Long before European settlers arrived, the area now known as Chicago was inhabited by Native American tribes, including the Potawatomi, Miami, and Illinois. These tribes used the area as a meeting and trading place due to its strategic location at the confluence of Lake Michigan and the Chicago River. The first European to explore the area was French explorer Louis Jolliet and Jesuit missionary Jacques Marquette in 1673. Jean Baptiste Point du Sable, a man of African and French descent, is considered the first non-Native permanent settler in Chicago, establishing a trading post in the late 18th century.

In 1803, the U.S. government built Fort Dearborn to establish a military presence in the area. The fort played a significant role in early Chicago's development but was destroyed during the War of 1812 and later rebuilt. Chicago was officially incorporated as a town in 1833 and became a city in 1837. The city's rapid expansion was driven by its strategic location, which made it a critical transportation hub.

The construction of the Illinois and Michigan Canal in 1848 connected the Great Lakes to the Mississippi River, boosting Chicago's role as a transportation hub. The expansion of railroads further cemented Chicago's status as a key transit point for goods and people. Chicago experienced rapid population growth in the 19th century, attracting immigrants from Europe and other parts of the United States. The city's ethnic diversity became a defining characteristic. In 1871, the Great Chicago Fire devastated much of the city, destroying a large portion of its buildings and infrastructure. Despite the destruction, Chicago quickly rebuilt, with new architectural innovations and city planning that reshaped its skyline.

In 1893, Chicago hosted the World's Columbian Exposition, also known as the Chicago World's Fair, to commemorate the 400th anniversary of Columbus's voyage to America. The fair highlighted Chicago's emergence as a major city and showcased its architectural achievements. Chicago became a center for architectural innovation, with architects like Louis Sullivan and the firm of Burnham & Root pioneering the development of skyscrapers. The city played a significant role in the birth of modern architecture.

In the early 20th century, Chicago experienced significant social and political changes, including the growth of organized labor and the influence of political machines like the Democratic Party's Cook County Machine. During the Prohibition era, Chicago became notorious for its organized crime, with figures like Al Capone gaining prominence. The city's gangsters and speakeasies became part of its history and culture. Chicago played a significant role in the Civil Rights Movement and other social movements in the mid-20th century. The city was a center for civil rights activism and saw significant racial and political tensions.

In the late 20th century, Chicago experienced a cultural revival, with the construction of modern architectural landmarks like the Willis Tower (formerly Sears Tower) and the development of Millennium Park. Chicago's economy diversified, with a focus on finance, technology, healthcare, and other industries. The city became a major hub for innovation and business. Today, Chicago is a major tourist destination, known for its rich history, vibrant cultural scene, iconic architecture, and diverse neighborhoods. The city's history is preserved in museums, historic sites, and cultural institutions.

Set against the dramatic backdrop of Lake Michigan, Chicago is a city that pulses with creative energy, architectural innovation, and cultural pride. It’s a city shaped by immigrants, artists, architects, and activists—a place where jazz was refined, skyscrapers were born, and theatre found its voice in intimate stages and bold performances. Whether you're here for a weekend or an extended stay, Chicago’s cultural offerings are both world-class and uniquely local.

No visit to Chicago is complete without a stop at the Art Institute of Chicago. This world-renowned museum, situated in Grant Park, is home to one of the most impressive and comprehensive art collections in the United States. Step inside and you’ll encounter masterpieces by Monet, van Gogh, Picasso, and Hopper. The museum’s Impressionist and Post-Impressionist collection is especially noteworthy, and its modern wing—designed by architect Renzo Piano—is a beautiful space to explore contemporary works. Travelers with an interest in American art should seek out Grant Wood’s American Gothic and Georgia O’Keeffe’s landscapes, while fans of pop culture will enjoy seeing the iconic painting A Sunday on La Grande Jatte by Georges Seurat, famously featured in Ferris Bueller’s Day Off.

