Chicago has a way of standing out. From its striking skyline and historic architecture to its lakefront views, neighborhood pride, and celebrated food scene, the city offers a mix of big-city energy and local character that makes it unlike anywhere else.
This Redfin article will uncover many compelling reasons why Chicago is a sought-after place to live. So whether you’re just curious about the city, a long-time local, or you’re a newcomer searching for a home in Chicago, here’s why so many people are proud to call the Windy City home.
1. Architecture and the skyline
Chicago’s reputation begins with its skyline. As Mersudin Velic of Urban Media Chicago notes, “The city is known worldwide for its architectural heritage, blending historic character with world-class design. From the classic terra-cotta facades of the Loop to the modern glass towers along the river, the city’s design history is visible at every street corner.”
Architects often cite Chicago as a place where design shapes civic life. Carol Ross Barney of Ross Barney Architects emphasizes, “Chicago is defined by a deep commitment to shared urban life.” Their work on the Chicago Riverwalk demonstrates how the city transforms infrastructure into a beloved civic space. This commitment to design extends from cultural destinations like the Searle Visitor Center at Lincoln Park Zoo to transit hubs like Morgan Station in the Fulton Market district.
2. The Chicago River
The Chicago River, once primarily an industrial waterway, has evolved into a public corridor where architecture and nature converge. The river provides a natural vantage point to appreciate the city’s dense collection of landmark buildings, from the ornate terra-cotta designs of the early twentieth century to the sleek glass towers defining the modern era. Walking along the riverwalk, residents and visitors interact with the water on a daily basis, enjoying dining, public art, and landscaped paths that connect major transit and cultural hubs. This waterway acts as both a functional transit spine and a leisure destination, reflecting the city’s ongoing commitment to reclaiming industrial space for the public good.
3. The neighborhoods
While the skyline attracts attention, Chicago’s neighborhoods are what Chicago locals value most. Pete Lauer of Strong Towns Chicago describes the city as “a place where a three-flat, a corner store, a taqueria, and an “L” stop sit on the same block.” Residents often rely on foot or bike travel for their daily needs, fostering a sense of community ownership.
Each neighborhood functions like its own downtown, offering its own hidden gems. Whether in Pilsen, Chinatown, or Andersonville, local shops are owned by neighbors, keeping money within the community. This structure provides a sense of responsibility for one’s specific block. As Lauer puts it, if asked, the thing most Chicagoans would take the most pride in about the city is their neighborhood.
Dolores Vlad from Luminous Blooms, a local florist company, shares her love for the area, suggesting, “When visiting Chicago, you must visit and stroll our quaint North Shore suburbs such as Downtown Highland Park. There you will find an ample number of women-owned boutique stores. Stop by That Little French Guy for great-tasting food. Another favorite is Town and Oak in Winnetka. Here you will find excellent tasting coffee and delicious menu items.”
Kpoene’ Kofi-Bruce from Ette the Wedding Tailor adds, “If you’re a food lover, Chicago is your paradise, with entire neighborhoods just waiting to help you on your culinary adventures. From Pilsen on the South Side (come for the fantastic and authentic Mexican food, stay for the art) to Argyle Street’s Little Vietnam strip on the North Side, Chicago has something for you, no matter the flavor you crave.”
4. Iconic landmarks and culture
The city is home to several landmarks that represent its scale and history. Cloud Gate, often called “the Bean,” sits at the center of Millennium Park and remains one of the most recognized public art installations in the world. Marina City and the Willis Tower further define the visual narrative of the city.
The city fosters an active community of artists who prioritize collaboration and mutual support. Local creators help keep the Chicago art scene alive and successful. For those seeking contemporary exhibitions, West Town serves as a central hub for modern galleries along Chicago Avenue. Collectors often frequent spaces like the Carl Hammer Gallery or 65GRAND Gallery in Humboldt Park to find distinct local work. Throughout the year, the public can engage with this community through consistent events, including the monthly openings at the Chicago Fine Art Salon, which highlight diverse artists.
5. Great music
Chicago’s musical heritage, from the birthplace of electric blues to thriving jazz and gospel scenes, continues to evolve and inspire. Iconic blues clubs in the city, like Buddy Guy’s Legends and Kingston Mines, feature legendary performers and offer an intimate blues experience.
Ronnie Frey, a local tour guide and photographer of Doorways of Chicago, encourages a visit to the Tortoise Supper Club, an elegant establishment with a nostalgic jazz-era ambiance. “On Friday and Saturday nights, they offer live jazz performances, creating an unforgettable experience. Don’t miss their unparalleled Beef Wellington – a true culinary masterpiece.”
Photographer Pedro Garcia of Albany Capture highlights that you cannot experience the soul of this city without catching a legendary concert at the Aragon Ballroom. This mix of grand scale and local culture makes Chicago stand out.
6. Local food staples
Culinary traditions in Chicago are tied to its history and hardworking demographic. These foods are as recognizable as the skyline:
- Deep-dish pizza: A layered, hearty staple known for its thick, buttery crust.
- Chicago-style hot dog: A poppy-seed bun topped with yellow mustard, neon green relish, onions, tomatoes, a pickle spear, sport peppers, and celery salt.
- Maxwell Street Polish: A savory, fried sausage sandwich rooted in the city’s street food history.
As Pedro Garcia notes, whether you are grabbing a late-night Maxwell Street polish or a deep-dish pizza from a local institution, the flavors here are as unforgettable as the skyline itself. Northern Fork, a Chicago-based catering company, agrees, “It’s no secret that Chicago is an incredible food city, with countless cuisines represented and iconic dishes like deep-dish pizza and the Chicago-style hotdog. Therefore, it comes as no surprise that catering companies can reflect the full scope of these incredible flavors.”
Lauren Caruso from Chicago Wick Stop, a local candle company adds, “We have some of the best food at restaurants like Apollonia in the South Loop serving up fresh house-made pasta and black truffle puff bread, to true Chicago tavern-style pizza at Tortorice’s on the west side,” Next, wrap it up with a drink like my favorite whiskey sour at one of the best bars in Humboldt Park since 1937, the California Clipper.
7. Urban parks
Chicago balances urban infrastructure with its public green spaces. Julia Bachrach, the author of The City in A Garden: A History of Chicago’s Parks, states, “Known as the ‘City in a Garden,’ Chicago has one of the nation’s most magnificent urban park systems. Highlights include over 2000 acres of lakefront parkland, gardens surrounding the Buckingham Fountain and other important monuments, two glass conservatories, and Prairie-style landscapes such as Humboldt and Columbus Parks, and the Alfred Caldwell Lily Pool in Lincoln Park. With over 550 parks and a vast network of forest preserves, Chicago truly lives up to its green motto.”
Frequently asked questions
What is the defining feature of Chicago?
Chicago is defined by its architectural history, its expansive lakefront, and its neighborhood-centric design. While the skyline is world-famous, the city’s strength lies in the distinct identity and community pride found in every neighborhood.
Is Chicago a walkable city?
Yes. The city’s structure, built around “L” stops and dense, mixed-use blocks, makes many areas highly walkable and accessible without a car. Chicago has a walk score of 77, making it the second most walkable city in the state. Residents often navigate their daily lives on foot or by bike.
How does Chicago’s weather impact its identity?
The city’s climate influences its architecture and lifestyle. Residents prioritize weather-resistant building materials and value indoor-outdoor transitions like the riverwalk and lakefront parks during the warmer months.
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