It can feel overwhelming to find a Chicago neighborhood that checks all the boxes. Affordable, family-sized housing is hard to come by, especially if you need good transit options. New condos are shrinking in square footage. And those historic brick two-flats and Prairie School homes? They’re snatched off the market as soon as they list.
That’s where we come in. Whether you’re an eager homebuyer dreaming of a greystone or a renter hoping to finally live on your own, Curbed Chicago has searched high and low to bring you the best neighborhoods to consider in 2020.
Places like Bridgeport are affordable, with plentiful choices for both renters and buyers. Beverly is a homeowner’s dream, full of big yards and charming Carpenter Gothic homes. And spots like Humboldt Park are ideal for renters who need greenery. Skip the pricey, crowded ’hoods like River North and Lakeview—this list prioritizes communities with great transit, parks, and affordability.
In these seven neighborhoods, you’ll have the best chance of finding what you need right now—and maybe even discover a new place to love.
The draw: Unbeatable prices for both renters and buyers
Similar neighborhood: McKinley Park
Don’t miss: Palmisano Park
In this residential, walkable neighborhood on the Southwest Side, you’ll find charming workers cottages, landscaped row houses, and simple brick two-flats. It’s ideal if you’re looking for something with a bit of historic charm; more than half of the housing stock was built before 1940. Both renters and buyers should be happy here—the neighborhood is split evenly between the two.
White Sox fans will love that Guaranteed Rate Field calls this neighborhood home. And it’s affordable to boot: The two-bedroom average rent was $1,200, and the median sale price was $312,900 in 2019, according to Zillow. Bridgeport is close to both Pilsen and Chinatown, which means you’ll never be too far from restaurants—hello, dim sum or tacos—and the Bridgeport Arts Center boasts a full roster of classes and events. It’s also posed to get even better: The proposed Paseo Trail, a path akin to the 606 that will run north of the neighborhood, is moving along, too.
The draw: A quiet neighborhood bordering the lush North Branch
Similar neighborhoods: Roscoe Village; Avondale
Don’t miss: Horner Park
Everything in this North Side neighborhood revolves around Lincoln Avenue: cozy Irish pubs and breweries, Hawthorne’s antique furniture, storefront theaters, and coffee shops.
Renters and buyers will both find lots of options—think mid-size terra-cotta-clad apartment buildings, rough-cut greystones, contemporary brick condos, and waterfront homes on the North Branch. Real estate is a bit more expensive, but the convenience and charm of the North Center is hard to beat.
What’s the average rent? For a two-bedroom, it was $1,700 at the end of 2019. This year, the median listing price of homes is $634,900, but, in reality, properties often sell for less; the median sale price in 2019 was $433,700, according to Zillow. Home-value forecasts say that prices in North Center, along with popular nearby ’hoods Roscoe Village and Lincoln Square, are expected to rise, so move in before the market gets hot.
Other perks include reliable public transit like a few Brown Line stations. Plus, Western Avenue is on track to get dedicated bus lanes this year. Don’t worry about being too far from the Lakefront Trail—North Center features lush riverside parks and the longest pedestrian bridge in Chicago, as well as 312 River Run, which connects Clark and California parks. What’s more, the surrounding nature and overgrown river’s edge make this area quiet and peaceful. That’s hard to come by in a city that seems to have an endless supply of construction cranes dotting the sky.
The draw: A lakefront neighborhood next to a verdant historic park
Similar neighborhoods: Kenwood; Woodlawn
Don’t miss: Rainbow Beach Park
The South Shore’s biggest draw is the South Shore Cultural Center, a landmarked Mediterranean Revival building—and host of the Obamas’ wedding reception—that was a former country club until the Park District claimed it.
The predominantly black neighborhood also features Theaster Gates’s vibrant community space, the Stony Island Arts Bank. Here, pop culture and history nerds peruse the Johnson Publishing Company’s archive, the University of Chicago’s architectural history glass slides, and Frankie Knuckles’s vinyl collection.
Residents reap the benefits of a lakefront neighborhood nestled just south of sprawling Jackson Park, which will be soon host the Obama Presidential Center (it was supposed to break ground in 2020). However, it’s just far enough away from the University of Chicago and the buzz of the Obama Center that home prices are still affordable; the median price of current listings is $100,000, while the median rent is $1,100.
History buffs will love that that this neighborhood got its start during the World’s Fair in 1893. The first homes constructed showcased new ideas like large front-yard setbacks and wide 50-foot lots. Today, two historic districts protect the stately homes in Jackson Park Highlands and the South Shore bungalows.
About 41 percent of commuters use public transit, a higher percentage than the city as a whole, so you’ll be among a crowd that prioritizes buses and rail over cars. Plus, advocates pushing for lower fares on Metra Electric—the line that runs through the neighborhood—made progress last year, which means transit could get even more affordable.