Right outside the Art Institute is Millennium Park, a cultural destination in its own right. This downtown green space is famous for Cloud Gate (better known as “The Bean”), the reflective sculpture by Anish Kapoor that has become a symbol of modern Chicago. Equally compelling is Crown Fountain, designed by Spanish artist Jaume Plensa, which features video projections of Chicago residents and interactive water displays. Millennium Park also hosts free concerts, theater performances, and festivals at the Jay Pritzker Pavilion, designed by Frank Gehry. Whether you attend a summer symphony under the stars or simply stroll through the park’s gardens and installations, it’s a vibrant cultural hub in the heart of the city.

Chicago is often called the birthplace of the modern skyscraper, and its skyline is a living museum of architectural innovation. To understand the city’s design legacy, visit the Chicago Architecture Center, where exhibitions explore the evolution of Chicago’s buildings and their global influence. For an unforgettable experience, take a Chicago Architecture River Cruise. These guided boat tours offer a unique perspective on the city’s skyline and its architectural heritage, from the Tribune Tower’s neo-Gothic elegance to the sleek minimalism of Mies van der Rohe’s buildings. It’s one of the best ways to see the city and learn about its story through the lens of design.

Chicago’s theatre scene is among the most vibrant in the U.S., rivaling Broadway in both talent and diversity. The Steppenwolf Theatre Company in Lincoln Park has launched countless careers and presents powerful contemporary works. Just down the road, The Second City, the legendary comedy theater, is where stars like Tina Fey, Stephen Colbert, and Bill Murray got their start. The Goodman Theatre, Chicago Shakespeare Theater, and Lookingglass Theatre (housed inside the historic Water Tower Water Works) each offer innovative productions year-round. For travelers looking to experience live performance, these theaters showcase Chicago’s creative spirit and commitment to storytelling.

Beyond the Art Institute, Chicago is home to several other exceptional museums. The Field Museum of Natural History invites visitors to meet Sue, the world’s most complete Tyrannosaurus rex skeleton, and explore exhibits on ancient cultures, biodiversity, and geology. Nearby, the Adler Planetarium and Shedd Aquarium offer interactive, family-friendly experiences right on the lakefront. The DuSable Black History Museum and Education Center in Washington Park celebrates the history, culture, and achievements of African Americans, with exhibits ranging from civil rights to arts and politics. Named after Chicago’s first non-Indigenous settler, Jean Baptiste Point du Sable, this museum is one of the nation’s oldest institutions dedicated to Black history. In the Pilsen neighborhood, the National Museum of Mexican Art offers a vibrant, community-driven look at Mexican culture and contributions to American life. Its exhibitions, many bilingual, cover everything from pre-Columbian traditions to contemporary Chicano art.

Chicago has long been a musical powerhouse. The city played a central role in the development of blues and jazz, with legends like Muddy Waters, Howlin’ Wolf, and Louis Armstrong performing in smoky clubs along the South Side and West Loop. Today, venues like Buddy Guy’s Legends, Green Mill Cocktail Lounge, and Kingston Mines keep that heritage alive with nightly performances. For lovers of classical music, the Chicago Symphony Orchestra, based at Symphony Center, is one of the “Big Five” American orchestras and regularly draws top conductors and soloists from around the world. The Lyric Opera of Chicago, housed in the historic Civic Opera House, offers productions that range from grand classics to bold contemporary works.

Chicago has long inspired writers with its grit, grandeur, and complexity. It’s the city of Gwendolyn Brooks, Saul Bellow, Studs Terkel, Sandra Cisneros, and Nelson Algren—each of whom captured different facets of Chicago life. Today, literary fans can visit landmarks like the Newberry Library, an independent research institution with fascinating exhibits on books, maps, and manuscripts. Independent bookstores like The Seminary Co-op, Women & Children First, and Unabridged Bookstore are beloved by locals and offer great browsing, author events, and a true sense of Chicago’s intellectual character.

Chicago’s culture is deeply rooted in its neighborhoods. In Hyde Park, you’ll find the Smart Museum of Art and the DuSable Museum, along with the University of Chicago’s Gothic architecture and progressive academic legacy. In Wicker Park and Logan Square, vibrant murals, coffee shops, and pop-up galleries reflect the creative energy of a new generation. The city’s public art is also worth noting: from the Picasso in Daley Plaza to Calder’s flamingo sculpture in the Loop, art is integrated into everyday life. Even train stations and underpasses are canvases for mosaics and murals, many of which speak to Chicago’s social movements and multicultural identity.

