Why Visit Chicago? Key Facts About the City Where to Stay Top Attractions: Explore Chicago's Icons Exploring a City Where Culture Meets Competition: Museums and Sports Family-Friendly Experiences and Activities Dining in Chicago: Where to Eat Getting Around: Transportation in Chicago Travel and Budgeting Tips for Visitors Sample Chicago Itinerary Frequently Asked Questions About What to do in Chicago Nicknamed the “Windy City,” Chicago will sweep you off your feet in ways you don't see coming. Between its striking architecture and all the ways to explore it, from aboard a riverboat to walking “The Loop” on foot, it's truly a city built for wandering! If you're looking for ideas on what to do in Chicago, let the adventure begin. I've rounded up my favorite places, experiences, and can't-miss moments for every kind of traveler. Why Visit Chicago? Whatever you're up for, Chicago is game. Craving a simple change of scenery that lets you slow down? Long walks along the river and green spaces between landmarks let you breathe, while the glittering skyline reminds you you're still close to the excitement. Feeling adventurous and ready to pack your itinerary with activities? You're walking distance to photo-worthy attractions, and world-class museums to dip into between meals, bar-hopping and cafe coffee breaks. And what ties it all together is a certain hometown sensibility. Key Facts About the City Location: Chicago is a wildcard of the Midwest, sitting on the southwest shore of Lake Michigan Population: It's one of the largest cities in the U.S., home to roughly 2.7 million people. It's big enough to feel exciting and diverse, yet surprisingly personal once you start exploring its neighborhoods. Highly Walkable: The Chicago River cuts through the heart of downtown, creating a walkable hub of walking paths, restaurants, patios, and city views. Climate: Chicago experiences all four seasons, making it easy to tailor a trip to your preferred speed, from high-energy summers to slower, cozier cold months. An Unexpected Beach City: Chicago is home to 26 sandy beaches lining Lake Michigan, all free and open to the public during the summer, making it feel like a coastal city without the coastal crowds. Deep Dish Pizza Was Born Here: The city's all-star dish was first served in 1943. Ask two locals for pizza recommendations and you'll likely get two different answers, each delivered with confidence. Pro tip: Try them both, you won't be disappointed. Where to Stay Sports Illustrated Resorts Chicago 203 N Wabash Ave Chicago, IL 60601 | (312) 705-3900 In a city where sports are part of its ethos, staying somewhere that understands that energy just makes sense. Sports Illustrated Resorts Chicago puts you right in the middle of downtown, giving a home base that feels as dynamic as the city itself. It's right heart of the Loop, just steps from the Chicago River and a block off Michigan Avenue. From here, it's easy to walk to the Riverwalk, Millennium Park, and the Magnificent Mile, meaning your days can unfold naturally, without needing a car or a rigid schedule. FIND DATES Top Attractions: Explore Chicago's Icons Must-See Landmarks Millennium Park: If you do one classic Chicago photo moment, make it here. Millennium Park is open daily, and it's the easiest place to pack multiple icons into one stop. While you're there, make sure to visit Cloud Gate, AKA “The Bean.” The city's world-famous 110-ton polished stainless-steel sculpture is designed to reflect the skyline and clouds above, and is one of the most iconic photo ops you can take!Then stop by the Crown Fountain, an interactive public art installation designed by Jaume Plensa. It's a summer favorite for kids who want to splash and adults who want a great people-watching perch. The Chicago Riverwalk: The Chicago Riverwalk is one of the best ways to experience downtown. It runs 1.25 miles from Lake Michigan to Lake Street, with cafes, bars, boat tours, public art, and spots to simply sit and enjoy the view. Around golden hour, it transforms into a storybook setting that's perfect for photos, and you can feel the nightlife energy stir as daytime comes to a close. Willis Tower Skydeck: If your trip calls for an unforgettable, heart-racing moment, the Skydeck Chicago at Willis Tower lets you see Chicago from its most dramatic angle. You'll want to come here for the photo op, and the “I-can't-believe-I-did-that” story to text to the group chat. The main draw is The Ledge, a series of glass