood’s western border) was the by a large U.S. city back in 1997. Today, the LGBTQ+ community remains hugely important. Whether you’re looking to or learn about LGBTQ+ history while strolling along , the subsection of Lakeview is rich with small businesses, nightlife, rainbows, and, of course, pride.

Q: Which Chicago neighborhood is known for its vibrant nightlife? A: If you want a late night out in one of the cool neighborhoods in Chicago, take the L to Northalsted. Head to , a two-story, six-room bar (with a roof) to sing along to your favorite music videos and get a frozen drink; or take to the , a campy stronghold for drag shows and boozy brunches.

6. Ukrainian Village

• Average rent (one-bedroom):
• Average home value:
• Great for: Families, young professionals, neighborhood feel, Ukrainian culture

Situated just south of Wicker Park, this small (about two square miles) borough has a distinct feel from its trendy northern neighbor. The brick rowhouses, multi-family inhabitants, and tree-lined streets create a residential vibe, but don’t think that means there’s nothing to do in Ukrainian Village. 

On the contrary, it’s one of the coolest Chicago neighborhoods (and one of the artsiest neighborhoods): You can support a local Ukrainian-owned business (the Chicago area is home to the second-largest Ukrainian and Ukrainian-American population, according to the ); take in some art at the or the ; catch an alternative music show at the ; or enjoy a farm-to-table Italian meal at . 

River North belongs on any list of the coolest Chicago neighborhoods. Its extremely high concentration of art galleries and bumping nightlife make it one of the notable hip neighborhoods in Chicago.
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7. River North

• Average rent (one-bedroom):
• Average home value:
• Great for: Artists, singles, nightlife

Chicagoans who are single, love art, and are looking to mingle should take their stylish selves over to River North. The Near North Side neighborhood is known for its abundance of architecture, art galleries, and chic nightlife. In fact, it’s said to claim the — from exhibits of works imported from Asia to masterpieces painted locally in Chicago, you can travel around the art world by . 

There are tons of trendy restaurants, shops, and clubs to go around, too, plus gorgeous venues like the , an opulent concert hall modeled after an opera house in Prague

Q: What is the most beautiful neighborhood in Chicago? A: Beauty is in the eye of the beholder, of course, and from architecture to green space, each of Chicago's 77 neighborhoods offers up a unique kind of beauty. If you’re looking for those iconic Windy City vistas, though, you’d be remiss not to go to the Loop, where you can see the city skyline reflected in Millenium Park’s Cloud Gate (“the Bean”) or from the observation deck atop Willis Tower.

8. West Loop

• Average rent (one-bedroom):
• Average home value:
• Great for: Foodies, families, young professionals

West of Millenium Park, this Chicago neighborhood looked pretty different a decade or so ago — a former meatpacking district, the vibe was decidedly industrial. These days, rapid development (read: frequent construction) has transformed the area into a hotspot for modern eateries with sought-after reservations and high-rise condo buildings. 

Be sure to dine out on Restaurant Row on Randolph Street, treating yourself to some delicious . And while living in West Loop may mean tolerating some construction, it comes with the perk of easy access to each new restaurant that opens its doors. 

Q: What is the posh area of Chicago? A: If you equate poshness with price point, Streeterville is the Chicago neighborhood with the highest average rent price, at . Situated on the water, just north of Millenium Park, the Near North Side neighborhood boasts sleek, luxury condo buildings. If you’re looking for a plethora of art galleries or high-end restaurants, River North and West Loop are also some of the nicest neighborhoods in Chicago.

If you like quirky coffee shops, arcade bars, and hipster vibes, you’ll love Wicker Park, one of the very cool neighborhoods in Chicago.

9. Wicker Park

• Average rent (one-bedroom):
• Average home value:
• Great for: Young professionals, vintage shopping, nightlife

If, when packing your bags for your move to Chicago, you find yourself unable to part with any records in your carefully curated collection or lovingly amassed coffee mugs, Wicker Park may be the place for you. The hip residential area is brimming with cafes, taprooms, vintage boutiques, and so much more, making it one of the cool neighborhoods in Chicago worth considering. Take to for a freshly brewed pour-over and a serving of 80s nostalgia (peep the “Ghostbusters” poster on the wall, along with other memorabilia). 

Keep the throwback vibes going that night at , an arcade bar with all the classics, from air hockey and Austin Powers-themed pinball to Centipede and Galaga. Looking to spend some time in some of Chicago’s prized green space? Head over to , an abandoned railway that’s been reimagined as a 2.7-mile paved path bordered by greenery, where walkers, bikers, and runners can get an elevated view of the city below. It runs through the north side of Wicker Park and also touches nearby neighborhoods such as Bucktown, Humboldt Park, and Logan Square.

Q: What is the trendiest neighborhood in Chicago? A: When it comes to development, Chicago’s West Loop neighborhood is rapidly evolving, making it among the many nice neighborhoods in Chicago. Formerly an industrial meatpacking district, the neighborhood now boasts a slew of luxurious high-rise residential buildings and Michelin-starred restaurants that call in foodies from all around the city.