To travel to Chicago is to immerse yourself in a living, breathing culture that’s proud, diverse, and endlessly evolving. From world-class institutions to neighborhood gems, the city’s cultural life reflects its people: bold, creative, and deeply engaged. Whether you’re wandering through a museum, swaying to live jazz, laughing at an improv show, or admiring a mural in a quiet alley, Chicago invites you not just to see it—but to feel it. Come for the skyline, stay for the soul. This is Chicago at its most inspiring.

Chicago might be known for its iconic skyline and deep-dish pizza, but it’s also a surprisingly green and wellness-forward destination. From scenic lakefront trails to historic parks and eco-conscious neighborhoods, the Windy City offers a fresh perspective on urban travel—one that encourages balance, connection with nature, and a smaller environmental footprint.

At the heart of Chicago’s green offerings is its remarkable Lakefront Trail, an 18-mile path that stretches from Edgewater in the north to South Shore in the south. Whether you’re walking, biking, or running, the trail provides uninterrupted access to Lake Michigan, with views of beaches, harbors, and downtown’s striking architecture. It’s one of the best ways to explore the city sustainably and stay active while taking in the sights. 

For a slower pace, Millennium Park and neighboring Grant Park offer serene oases in the heart of downtown. Stroll through gardens, reflect by the Crown Fountain, or attend a free yoga class on the Great Lawn during summer months. Further north, Lincoln Park provides a nature retreat with walking paths, a lily pond, and even a free zoo dedicated to conservation education. And if you’re looking for something more off the beaten path, Garfield Park Conservatory on the West Side houses lush indoor gardens and seasonal wellness events in a breathtaking glass structure.

Wellness in Chicago extends to the culinary scene, with a growing number of restaurants and cafes emphasizing plant-based menus, local ingredients, and zero-waste principles. Spots like Uncommon Ground (one of the first certified organic rooftop farms in the U.S.) and Handlebar in Wicker Park offer delicious, sustainable fare in laid-back, community-focused settings. For travelers who want to dive deeper, farmers markets—such as the long-running Green City Market—connect visitors with local growers and sustainable producers.

Getting around sustainably is easy in Chicago thanks to an extensive public transportation system, abundant bike lanes, and bike-share options like Divvy, which has stations across the city. Electric buses and increasing EV infrastructure also make it possible to reduce your carbon footprint while exploring further afield.

Wellness seekers will find no shortage of experiences to support mind-body health. The city boasts a thriving yoga and fitness scene, with drop-in classes available at studios like Yoga Now and Zen Yoga Garage, as well as waterfront pop-up sessions during warmer months. For spa lovers, there are urban sanctuaries like AIRE Ancient Baths, located in a restored River West factory, where visitors can unwind with hydrotherapy and massages.

In Chicago, wellness and sustainability aren’t afterthoughts—they’re woven into the city’s rhythm. From leafy parks to eco-conscious eateries and energizing outdoor spaces, the Windy City proves that big-city travel can still feel balanced, intentional, and rooted in nature. Whether you’re visiting for a weekend or just passing through, Chicago invites you to slow down, breathe deep, and reconnect—with the city, and with yourself.

Chicago is a city that eats well and eats boldly. With its rich immigrant heritage, diverse neighborhoods, and a fearless approach to flavor, it has earned a place as one of America’s great culinary capitals. From classic comfort food to boundary-pushing fine dining, street eats to award-winning global cuisine, culinary travel in Chicago is an experience of contrasts and discovery—one that reflects the city’s deep roots and dynamic energy. 