boxes that extend out from the building, letting you step beyond the tower and look straight down at the city below. Beyond the adrenaline rush, the Skydeck also serves up sweeping panoramic views that stretch for miles on a clear day, showcasing the city grid, Lake Michigan, and surrounding neighborhoods from above. Navy Pier: Navy Pier is great to have in your back pocket no matter how your day unfolds. You can arrive with a plan or none at all, and still leave feeling like you've experienced Chicago's waterfront atmosphere. Ride the Centennial Wheel, grab a casual bite or sweet treat, let kids explore the Chicago Children's Museum, or just take it easy and stroll the pier while watching boats come and go. Must-Do Activities The Chicago Architecture Center River Cruise: If you're going to choose one paid experience in Chicago, I'd suggest keeping this one at the top of your list. The Chicago Architecture Center River Cruise gives you a front-row seat to the city's skyline, paired with storytelling that brings the whole city to life. Operated aboard Chicago's First Lady Cruises, the tour is something everyone can enjoy. As the boat glides through the heart of downtown, trained docents guide you past iconic towers and lesser-known gems, explaining how Chicago became a global leader in architecture and design. It's informative without feeling academic, making it just as engaging for first-time visitors as it is for return trips. Even if history isn't usually your thing, the views alone make the experience worthwhile. Walk or Bike the Chicago Lakefront: Along the Lakefront Trail, you can walk, jog, or bike for miles with Lake Michigan stretching out beside you, often so vast it's easy to forget you're standing next to a lake. Beaches, green spaces, and scenic overlooks appear along the way, making it just as appealing for a leisurely stroll as it is for an active afternoon. I loved adding this small, but memorable activity throughout my trip, and it starts to feel like a familiar routine that makes the city feel that much more at home. Explore the Neighborhoods: The city's personality shines the most in its neighborhoods, so spend some time exploring them! Some of the most fun I've had in the city is wandering without a plan and ducking into a neighborhood hole-in-the-wall bar to grab a drink or enjoying a meal in a spot that feels authentically Chicago.Areas like Lincoln Park, Old Town, and Wicker Park are especially easy to explore and offer a mix of laid-back charm and local atmosphere. In Lincoln Park, tree-lined streets and nearby green spaces set the tone for relaxed afternoons. Old Town blends historic character with lively bars and classic comedy clubs. Wicker Park leans creative and eclectic, known for its indie shops, dive bars, and standout casual dining. Catch Art on THE MART: For another low-effort, high-reward evening plan, head toward the Riverwalk to experience Art on THE MART, one of Chicago's most impressive public art installations. After dark, the river-facing façade of THE MART transforms into a massive digital canvas, with large-scale video projections lighting up the building and reflecting across the water below. The experience feels immersive and cinematic, especially when viewed from the Riverwalk, where you can pause, linger, or simply stumble upon it during an evening walk. Best of all, Art on THE MART is completely free and typically runs nightly from April through December. Must-Visit Parks, Beaches, and Outdoor Spaces Lurie Garden in Millennium Park: Millennium Park is one of Chicago's most iconic gathering spaces, but tucked within it is Lurie Garden, a quieter, greener retreat that feels worlds away from the surrounding cityscape. Designed as a modern interpretation of a prairie landscape, you'll make your way through winding paths, layered plantings, and subtle seating areas that invite you to slow down and soak up your surroundings. Maggie Daley Park: Located just steps from Millennium Park, Maggie Daley Park is where Chicago's playful side really comes through. The park features attractions like a scenic ice skating ribbon, climbing walls, mini golf, and the expansive Play Garden, which makes it especially popular with families. Chicago's Beaches: Chicago's beaches are one of the city's most unexpected pleasures, stretching along Lake Michigan and offering a true summer escape right within the urban landscape. Oak Street Beach is the closest at about a mile away from your resort downtown, while