The 13 Coolest Neighborhoods in Chicago: Trendy Faves in the Windy City

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 abundance of cool neighborhoods this Midwestern hub has to offer. But if you’re preparing to move to the Windy City, you’re about to learn much more about the coolest neighborhoods in Chicago and what living there is really like.

Planning a move to the Windy City? Start by getting a quote from PODS.

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 that are home to iconic works of art (hello, Art Institute of Chicago) and incredible dining 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 the city consistently wins awards like its eight-year run as “best big city in America” — 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.  

Finding the Coolest Neighborhoods in Chicago to 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? What are the best neighborhoods in Chicago for families? 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: What is the hipster area in Chicago? A: Chicago is a hipster city, no question. And some of the coolest neighborhoods in Chicago (like Wicker Park) have landed on lists of the most hipster places. Logan Square is another area that hits the hipster neighborhood meter. But the city’s massive footprint and diversity of neighborhoods means Chicago 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): $2,150
• Average home value: $490,300
• Great for: Young professionals, coffee shop regulars, hipsters

To start off our guide to the coolest neighborhoods in Chicago, 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. 

This 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 The Logan Theatre — 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 the best hipster neighborhood Chicago has to offer in the 2012 sense — that is, beanies and skinny jeans — you probably won’t find it 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 coolest neighborhoods in Chicago for hipsters.

2. Andersonville

• Average rent (one-bedroom): $1,825
• Average home value: $526,500
• 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’s nice neighborhoods. It’s closer to suburbs like Evanston than it is to Millennium Park, after all — which for some, makes it one of the best neighborhoods in Chicago for young adults looking for cheaper housing. 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 Swedish American Museum, for instance, and pay homage to the Swedish immigrants who settled in Andersonville in the 1800s. 

In June, watch the street bloom with flower crowns and live music when Midsommarfest 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,” according to Andersonville Chamber of Commerce.

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.
(Source: Richard Tao via Unsplash)

3. The Loop

• Average rent (one-bedroom): $2,850
• Average home value: $268,300
• 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 $2,850 for about 821 square feet), but you’ll find plenty of residents and sightseers alike in this fun neighborhood in Chicago, roaming around the waterfront, weaving through the business district, snapping photos from the glass observation deck atop Willis Tower. If you love people-watching, it’s one of the best downtown Chicago neighborhoods for it — just take a seat near Cloud Gate. 

And let’s not forget Lollapalooza, the massive multistage music festival that reverberates across Grant Park every summer with world-famous bands — all performing 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, all of the coolest neighborhoods in Chicago are vibrant and culturally rich. But if you’re looking for an area filled with art museums, murals, and rich cultural influences, don’t sleep on Pilsen, an artsy, tasty, affordable hub of Chicago’s Mexican-American population.

4. Pilsen

• Average rent (one-bedroom): $1,850
• Average home value: $435,600
• Great for: Artists, foodies, family-owned businesses

Southwest of Downtown, Pilsen is the place for art aficionados to be. The neighborhood features creative highlights like the National Museum of Mexican Art, with its Mexican textiles, paintings, photography, and more — and admission is always free. 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 delicious spots for tacos, chorizo breakfast burritos, margaritas, sweet empanadas, and so much more. 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 the most underrated Chicago neighborhood, locals bring up Rogers Park repeatedly. Situated by the lakefront, 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 diverse population to its wide-ranging dining options, bustling arts district, and lakefront location, it’s worth looking slightly farther out from the city center to Rogers Park.

As the first officially recognized gay neighborhood in the U.S., Northalsted has long been (and still is) one of the trendiest neighborhoods in Chicago.
(Source: Northalsted via Facebook)

5. Northalsted

• Average rent (one-bedroom): $2,050
• Median home sale price: $394,000
• 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) among the coolest neighborhoods in Chicago is rich with small businesses, nightlife, rainbows, and, of course, pride. Northalsted was the first gay neighborhood officially recognized by a large U.S. city, back in 1997. Today, the LGBTQ+ community remains hugely important culturally, politically, and economically. Whether you’re looking to learn about LGBTQ+ history while strolling along Legacy Walk, or let loose at KitKat’s during the city’s best drag brunch, this neighborhood has you covered. 

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 Sidetrack, a two-story, six-room bar (with a rooftop) to sing along to your favorite music videos and get a frozen drink; or take to the Kit Kat Lounge and Supper Club, a campy stronghold for drag shows and boozy brunches.

6. Ukrainian Village

• Average rent (one-bedroom): $2,700
• Average home value: $534,200
• Great for: Families, young professionals, neighborhood feel, Ukrainian culture

Situated just south of Wicker Park, this small (about two square miles) borough has a feel distinct 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 neighborhoods in Chicago (and one of the most artsy and hip neighborhoods in Chicago): You can support a local Ukrainian-owned business (the Chicago area is home to the second-largest Ukrainian and Ukrainian-American population in the U.S.; take in some art at the Ukrainian Institute of Modern Art or the Ukrainian National Museum; catch an alternative music show at the Empty Bottle; or enjoy a farm-to-table Northern Italian meal at A Tavola. 

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.
(Source: Fulton Grace Realty via Facebook)

7. River North

• Average rent (one-bedroom): $3,175
• Average home value: $321,400
• 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 largest concentration of art galleries outside of Manhattan. There are works imported from Asia to masterpieces painted locally in Chicago — and you can travel around the art world by visiting them all. 

