As a Chicago wedding photographer I get to see more of the city than most. I’m excited to share what I love about Chicago. Chicago is a city known for its delicious deep-dish pizza, beautiful architecture, and stunning lakeside views. Often called the “Windy City,” there are many reasons why locals love Chicago and choose to call it home. If you’re a local renting an apartment in West Loop or a tourist just visiting for the week, or planning to move here and you’re just wondering what locals love about living in Chicago, this is the article for you. Redfin reached out to locals, including us, to share our favorite reasons why we love Chicago. From the distinct neighborhoods to the vibrant arts and entertainment scene, Check out The Windy City Debunked – What Locals Love About Chicago to see what we had to say.
What makes Chicago great is the many neighborhoods in and around the city. Each neighborhood offers distinct landmarks, beautiful greenery, and a bustling atmosphere. Karen Shoufler, a local Chicago photographer shares, “my favorite thing about the city is that each neighborhood is so unique and offers up different aesthetics, unique food choices, and an interesting blend of people. I’m constantly finding and falling in love with different parts of the city and learning about the history of the neighborhood and its people.” Wicker Park Inn, a boutique bed and breakfast, adds, “Each neighborhood has a unique story narrated by architecture, stores, and food. There is a strong sense of community and pride in our city.”
With more than 200 neighborhoods to choose from, you’ll be sure to find something to do. “Each neighborhood has so many unique restaurants, shops, and activities to do. I could neighborhood hop every time I am in the city and have a totally different and fun experience,” says Mackenzie Maeder, a Chicago photographer and videographer.
Some notable neighborhoods to check out include Streeterville, which is great for young professionals and offers easy access to the lake and the Navy Pier, as well as Lake View which has excellent nightlife. There are even many hidden gems within each neighborhood to explore too. One that’s filled with history is Pickwick Place, a hidden coffee shop located in Chicago’s South Loop neighborhood. “I love Pickwick Place – a little half-alley hidden between State and Wabash on Jackson,” shares Adam Selzer of Mysterious Chicago. “It was named that in the 1800s because it looked like something out of Dickens’ The Pickwick Papers and the tiny building at the back was an English chophouse. Today’s it’s a lovely nook with a coffee shop where the chophouse was.”
Chicago experiences all four seasons. Winters are typically cold and consist of freezing temperatures, snow, and high winds, while summers are warm, wet, and humid. The fall and spring seasons bring a mix of cold and hot temperatures with plenty of sunny skies.
Hyde Bark Dog Walking & Pet Care + Hyde Bark Play Park boasts, “We love Chicago because we get to experience all the weather while out walking dogs. We like to take dogs out on perfect sunny day walks, and also see their joy playing in the snow, splashing in puddles, or chasing fallen leaves.”
Chicago is filled with iconic architecture throughout the city. Hillary Marzec of Inside Chicago Walking Tours shares that her favorite aspect of Chicago is the architecture. “I’m in love with Chicago’s architecture, and I especially like introducing locals to buildings they pass every day without ever peeking inside.” Some buildings that visitors and locals can pay a visit to include the Wrigley Building, Tribune Tower, TheMART, Marina City, and the Rookery Building.
Bozena Voytko also raves about “the stunning iron staircase in the Rookery Building that winds down from floor 12 to floor 2. As a wedding and real estate photographer, I’m constantly discovering new spots in Chicago and its suburbs that are worth seeing and contributing to the city’s uniqueness.”
While walking by foot or taking public transportation is an easy way of checking out Chicago’s architecture, one lesser-known option is taking an architectural boat tour. “We love taking a boat tour in the summer in Chicago because you can travel through the city and view the unique architecture. It’s the best way to view the city in 90 minutes,” shares Chicago Line, an architectural river cruise.
The Chicago River runs through the city via Lake Michigan, and flows south to the Calumet River system. There are many activities that you can do on the Chicago River including kayaking, dinner cruising, and fishing. “We love the river, its bustling life, and the beautiful buildings along its banks. Our favorite activity is taking an architectural tour on the river learning about the history of the buildings and meeting tourists from all over the world” shares Sam and Rev from What Yacht To Do. One fun Chicago tradition that happens every year is when the city dyes the river green to celebrate St. Patrick’s Day.
There are a number of amazing parks around Chicago. Some you need to check out include Millennial Park, Grant Park, and Lincoln Park. There are also a lot of less-trafficked parks like the Excelon observatory at The 606, Milton L Olive III Park, and Northerly Island. Joe U Photo shares that his favorite place to spend time in the city is the trail and the series of parks that run along the river starting north of Lawrence. “It’s quiet and usually not very crowded which makes it the perfect area to go on a run without being embarrassed by how slow I am at running.”
One most notable park is the Alfred Caldwell Lily Pool located at the Lincoln Park Conservancy which consists of long nature trails, a stunning pavilion, and a beautiful lily pool. “As a lifelong Chicagoan, I love Chicago’s multitude of free green spaces. My absolute favorite is the Alfred Caldwell Lily Pool, where you can kick back and take in the view and the wildlife,” boasts Carly Pastorelli of Snappy Paws.
When you think of Chicago, you probably think of Lake Michigan. Lake Michigan is one of the five Great Lakes of North America, and there are many activities that are sure to please any visitor. “You can go for a swim, relax on the beach, or bike down the beautiful lakefront trail — all with a spectacular skyline view. The sunrise over the water is not to be missed,” says Sarah Nader, Chicago wedding photographer.
“Lake Michigan is one of the cleanest and purest fresh-water lakes in the world. Sailing in Chicago offers the most amazing skyline that you can ever see. The only place you can see it is out on a boat on the water,” adds SailTime, a boat rental company.