North Avenue Beach draws a lively crowd with volleyball courts, bike rentals, and skyline views. Farther north, Montrose Beach offers a more laid-back atmosphere, with wide-open sand and space to spread out. Activities Available in Chicago Parks Chicago's parks offer plenty of ways to enjoy the city outdoors. Photo-worthy walks take you past iconic spots like Cloud Gate, the Riverwalk bridges, and Buckingham Fountain, while families can carve out some time to sunbathe by the beaches or nearby open spaces. For a more laid-back adventure, Millennium Park and the lakefront are perfect for picnics paired with skyline views. If you're craving movement, the Lakefront Trail treats you to miles of scenic paths ideal for biking or jogging with Lake Michigan as your backdrop. Exploring a City Where Culture Meets Competition: Museums and Sports Overview of Major Museums The Art Institute of Chicago: As one of the city's cornerstone cultural institutions, the Art Institute of Chicago pairs world-class collections with an unbeatable location just steps from Millennium Park, making it easy to work into a day downtown. It's home to iconic works from artists like Vincent van Gogh, Claude Monet, and Pablo Picasso, and a culture-rich way to spend the day. The Field Museum: The Field Museum is best known for its massive natural history collections, from towering dinosaur skeletons to immersive exhibits that explore cultures and ecosystems from around the world. All age groups can find something to enjoy here, with more than 30 exhibits on three floors. Step into the past by standing face-to-face with Sue, the famous T. rex. Then move through history and learn about mummification in one of the largest mummy collections in the country. And discover contemporary Native American culture through art, music, and dance. From there, experience the future with virtual reality to explore the ocean's ecosystems and encounter marine mammals. Chicago Cultural Center: When you want a moment of culture without committing to a ticket, make your way to the Chicago Cultural Center. Located right in the heart of downtown and with no admission fee, this landmark building feels special the moment you walk through the doors with grand Carrera marble staircases and soaring ceilings. It's a neoclassical marvel, with details like intricate mosaics made of glass, gold leaf, and mother-of-pearl. But the true showstopper is overhead. Look up to see the world's largest Tiffany glass dome made of 30,000 pieces of iridescent favrile glass. Beyond its grand architecture, the center is home to a dynamic exhibition program with historic and temporary art from around the world. There's a real focus on emerging and underrepresented artists who live and work in Chicago, which makes the experience feel connected to the city itself. Experience Chicago's Sport's Culture Wrigley Field: If you're visiting during baseball season, catching the Chicago Cubs at historic Wrigley Field is a classic experience. It's the National League's oldest ballpark, with a historic charm you instantly feel. The ivy-covered walls and neighborhood setting make it feel intimate and iconic all at once. Rate Field: On the South Side, the Chicago White Sox bring their own loyal following to Rate Field. The ballpark experience is modern and fan-friendly, with strong sightlines, classic stadium eats, and plenty of space to settle in and enjoy the game. United Center: Basketball and hockey fans can head to the United Center, home of the Chicago Bulls and Chicago Blackhawks. There's a larger-than-life energy here, with giant screens, roaring intros, and a crowd that celebrates its teams well. Soldier Field: Football season brings attention to the Chicago Bears, with fans filling both Soldier Field and sports bars across the city. The stadium is a spectacle, set along the lakefront with skyline views in the background that creates a dramatic setting. And if soccer is more your speed, tap into the hometown pride with the Chicago Fire FC. Family-Friendly Experiences and Activities Top Attractions for Children Chicago Children's Museum: Located right on Navy Pier, the Chicago Children's Museum is built around interactive, multi-sensory play-oriented exhibits that encourage kids aged 10 and under to learn by doing, not just watching. Little ones can climb and build in the Tot Spot, a space designed for toddlers and preschoolers. In the Waterways exhibit, kids can experiment with pumps, dams, and canals, while