You’ll find tons of trendy restaurants, shops, and clubs to go around, too, plus gorgeous venues like the House of Blues Chicago, 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): $2,275
• Average home value: $291,500
• Great for: Foodies, families, young professionals

West of Millennium 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 Mediterranean-meets-Midwestern fare at Avec. 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 nearly $3,075 for a one-bedroom apartment. Situated on the water, just north of Millennium Park, this Near North Side neighborhood boasts sleek, luxury condo buildings in a nice part of Chicago. 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 coolest neighborhoods in Chicago.

9. Wicker Park

• Average rent (one-bedroom): $2,800
• Average home value: $663,500
• 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 lovingly amassed coffee mugs or vintage records in your carefully curated collection, Wicker Park may be the place for you. This hip residential area is brimming with cafes, taprooms, vintage boutiques, and so much more, making it one of the coolest neighborhoods in Chicago worth considering. Slide over to The Wormhole 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 Emporium, 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 The 606, 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. The path definitely ranks Wicker Park as one of the best Chicago neighborhoods to walk around.

Q: What is the trendiest neighborhood in Chicago? A: When it comes to development, Chicago’s West Loop neighborhood is 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. Logan Square also makes the cut, with “Hipster Highway” (Milwaukee Avenue) home to a changing menu of trendy bars and restaurants.

10. Old Town

• Average rent (one-bedroom): $2,800
• Average home value: $387,300
• 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 iconic improv comedy club and academy The Second City lives in Old Town — the jumping-off point for comedians ranging from Gilda Radner and Bill Murray to Tina Fey, Jordan Peele, and Stephen Colbert. You can also catch a show and plenty of laughs at other local haunts, such as Zanies Comedy Club, making Old Town one of the best neighborhoods to live in Chicago for comedy fans.

Q: Is Chicago safe?  A: That depends on where you live. Overall, the Windy City doesn’t score well on the NeighborhoodScout crime index: A 5 for 2025. For more details on safety in the Second City, check out our article on where to find the Safe Neighborhoods in Chicago.

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

11. Avondale

• Average rent (one-bedroom): $1,625
• Average home value: $470,100
• 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. The neighborhood's eclectic mix of businesses, from a self-proclaimed “horror-themed coffee shop” to a museum dedicated to insects, make it one of the most fun (and cute!) neighborhoods in Chicago for curious kids and bug-lovers. Gentrification is encroaching, for sure, but it’s still safe to say Avondale is one of the best neighborhoods in Chicago — and belongs near the top of any list of trendy neighborhoods in Chicago.

Q: What is the coolest neighborhood in Chicago? A: Any one of the neighborhoods on our list could take the top spot for coolness in the Windy City. But if we had to pick one, we’d go with an up-and-comer: Avondale. Housing is still relatively affordable, which is attracting artists and young families. And as the former hub for Chicago’s Polish immigrants, traditional spots like Andy’s Deli add to the cool factor as much as the influx of galleries and destinations like the retro Avondale Bowl — a combo bar, bowling alley, and art space.

12. Streeterville

• Average rent (one-bedroom): $3,075
• Average home value: $343,400
• Great for: Families, outdoor activities, nightlife

When considering the coolest neighborhoods in Chicago to explore, you won’t want to miss out on Streeterville. Just east of River North and north of Millennium Park, the family-friendly neighborhood is home to many young professionals and retirees alike. According to Niche, Streeterville ranks No. 8 among the best places to live in Chicago in 2025 (and the second best neighborhood for young professionals), thanks in part to its above-average public schools, central location, and variety of fun things to do. 

For instance, check out lakefront Navy Pier, 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 Museum of Contemporary Art Chicago, and of course, shop along The Magnificent Mile, 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 rich with history, thanks to iconic architecture from Frank Lloyd Wright. It’s also home to the Obama Presidential Center, a 19-acre neighborhood gem honoring and furthering the work of former President Barack Obama and First Lady Michelle Obama — a proud Southside Girl.

13. Hyde Park

• Average rent (one-bedroom): $1,775
• Average home value: $240,600
• 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. It’s the Chicago neighborhood Barack and Michelle Obama once called home. But it’s also where you’ll find the Frederick C. Robie House, a Frank Lloyd Wright-designed building that is now a designated UNESCO World Heritage Site and a house museum owned by the University of Chicago — and it’s 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 Midway Plaisance Park will take you through nearly 72 acres of urban oasis, including an ice rink (Yes, you can take skating 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 No. 3 among the best places to live in Chicago for families. 

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

Let PODS Help You Move to One of the Coolest Neighborhoods in Chicago

Now that you know where to find the coolest neighborhoods in Chicago, it’s time to start planning your move! Have a PODS portable storage container delivered right to your driveway for convenient packing and loading. When you’re ready, your container will be picked up and transported to your new Chicago home, or — if you need more time — it can be stored in a secure PODS storage facility for as long as you need. One month of storage is built into every PODS move, so you can be flexible with your timeline.

Learn more about what life is like in the Windy City, right here on the PODS Blog.

Sofia Rivera is a Brooklyn-based lifestyle editor and frequent contributor to the PODS 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.

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

Editor’s note: Average and median rent prices were obtained from RentCafe; average home values were obtained from Zillow. For ease of reading, monthly rental prices were rounded to the nearest $25 and home values were rounded to the nearest $100.