Let’s start with the essentials. No food journey through Chicago is complete without trying its signature dishes. The Chicago-style hot dog is a work of art and attitude: an all-beef frankfurter “dragged through the garden” with yellow mustard, relish, onions, tomato wedges, a pickle spear, sport peppers, and a dash of celery salt—all on a poppy seed bun. Notably, ketchup is never invited. Equally famous is deep-dish pizza, a dish that defies expectations. With its buttery crust, thick layers of cheese, chunky tomato sauce, and any number of hearty toppings, it’s less a pizza and more a full meal in a slice. Head to institutions like Lou Malnati’s, Giordano’s, or Pequod’s to sample this iconic dish in all its indulgent glory. But Chicago doesn’t stop at these classics. The Italian beef sandwich, dipped in au jus and topped with spicy giardiniera, is another must-try, particularly at local legends like Al’s Beef or Johnnie’s Beef in Elmwood Park. For something quick and deeply satisfying, don’t overlook the city’s many tamale carts, Polish sausage joints, and maxwell-style burgers—testaments to Chicago’s working-class roots and rich multicultural traditions.

Chicago’s neighborhoods tell their stories through food. In Pilsen, vibrant murals and Mexican heritage meet in taquerías and bakeries that offer everything from al pastor tacos to pan dulce. Nearby, Little Italy serves up old-school red sauce comfort, while Greektown plates moussaka, grilled octopus, and saganaki with a fiery “opa!” On the North Side, Devon Avenue is a destination for South Asian cuisine. Wander its storefronts to find samosas, biryani, and sweets like gulab jamun, or dine in restaurants that serve traditional Pakistani and Indian dishes with unmatched authenticity. Over in Argyle Street, a pocket of Uptown brims with Vietnamese, Thai, and Chinese eateries offering pho, banh mi, and dim sum. In Chinatown, just south of downtown, you’ll find a blend of traditional and modern dining experiences—from barbecue duck hanging in windows to sleek, contemporary spots serving Sichuan and Shanghai specialties. And in Andersonville, Swedish roots are honored through cozy cafes, while newer arrivals have added Middle Eastern, Korean, and Ethiopian flavors to the mix.

While its street food and comfort classics are a huge draw, Chicago also shines at the highest levels of cuisine. The city boasts a number of Michelin-starred restaurants, including Alinea, frequently ranked among the best in the world. Here, chef Grant Achatz serves up a mind-bending, multi-sensory experience that’s part theater, part science, and entirely unforgettable. Other acclaimed fine dining spots include Smyth, Oriole, and Elske, where seasonal, locally sourced ingredients take center stage in refined, creative menus. These restaurants highlight Chicago’s reputation as a center for innovation and culinary artistry. But you don’t need to go haute to eat memorably in this city. Chicago’s dining scene is full of chef-driven neighborhood restaurants that deliver excellence without the formality. Places like Parachute in Avondale (modern Korean-American), Mi Tocaya Antojería in Logan Square (bold Mexican flavors), and Virtue in Hyde Park (Southern cuisine with a fine-dining twist) offer inspired menus and warm, welcoming service.

Dessert lovers are in for a treat in Chicago. Beyond its excellent doughnuts (check out Do-Rite Donuts or Stan’s) and flaky, buttery croissants at bakeries like Floriole, the city also has a love affair with frozen indulgence. In summer, lines form at institutions like Original Rainbow Cone and Margie’s Candies, where vintage charm meets towering sundaes. For something sophisticated, try Bombon Café for Mexican pastries and tres leches cake, or Bittersweet Pastry Shop for European-inspired treats. And don’t forget to sample the beloved Chicago invention, Garrett Popcorn, especially the “Chicago Mix” of caramel and cheddar—a surprisingly addictive combo.

Chicago is a craft beer lover’s paradise, home to one of the most dynamic brewing scenes in the country. From the hop-forward innovations at Revolution Brewing in Logan Square to the experimental small-batch creations at Off Color and Half Acre, the city offers something for every palate. Many breweries double as taprooms and community hubs, where visitors can sample IPAs, barrel-aged stouts, sours, and lagers brewed just steps away. Neighborhoods like Pilsen, West Loop, and Ravenswood’s “Malt Row” are dotted with welcoming brewpubs and beer gardens, often paired with food trucks or pop-up kitchens. Exploring Chicago through its craft beer is a flavorful way to tap into its local spirit.