10. Old Town

• Average rent (one-bedroom):
• Average home value:
• Great for: Families, comedy lovers, green space

East of Wicker Park and north of River North, Old Town boasts incredible green space in the nearby Lincoln Park, quick access to Lake Michigan, and a lovely residential vibe. Keep your ears open as you walk around and you may just hear a punchline or two: The incredibly famous improv comedy club lives in Old Town and has been a jumping off point for comedians ranging from Gilda Radner and Bill Murray to Jordan Peele and Tina Fey. You can also catch a show and plenty of laughs at other local haunts, such as , making Old Town one of the best neighborhoods to live in Chicago for comedy fans.

 Ask almost anyone and they’ll tell you Avondale is one of the cool neighborhoods in Chicago — and one that feels equally welcoming to young professionals and families alike. 
(Source: )

11. Avondale

• Average rent (one-bedroom):
• Average home value:
• Great for: Families, young professionals, quirky things to do

The coolness of any place is such a subjective metric, but when there’s so much consensus around one spot, you can’t help but listen. Such is the case for Avondale, which, in 2022, won a spot on Time Out Magazine’s survey of the 51 . They polled more than 20,000 urbanites around the globe to make the list, and Chicago’s Avondale rang in at number 16. 

Time Out touts the neighborhood's eclectic mix of businesses, from a self-proclaimed “” to a , any curious child or bug-lover's dream come true. “Avondale is a rare place that feels equally welcoming to families, arty twenty-somethings, and working-class Chicagoans,” writes Time Out Chicago editor Emma Krupp. “And as the neighborhood deals with rising rents and other symptoms of gentrification, community organizations are hard at work to make sure it stays that way.” Safe to say it’s one of the best neighborhoods in Chicago — and belongs near the top of any list of trendy neighborhoods in Chicago.

12. Streeterville

• Average rent (one-bedroom):
• Average home value:
• Great for: Families, outdoor activities, nightlife

When considering Chicago neighborhoods to explore, you won’t want to miss out on Streeterville. Just east of River North and north of Millenium Park, the family-friendly neighborhood is home to many young professionals and retirees alike. , Streeterville is one of the best places to live in Chicago (and the ), thanks in part to its above-average public schools, central location, and variety of fun things to do. 

For instance, check out lakefront , where you can take a spin on a giant ferris wheel, navigate a funhouse maze, catch live shows, and so much more. You can also appreciate modern art at the , and of course, shop along , the trendy shopping district that runs along the western edge of the neighborhood. 

Q: What is the nicest neighborhood in Chicago? A: If green space, skyline views, and a family-friendly atmosphere sound nice to you, don’t sleep on Hyde Park. This South Side neighborhood is also filled with history, thanks to famous architecture from Frank Lloyd Wright and previous denizens such as Barack Obama.

13. Hyde Park

• Average rent (one-bedroom):
• Average home value:
• Great for: Families, outdoor activities, nightlife

When speaking of the artsiest neighborhoods in the Windy City, we’d be remiss not to bring up Hyde Park. Architecture buffs, history fanatics, and art lovers will thrive here. For instance, it’s the Chicago neighborhood Barack and Michelle Obama once called home. But it’s also where you’ll find the , a Frank Lloyd Wright-designed building that is now a designated and a house museum owned by the University of Chicago and open to visitors. 

What is most likely to affect your day-to-day experience living in Hyde Park, though — and what makes it one of the many cool neighborhoods in Chicago — is the abundance of green space. A stroll in will take you through nearly 72 acres of urban oasis, including an ice rink (yes, you can take lessons!), gardens, and sports fields. The park also hosts special events such as a summer concert series and outdoor movie showings. It’s not hard to see why Niche ranks it among the . 

If views are what you’re after, though, head to a Hyde Park gem: . The man-made lakefront peninsula park offers gorgeous skyline views — as well as , if you have a keen eye.

Let �Ӱ�Pro Help You Move to One of These Cool Neighborhoods in Chicago

Okay, now that you have an idea of the coolest Chicago neighborhoods (and hopefully a better idea of where to live in Chicago), it’s time to pack! (And if you’re looking for motivation, be sure to peruse the �Ӱ�Pro Blog for helpful tips on moving and packing.) Thankfully, moving with storage makes for a flexible move. If you’re not sure where in Chicago you want to put down roots — how to decide between proximity to amazing vintage shopping or the Lake Michigan waterfront?! — you can give yourself time to get to know the city and which area best fits your vibe by renting a place short term. Bring what you need with you and pack the rest into a �Ӱ�Pro portable moving and storage container. Keep it at a �Ӱ�Pro Storage Center as long as you want and, when you’ve found your perfect place, have it delivered right to your new home. Easy!

Sofia Rivera is a Brooklyn-based lifestyle editor and frequent contributor to the �Ӱ�Pro Blog. Her work has appeared in Boston magazine, Apartment Therapy, and more. You can most often find her redecorating her apartment, trying out a new recipe, or trekking all over the city.

Editor’s note: For ease of reading, monthly rental prices were rounded to the nearest $25 and home values were rounded to the nearest $100.

(Source for image featured at top: Joel Mott via Unsplash)