the Dinosaur Expedition gives children the freedom to explore fossils and dig for bones. It's a great break from museums that are more “look, don't touch.” Adler Planetarium: For families looking to add some cosmic wonder to their Chicago itinerary, the Adler Planetarium delivers big experiences that are fun and accessible for kids and adults. I learned that it was the first planetarium in the United States, and walked in not sure what to expect, but was completely blown away. What awaited was interactive exhibits, hands-on displays, and immersive sky shows that bring the universe to life in a way that doesn't feel like a traditional museum visit. You'll journey through the cosmos, where displays trace the evolution of the universe through time, and see the actual Gemini 12 spacecraft that once carried NASA astronauts.But one of the most memorable experiences happens just outside the main building. The Doane Observatory houses the largest public telescope in the Chicagoland area. On Wednesdays, you can peer through it and see planets, moons, stars, and distant celestial objects that are trillions of miles away. Shedd Aquarium: Before you even step inside, the building makes an impression with its grand neoclassical Beaux-Arts design standing as a historic landmark along the lakefront. Once inside, you can move from colorful coral reefs to icy polar habitats, and playful sea otters to massive ocean tanks that stop you in your tracks, with more than 32,000 animals. The exhibits are immersive without feeling overwhelming, and the peaceful flow of the space makes it simple to wander at your own pace. Lincoln Park Zoo: Spend the day at one of the most historic zoos in North America, and the best part is, it's completely free to enter. Tucked into Lincoln Park just north of downtown, you'll find beautifully landscaped grounds with habitats that house everything from big cats and gorillas to penguins and farm animals. Affordable Activities for Families Many of the activities mentioned earlier are also easy wins for families. Chicago makes it simple to have memorable days without overspending—between free icons like Millennium Park and the Chicago Cultural Center, scenic walks along the Riverwalk, and flexible, pay-as-you-go fun at Navy Pier and Maggie Daley Park. Dining in Chicago: Where to Eat Local Culinary Specialties to Try Chicago dining can be as casual or as celebratory as you want, and Chicago gives you plenty of range! I've included some recommendations below, but in case you have other plans, make sure you don't skip out on these local favorites at least once. Chicago-style pizza: Deep dish gets the headlines, but Chicago is also known for tavern-style and stuffed pizza. Chicago-style hot dog: If you want the “dragged through the garden” experience, Vienna Beef's classic Chicago-style lineup includes relish, sport peppers, mustard, and celery salt—plus you add fresh onion, tomato, and a pickle spear to go all the way. Italian beef: A downtown classic (especially for families and late lunches), and easy to find near River North. Popular Restaurants and Cafes Lou Malnati's: A go-to for Chicago deep dish pizza with a neighborhood fee. It's as authentic as you can get, thanks to the family recipe that's been perfected over five decades. Portillo's: The River North location pairs Italian beef, Chicago-style dogs, and hearty comfort food with a fun, retro vibe that works just as well for families as it does for a quick solo bite. Save room for dessert—the cake shake is practically a rite of passage and worth the hype. Mr. Beef: This sandwich staple on Chicago's West Side has been serving some of the city's most sought-after Italian beef sandwiches for decades. The star of the show is simple and unforgettable: thinly sliced, slow-roasted beef piled generously on a soft roll and dipped in savory jus, then dressed to your taste with sweet peppers or fiery giardiniera. Girl & the Goat: A staple of Chicago's West Loop dining scene, Girl & the Goat is known for bold, globally inspired flavors and a menu built for sharing. Chef Stephanie Izard's approach encourages you to order a few dishes for the table and try a little of everything, which makes the experience feel lively and communal. The Gage: It's a “Michigan Ave gastropub” vibe with rustic-refined comfort food that's excellent when you want a more upscale yet solid meal near Millennium Park. Best Spots for a Drink Cindy's Rooftop: Cindy's Rooftop gives you sweeping views of