Travelers looking to connect more deeply with the city’s food culture should explore its many farmers markets, cooking classes, and food tours. Green City Market in Lincoln Park is a hub for local, sustainable produce and artisanal goods, while food tours through Tastebud Tours or Chicago Food Planet take you behind the scenes in the Loop, River North, and beyond. Sustainability is also a growing focus in Chicago’s culinary world. Restaurants like Uncommon Ground, which features the nation’s first certified organic rooftop farm, and Cellar Door Provisions, known for its small seasonal menu and zero-waste ethos, are at the forefront of conscious dining. Whether it’s reducing waste, sourcing locally, or building community through food, these eateries reflect Chicago’s evolving values.

Culinary travel in Chicago is about understanding the city’s neighborhoods, people, and history through flavor. It’s about recognizing the immigrant families who brought their traditions here, and the new generation of chefs shaping the city’s future. It’s about trying something unexpected, savoring something familiar, and enjoying every bite along the way. 

Chicago’s music scene is a living, breathing part of the city’s soul. With a rich legacy rooted in the migration of blues artists from the Mississippi Delta, and a vibrant present that spans from grand opera to neighborhood jazz clubs, Chicago remains one of the most important and diverse music cities in the world. Whether you're a fan of gritty guitar solos, sweeping symphonies, or soaring arias, Chicago offers unforgettable experiences for every listener.

At the heart of Chicago’s musical identity is the Chicago blues, a genre born in the 20th century when African American musicians from the South settled on the city’s South and West Sides. Amplifying the acoustic Delta blues with electric guitars, harmonicas, and raw vocals, artists like Muddy Waters, Howlin’ Wolf, Willie Dixon, and Buddy Guy transformed the sound of American music. Their influence can still be felt today in clubs like Buddy Guy’s Legends, a cornerstone venue where the blues legend himself occasionally performs, and in Kingston Mines, a late-night blues institution that hosts live music on two stages every night. If you're interested in the story behind the sound, a visit to the Chicago Blues Museum (coming soon) or a walk through Maxwell Street, the historic home of street blues performance, offers a powerful glimpse into the city’s cultural roots.

But Chicago isn’t all grit and guitar—it also boasts one of the finest classical music and opera scenes in the country. The Chicago Symphony Orchestra (CSO), based at the majestic Symphony Center on Michigan Avenue, is renowned worldwide for its artistry and excellence. Founded in 1891, the CSO continues to attract top talent and guest conductors, performing both classical masterworks and contemporary compositions in a stunning acoustic setting. Just a short distance away, the Lyric Opera of Chicago stages world-class productions in the historic Civic Opera House, a grand Art Deco building affectionately known as “Insull’s Folly.” The Lyric’s season includes beloved classics by Verdi, Mozart, and Puccini, alongside bold modern works and new commissions. It’s a must-visit for opera lovers or anyone curious to experience the emotional power of live performance on a grand scale.

Chicago’s musical richness doesn’t stop there. Free concerts in Millennium Park, performances by the Chicago Sinfonietta, neighborhood jazz clubs, gospel brunches, indie rock venues, and Latin music festivals all contribute to the city’s deep and inclusive soundscape. Music is part of the everyday rhythm of life. Whether you’re catching a blues set in a dimly lit club, dressing up for the opera, or listening to symphonic strings echo through Orchestra Hall, music in Chicago is history, passion, and identity wrapped in melody.

Chicago is a shopper’s paradise. Whether you're hunting for high fashion, vintage finds, local artisan goods, or global brands, the Windy City’s retail scene is as diverse and dynamic as its neighborhoods. From glittering flagship stores to indie boutiques, here are the best places to shop in Chicago. 

Start your retail journey on the Magnificent Mile, the iconic stretch of Michigan Avenue that runs from the Chicago River to Oak Street. This bustling boulevard is home to over 400 stores, including department store staples like Nordstrom and Bloomingdale’s, along with luxury brands such as Burberry, Gucci, and Tiffany & Co. The area is also home to the historic Water Tower Place, a vertical shopping mall packed with both familiar retailers and local gems. 

