Chicago Vacations from $221

Downtown Chicago: Ideal for first-time visitors, Downtown Chicago offers easy access to iconic attractions like Millennium Park, Navy Pier, and the Magnificent Mile shopping district. Visitors can choose from a variety of hotels ranging from luxurious upscale properties like The Langham, Chicago to more budget-friendly options, like the Hilton Garden Inn Chicago McCormick Place. 

The Loop: Located in the heart of downtown, The Loop is known for its skyscrapers, theaters, and cultural attractions like the Art Institute of Chicago and the Chicago Symphony Orchestra. Hotels near The Loop are a great choice for those interested in history, architecture, and the arts. 

River North: This trendy neighborhood is known for its vibrant nightlife, art galleries, and upscale dining scene. Visitors staying at hotels close to River North like The Royal Sonesta Chicago River North or 21c Museum Hotel Chicago can enjoy easy access to attractions like the Museum of Contemporary Art and the Chicago Riverwalk. 

Lincoln Park: Situated just north of downtown, Lincoln Park is known for its leafy streets, historic homes, and the sprawling Lincoln Park Zoo. Enjoy boutique shopping, charming cafes, and easy access to the lakefront when you stay here at an affordable option like the Hotel Lincoln, or really splash out for a luxurious trendy experience at Claridge House, which is close to the park. 

Iconic landmarks: Choose hotels near Millennium Park, like The Westin Chicago River North or the upscale Kinzie Hotel, where you can marvel at the famous Cloud Gate sculpture and enjoy interactive exhibits at the Crown Fountain. Take a leisurely stroll along the Lakefront Trail or hop on a sightseeing cruise on Lake Michigan for breathtaking views of the city skyline. Stay in hotels near Lincoln Park to visit the Lincoln Park Zoo, one of the oldest zoos in the United States, which offers free admission and is home to a diverse array of animals from around the world, sure to delight visitors of all ages. 

Museums and cultural attractions: Discover Chicago's rich cultural heritage at world-class museums like the Field Museum, home to Sue the T. rex, and the Museum of Science and Industry, where interactive exhibits ignite curiosity in visitors of all ages. Don't miss the Shedd Aquarium and Adler Planetarium for immersive learning experiences. Many museums and attractions offer special exhibits and programs designed specifically for families, providing engaging and educational opportunities for children to learn while having fun. 

Entertainment and shows: Catch a Broadway musical or comedy show at one of Chicago's renowned theaters like the Cadillac Palace Theatre or the Chicago Shakespeare Theater. Experience the magic of live performances at Navy Pier's iconic Crystal Gardens or the Chicago Children's Theatre. There's also the Chicago Children's Museum at Navy Pier, where hands-on exhibits and interactive play areas spark creativity and imagination in young visitors. 

Sporting experiences: Chicago boasts a rich sporting culture with attractions that cater to both fans and athletes alike. Key highlights include iconic venues like Wrigley Field and Soldier Field, home to the Chicago Cubs and Chicago Bears, respectively. Basketball enthusiasts can catch NBA games at the United Center, where the Chicago Bulls play. Additionally, the city offers opportunities for outdoor activities, such as golfing along Lake Michigan or sailing on the Chicago River. For those interested in sports history, the Chicago Sports Museum at Water Tower Place provides an immersive experience showcasing the city's athletic legacy. 

Experience the vibrant cultural scene of Chicago with Expedia's vacation packages, and immerse yourself in the city's rich heritage and artistic flair. Stay close to iconic landmarks at citizenM Chicago DowntownOpens in a new window or Hyatt Regency ChicagoOpens in a new window, and easily visit Millennium Park and the Art Institute of Chicago, where you can explore world-class exhibits and outdoor art installations. For a truly unique experience, opt for accommodations near the historic neighborhoods of Pilsen or Hyde Park, like The Hoxton ChicagoOpens in a new window with its rooftop swimming pool, or the Sophy Hyde ParkOpens in a new window, which boasts excellent guest reviews. 

Browse Expedia's selection of Chicago vacation packagesOpens in a new window to find the perfect combination of flights, accommodations, car rental, and more. With Expedia, planning your Chicago getaway is simple and stress-free. Take advantage of special package deals and discounts on flights and hotels to Chicago, allowing you to maximize your savings while enjoying all that the city has to offer. Additionally, consider booking activities and attractions in advance to secure your spot and avoid long lines during your trip to Chicago.