There is something for everyone on and around Lake Michigan with many parks, sand dunes, and bike and walking trails to explore. There are also many hidden gems along Lake Michigan reveals Shalimar B Photography. “I love everything that Chicago has to offer, but if I was asked to choose a few things, I’d have to say the lakefront and all of the amazing parks in the city. Not only do I love to spend time with my own family and friends in these sometimes hidden gems, but I really love to photograph the families of Chicago in these types of places – the sandy beaches, or a lush garden park with an urban backdrop.”
During the summer, there are many outdoor activities to take advantage of in Chicago. Some activities that locals enjoy include kayaking down the Chicago River, biking by the water on the Lakefront Trail, taking a dip in Lake Michigan, relaxing on Margaret T. Burroughs Beach, or going on a nature walk. When it comes to outdoor activities, Carefree Boats shares, “When those steamy 90-degree days in Chicago start occurring more frequently, our favorite thing to do is take a boat out and anchor in the ‘playpen’ next to Navy Pier. The breathtakingly expansive Chicago skyline, cold drinks, fellow boaters, and even a boat that goes around with the infamous red cooler tamales make this spot one of a kind. If you stay late enough on Wednesdays and Saturdays, you can catch the fireworks display over navy pier with a lit-up city as the backdrop.”
Chicago is known for its culture filled with a rich music scene, chic art, diverse languages, and a bustling sports scene. Not to mention the theater and entertainment scene with over 200 shows from different production companies that are put on each week.
“I love Chicago for the same reasons I moved here 30 years ago,” boasts Merry Puppins Chicago, a local dog and cat sitting service. “The vibrancy of collective cultures and neighbors from all over the world, the big beautiful lake next to the city, riding along the bike path in the summer, wonderful local parks and green space, multiple global restaurants at our fingertips, great public transportation and all of the various neighborhoods, with their unique personalities.”
While other cities like Los Angeles, CA, and New York, NY are known for their food scene, Chicago’s food scene is a little more underrated. The city loves to put spins on classic food dishes and is home to a handful of delicious “cheap eats” spots. Some notable restaurants to check out include Smoque BBQ for some delicious St. Louis style baby back ribs and Pequod’s Pizza for some deep dish pizza.
“Our team’s favorite thing about Chicago is that it’s home to an underrated diverse restaurant and foodie scene. While deep-dish will always be a city staple, thousands of restaurants around the city bring unique global flavors to life with renowned culinary talent that shouldn’t be slept on. Some of our favorites include Kasama’s Filipino fine-dining experience and Funkenhausen, a modern beer hall mash-up of Southern and Bavarian flavors,” boasts Notch.
“While Chicago is known to blues fans all over the globe, music fans flock to our city to hear everything from classical to rock, jazz, gospel, folk, country, soul, R&B, hip hop, and rap. Not to mention world and ethnic music of all types. Our many music festivals and venues attract millions of music lovers who come here for everything from Lollapalooza to the Chicago Symphony,” stated Linda Cain, Editor and Founder of Chicago Blues Guide.
It’s true, Chicago has a vibrant and lively music scene. The birthplace of music genres like Chicago style-blues, modern gospel, and house, there are a ton of venues you can catch a live music concert, including Subterranean in Wicker Park, Lincoln Hall in Lincoln Park, and Simone’s in Pilsen. Every year, Chicago also hosts premier music festivals like Lollapalooza and Windy City Smokeout.
Chicago offers some of the best in musical theater putting on shows such as Dear Evan Hansen, Wicked, The Lion King, Anastasia, and Hamilton. These shows live in iconic theaters like the Cadillac Palace Theater, CIBC Theater, Broadway Playhouse, and James M. Nederlander Theater. “Chicago is a theatre town through and through. From Broadway hits to storefront theatre, there’s always something new to see,” chimes Chicago Youth Shakespeare.
Chicago first became a city in 1837 when its population hit 4,000 residents. Today, Chicago is the 3rd largest city in the United States with a population of around 2.6 million. The city has a long history from the Great Chicago Fire, which burned roughly 3.3 square miles of the city, to the resurrection of the first skyscraper. “The city has such a rich history you can’t help getting lost in its streets as if they were your own personal adventure map. From Michigan Ave., which houses some of America’s most iconic landmarks, down Damen Blvd., where people gather alongside musicians waiting for their next song inspiration, Chicago is a family-friendly city with something to offer everyone,” says Emily Cummings of Ten Little Blue Birds.
Overall, what’s not to love bout Chicago? Chicago has “a dynamic history, sports, food, architecture, arts, shopping, music, bird watching, comedy, beaches and so much more are right at your fingertips,” shares Chicago Crime Tours. “From listening to the Chicago Symphony Orchestra at Pritzker Pavilion and seeing the most recent exhibit at the Art Institute to riding your bike around the Lakeshore path or 606 and grabbing a drink at your favorite neighborhood bar’s beer garden, there is something for everyone in Chicago,” adds Ed & Aileen Photography
All-in-all, what locals love most about Chicago is the pride they have for their city. When the city has a diverse food scene, beautiful neighborhoods, stellar attractions, vibrant nightlife, and a bustling arts and entertainment scene, it’s hard not to hold a little Chicago pride in your heart.
“Chicago pride is also something out of this world. It’s a culture here and we Chicagoans love our city. Others may see Chicago through news headlines but we that live here know this is a one-of-a-kind place with a lot of beauty to offer. We wear our city with pride and it’s a whole vibe,” raves Rocio Pagoada Photography.