The draw: Square footage; affordability; lots of green space
Similar neighborhoods: Logan Square
Don’t miss: The swan pedal boats at Humboldt Park Lagoon
Wide, tree-lined streets, two-flats, and its status as the epicenter of Puerto Rican culture in Chicago make Humboldt Park a beloved West Side neighborhood. First, you’ll find plentiful recreational opportunities at the 606 Trail, the neighborhood’s 207-acre namesake park, and Garfield Park. Art is also everywhere—murals, mosaics, and painted doors color the streets. Many of the murals depict Puerto Rican history; keep an eye out for Cristian Roldán’s 2016 mural and Gamaliel Ramirez’s colorful Birds of Latin America, which he painted in 1980.
A homegrown art scene. A sprawling park with a lagoon and winding paths. Boulevards with plenty of foliage. What more could you want? Affordability and spacious apartments? It’s got that, too.
Many of the two-flat brick buildings and greystones were built before 1940, which means more square footage for potential homeowners looking to spread out. That perk extends to renters as well: You’ll find more two-bedrooms than in other parts of the city; they make up about 39 percent of the neighborhood’s housing. Even better? Average monthly rent for a two-bedroom is a steal at $1,350, and the bump in space is ideal, especially when new apartments and condos are getting smaller and smaller.
The draw: New parents flock to this idyllic neighborhood
Similar neighborhoods: Morgan Park
Don’t miss: The Original Rainbow Cone
Dreaming of a home with tons of space and a backyard? That’s what you’ll find in South Side Beverly. Unlike neighborhoods closer to the city center, Beverly started as a suburban development with expansive lots. The neighborhood’s Longwood Drive historic district offers a range of stunning Italianate, Carpenter Gothic, Queen Anne, and Prairie School houses—most built between 1890 and 1930.
Beverley has one of the highest rates of homeownership in Chicago—76 percent of people own their homes—so buyers looking to cultivate community will be in good company.
The neighborhood also looks downright irresistible thanks to its historic houses, huge yards, and idyllic scenes (there’s even a 133-year-old Irish castle). Even better is the current median listing price of $339,450. Affordability coupled with space means that parents with kids, this is your scene: More than 70 percent of residents are families. And you can feel secure in your investment: When sales dropped last year, folks were still buying in Beverly.
The draw: A lively entertainment district with lakeside apartments
Similar neighborhoods: Buena Park
Don’t miss: The Green Mill
For those who want solid transit options, crave easy access to the lakefront, and love apartment living, look no further than Uptown. A project to bring faster, more reliable service for downtown commuters on the Red and Purple lines finally got started last year and will wrap up in 2021.
Lakefront living is a priority for many Chicagoans, and there’s a lot to take advantage of on this stretch of Lake Michigan. Get outside at Montrose Beach by strolling to the tip of the harbor at the huge lakefront park, watch for the migration in the woodsy bird sanctuary, and join the many cyclists and runners on the Lakefront Trail.
Uptown is also a renter’s paradise, with abundant apartments including a swanky rehabbed building with midcentury modern inspiration and a tiki lounge. The majority of buildings in this ’hood are mid- to high-rise apartments with contemporary lobbies, doormen, and sweeping city views. The median rent is about $1,425, which is around $300 less than the median across Chicago.
If you want to buy, you’re looking at a median sale price of $271,500, and a majority of properties will be contemporary condos and co-ops. You may even find a cute Prairie School-style house here and there, but homebuyers looking for two-bedrooms with a balcony and shared courtyard will have more options.
Another reason to pick Uptown? It’s got a lively entertainment district (the Green Mill, Riviera Theater, Aragon Ballroom), and work could begin this summer on Uptown Theater’s long-awaited revival.
The draw: An architecture buff’s Prairie School paradise
Similar neighborhoods: Berwyn; Forest Park
Don’t miss: Frank Lloyd Wright’s home and studio
Oak Park is technically a suburb, but the neighborhood is just on the other side of city limits. The well-connected area is located 10 miles from the Loop, offering easy access downtown on the Green Line and I-290.
But the real reason Oak Park makes our list is due to the striking homes with midcentury—read: Frank Lloyd Wright—pedigrees. The architect made his home here, and there’s no better place to observe his evolution; the neighborhood is home to 25 Wright designs, making it the largest concentration of Prairie School architecture in America.
Architecture buffs will be smitten with more than 60 designated historic landmarks, seven buildings on the National Register, and three historic districts. And there’s no better time to buy: Oak Park median listing prices recently dipped down to $347,900. Those looking to score a deal should know this market favors homebuyers, with properties selling about 3.9 percent under asking, according to Redfin.