Chicago, the Windy City, is a world-class destination renowned for its stunning architecture, vibrant cultural scene, and beautiful lakefront. From iconic skyscrapers to deep-dish pizza, this Midwestern metropolis offers unforgettable experiences for every type of traveler. Discover the best things to do in Chicago with this comprehensive travel guide.
Take an Architecture River Cruise
The Chicago Architecture River Cruise is consistently rated as one of the city's top attractions. Glide along the Chicago River while expert docents narrate the history and design of over 50 iconic buildings. You'll see masterpieces from architects like Frank Lloyd Wright, Ludwig Mies van der Rohe, and contemporary designers.
The 90-minute tour operates year-round, offering unique perspectives during different seasons. Spring and fall provide comfortable temperatures, while winter cruises showcase the city's holiday lights. Book in advance, especially during peak summer months.
Top Architecture Tours:
- • Chicago Architecture Foundation River Cruise
- • Shoreline Architecture Cruise
- • Wendella Boats Architecture Tour
- • Chicago's First Lady Architecture Cruise
Explore Millennium Park
Millennium Park is Chicago's crown jewel, featuring world-famous public art installations. The iconic Cloud Gate sculpture (affectionately called "The Bean") offers mirror-like reflections of the city skyline. Don't miss the Crown Fountain's interactive water displays and the serene Lurie Garden.
During summer, catch free concerts at the Jay Pritzker Pavilion, designed by Frank Gehry. The park also hosts outdoor movies, yoga classes, and seasonal festivals. Winter transforms the park into a magical wonderland with ice skating and holiday decorations.
Visit The Art Institute of Chicago
The Art Institute of Chicago houses one of the world's finest art collections, spanning 5,000 years of creativity. Marvel at iconic works like Grant Wood's "American Gothic," Georges Seurat's "A Sunday on La Grande Jatte," and an extensive Impressionist collection featuring Monet, Renoir, and Van Gogh.
The museum's modern wing, designed by Renzo Piano, showcases contemporary masterpieces in a stunning space flooded with natural light. Plan at least 3-4 hours to explore the extensive galleries. Free admission days are available for Illinois residents.
Relax on the Lakefront
Chicago's 26 miles of lakefront offer endless recreational opportunities. The Lakefront Trail is perfect for biking, jogging, or leisurely strolls with stunning Lake Michigan views. Popular beaches include North Avenue Beach, Oak Street Beach, and Montrose Beach.
Navy Pier, Chicago's most-visited attraction, features restaurants, shops, the Centennial Wheel, and seasonal fireworks. The pier also hosts cultural events, boat tours, and the Chicago Children's Museum. Sunset walks along the pier offer spectacular photo opportunities.
Experience Deep-Dish Pizza
No Chicago visit is complete without savoring authentic deep-dish pizza. This iconic dish features a thick, buttery crust filled with layers of cheese, toppings, and chunky tomato sauce. Top spots include Lou Malnati's, Giordano's, and Pequod's Pizza.
For a true local experience, also try Chicago-style hot dogs (never with ketchup!), Italian beef sandwiches, and the city's thriving food hall scene. Eataly Chicago and Time Out Market offer diverse culinary options under one roof.
Explore Magnificent Mile
Michigan Avenue's Magnificent Mile is a shopper's paradise, featuring over 460 stores ranging from luxury boutiques to flagship department stores. The iconic stretch includes architectural landmarks like the Wrigley Building, Tribune Tower, and the historic Water Tower.
Even window shopping is entertaining along this bustling boulevard. The area hosts seasonal events including the Magnificent Mile Lights Festival in November and summer art fairs. Nearby, Chicago's Loop district offers additional shopping and dining options.
Discover Chicago's Music Scene
Chicago is the birthplace of modern blues and a jazz powerhouse. Experience authentic blues at legendary venues like Buddy Guy's Legends, Kingston Mines, and Rosa's Lounge. The Chicago Blues Festival in June brings world-class performers to Millennium Park.
The city's music scene extends beyond blues. Catch live jazz at the Green Mill (a former speakeasy), see indie bands in Wicker Park, or attend world-class performances at the Chicago Symphony Orchestra. Lollapalooza in August draws international music fans.
Visit Museum Campus
Museum Campus is a 57-acre park housing three world-renowned institutions: the Field Museum of Natural History, Shedd Aquarium, and Adler Planetarium. The Field Museum features Sue, the largest and most complete T. rex skeleton ever discovered.
Shedd Aquarium showcases 32,000 aquatic animals from around the world, including beluga whales, dolphins, and sea otters. The Adler Planetarium offers immersive space exhibitions and stunning skyline views. Consider purchasing a CityPASS for discounted admission to multiple attractions.
Explore Diverse Neighborhoods
Chicago's neighborhoods each offer unique character and experiences. Wicker Park and Bucktown feature trendy boutiques, craft breweries, and street art. Andersonville showcases Scandinavian heritage with cozy cafes and independent shops.
Pilsen displays vibrant Mexican culture through colorful murals, authentic taquerías, and art galleries. Lincoln Park offers upscale dining, the free Lincoln Park Zoo, and beautiful Victorian homes. Each neighborhood provides a different perspective on Chicago's multicultural identity.
Experience Chicago's Coffee Culture
Chicago's coffee scene rivals any major city. Intelligentsia Coffee pioneered the third-wave coffee movement, while local favorites like Metropolis Coffee Company and Dark Matter Coffee offer exceptional roasts. Enjoy your coffee in architecturally stunning cafes throughout the city.
Many cafes double as co-working spaces and community hubs, perfect for experiencing local life. Don't miss unique spots like The Goddess and Grocer for gourmet coffee and brunch, or Dollop Coffee for locally roasted beans in multiple neighborhood locations.
Where to Stay in Chicago
Choose a Boulevard Stays stay in prime Chicago locations for easy access to top attractions. Our designer properties in the Loop, River North, and Near North Side put you steps from world-class dining, shopping, and cultural experiences. Enjoy modern amenities with the authentic character of Chicago's most vibrant neighborhoods.
Best Time to Visit Chicago
Chicago shines brightest from May to October when warm weather allows for outdoor festivals, lakefront activities, and al fresco dining. Summer (June-August) brings peak tourism with numerous festivals, but also higher hotel rates and crowds.
Spring (April-May) and fall (September-October) offer pleasant weather with fewer tourists and lower prices. Winter showcases Chicago's resilience with holiday markets, ice skating, and cozy indoor attractions. Come prepared for cold temperatures and occasional snow.
Getting Around Chicago
Chicago's "L" train system provides efficient transportation throughout the city. The Blue Line connects O'Hare Airport directly to downtown. Purchase a Ventra Card for convenient access to trains and buses. Many attractions are walkable in the Loop and Near North Side.
Divvy bike-share offers another great option for exploring the lakefront and nearby neighborhoods. Taxis and ride-sharing services are readily available. While having a car isn't necessary in downtown areas, it can be useful for exploring outer neighborhoods.
Your Chicago Adventure Awaits
Chicago combines Midwestern hospitality with world-class culture, architecture, and cuisine. From iconic architecture tours to lakefront beaches and vibrant neighborhoods, the city offers endless discoveries. Whether you're a first-time visitor or returning to explore deeper, Chicago never disappoints.
Book your Boulevard Stays stay and experience the best of the Windy City. From stunning skyline views to authentic deep-dish pizza, your perfect Chicago adventure starts here.