Just a few blocks north, Oak Street is Chicago’s answer to Fifth Avenue. This leafy, upscale district features designer boutiques and couture houses like Chanel, Prada, and Hermès tucked into elegant historic townhouses. It’s the go-to spot for luxury shoppers looking for exclusivity and personal service.

For those in search of something more eclectic and artsy, Wicker Park and Bucktown offer an entirely different vibe. These creative neighborhoods are filled with indie boutiques, vintage stores, record shops, and bookstores. Explore Una Mae’s, Myopic Books, or Reckless Records, and pop into Shangri-La Vintage or Mildblend Supply Co. for fashion with flair. The area also features local designers and pop-up shops that reflect the city’s youthful, trend-forward energy.

Andersonville, a neighborhood on the North Side, is beloved for its blend of Swedish heritage and vibrant LGBTQ+ community. Clark Street is lined with charming storefronts offering everything from handmade candles and home goods to ethically sourced fashion and used books. Don’t miss Women & Children First, one of the nation’s oldest feminist bookstores, or Foursided, a favorite for art, cards, and gifts.

If your tastes run more toward modern and curated, Fulton Market and the West Loop are home to stylish concept shops and home décor stores. Randolph Street Market, when in season, is a treasure trove for antiques, vintage clothes, and unique finds from local artisans. It’s perfect for travelers who want to shop sustainably while picking up something truly one-of-a-kind.

For a more relaxed, family-friendly atmosphere, head to Lincoln Square or Southport Corridor, where small businesses and neighborhood charm take center stage. These areas are great for boutique shopping, kids’ stores, and artisanal bakeries you’ll want to linger in.

Whether you’re splurging on designer labels, supporting local makers, or browsing for souvenirs, Chicago delivers a retail experience as multifaceted as the city itself.

African American Heritage Tour

Immerse yourself in Chicago’s rich and dynamic African American heritage during this half-day tour. Highlights include an interior visit to an African American museum, a stop at the birthplace of gospel music in Bronzeville, and a look at the Obama family home in Hyde Park, as well as Jennifer Hudson's childhood home.

Chicago Architecture River Cruise

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you'll cover multiple branches of the Chicago River and will learn insider facts and stories you'd otherwise miss.

Chicago Pizza Tour

Enjoy Chicago’s only bus guided neighborhood pizza tour. Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the best pizza. Your local guide will teach you the science behind ingredient selection and baking as you sample slices from historic pizzerias. In just a few hours, you’ll leave stuffed, and with an understanding of why pizza is such an important part of Chicago’s culture.

Chicago Walking Food Tour

Explore Chicago's buzzing food scene—and see some of its best-known landmarks on the way—on this two-in-one walking tour. With just your guide and small group for company (and the option to upgrade for a private experience), you'll stroll around the vibrant Loop area, spotting highlights from the Willis Tower to the Rookery building. As you go, indulge in classic Chicago foods, from deep-dish pizza to the world-famous dipped Italian beef sandwiches.

Chicago Walking Tour

Get an insider's introduction to Chicago's most celebrated buildings during this architecture-focused walking tour of Michigan Avenue, State Street, and the vibrant Loop area. Revisit the heyday of the skyscraper and visit stunning, art deco-era interiors, from the Palmer House Hotel to the Chicago Cultural Center. Admission to the Chicago Architecture Center is included, accompanied by an introduction from the docent.

Lake Michigan Sunset Cruise

Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel (with an enclosed and climate-controlled lounge) in the heart of the Magnificent Mile, and cruise along the Chicago River. Then, see the skyline from a distance, and watch the skyscrapers light up, as you continue to Lake Michigan for a sunset viewing.

Street Art Tour of Chicago

Discover a side of the Windy City that many visitors overlook—and immerse yourself in its vibrant street art scene—on this urban walking tour. With your art-expert guide in the lead, you can focus on soaking up the city's ambiance, and spotting artworks and murals you may not have discovered on your own. As you go, listen to in-depth commentary about the artists and artworks, and explore some of the city's hippest neighborhoods.