the city and the lake that somehow make even a casual drink feel like an occasion. I loved how it felt lively without being overwhelming as the kind of place where you can linger, talk, and watch the city move below you. Charis Listening Bar: Designed with rhythm and mood in mind, the space feels like stepping into a friend's stylish living room, complete with warm lighting, vinyl grooves, and an intimate atmosphere. The inventive cocktails are labelled by “genre” like juicy, citric, bitter, and funky so you can choose a pour that fits your taste as effortlessly as picking a favorite record. Bisous: For a classic martini, glass of French wine, or a signature drink mixed specifically to match the moment, this 1960s Parisian-inspired cocktail bar feels like a chic escape in the heart of Chicago and wraps you in cozy velvet booths with a moody atmosphere. Timothy O'Toole's Pub: This is the spot you pop into for “one drink” and end up staying awhile. It's lively without being overwhelming, packed with TVs for sports fans, and serves up hearty comfort food that hits the spot after a long day of sightseeing. Getting Around: Transportation in Chicago Recommendations for Navigating the City Chicago is one of those big cities that's surprisingly easy to navigate. I'd recommend walking to get around the Loop and nearby neighborhoods, but accessible public transportation is a great option for getting around town and spots like the sports arenas. Public Transport Overview The “L” Train: The city's “L” train system is efficient, affordable, and straightforward to use, making it a great option for getting around without a car. Buses: Buses run frequently throughout the city and are well-marked, with routes that cover major streets and popular areas. Rideshare Apps: Uber and Lyft are widely available and great when you want a more direct route or are heading out later in the evening. Travel and Budgeting Tips for Visitors Dress in layers. Chicago weather changes fast—especially near the lake. Book ahead. Popular attractions and rooftops fill up quickly. Wear good walking shoes. Many highlights are best explored on foot. Leave room to wander. Some of the best moments aren't on the itinerary. Use public transit. The “L” and buses make getting around easy and affordable. Mix in free attractions. Parks, public art, and river walks are standouts. Time meals strategically. Early or late dining makes busy spots easier. Sample Chicago Itinerary Day 1: Downtown Icons Morning: Millennium Park (Cloud Gate, Crown Fountain, Lurie Garden)Afternoon: Chicago Riverwalk + Architecture River CruiseEvening: Riverwalk drinks + Art on theMART Day 2: Museums & Views Morning: Art Institute of ChicagoAfternoon: Willis Tower Skydeck + lunch downtownEvening: Cindy's Rooftop or Timothy O'Toole's Pub Day 3: Lakefront & Local Flavor Morning: Walk or bike the Lakefront Trail (Oak Street or North Avenue Beach in summer)Afternoon: Navy Pier (Wheel, Children's Museum, casual bites)Evening: Explore Lincoln Park, Old Town, or Wicker Park; dinner at Girl & the Goat Optional Day 4: Family or Sports Day Morning: Museum Campus (Shedd Aquarium, Field Museum, or Adler Planetarium)Afternoon: Lakefront stroll or park timeEvening: Catch a sports game or enjoy a final Riverwalk walk Frequently Asked Questions About What to do in Chicago What is the #1 tourist attraction in Chicago? Millennium Park is often considered Chicago's top attraction. Home to Cloud Gate, aka “The Bean”, it's centrally located, completely free to visit, and an easy way to experience the city's art, architecture, and energy all at once. What is Chicago most famous for? Chicago is best known for its bold architecture, deep-dish pizza, passionate sports culture, blues and jazz roots, and its scenic lakefront along Lake Michigan. How many days do I need in Chicago? Three to four days is the sweet spot for your first visit. It gives you enough time to see the highlights, explore a few museums, and spend time in different neighborhoods without feeling rushed. Game On, Chicago Chicago meets you where you are and rises to the occasion, bringing its A-game to every time you visit. With its walkable downtown, vibrant neighborhoods, and mix of culture, food, and outdoor space, it's a city that's as approachable as it is exciting. Base yourself in the Loop, keep your plans flexible, and you'll find that some of the most memorable moments come from simply being there.
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