Chicago Vacation Packages

Chicago is a vibrant city with a wealth of attractions to explore. Millennium Park is a must-see, featuring the iconic Cloud Gate sculpture, often referred to as "The Bean," and the stunning Jay Pritzker Pavilion. The Art Institute of Chicago, one of the oldest and largest art museums in the United States, is home to an impressive collection of works, including Grant Wood’s American Gothic and Georges Seurat’s A Sunday on La Grande Jatte. Don’t miss the chance to visit Willis Tower (formerly Sears Tower) and step out onto The Ledge, a glass balcony offering breathtaking views of the city from 1,353 feet above the ground.

The best time to visit Chicago is during the spring (April to June) and fall (September to November) when the weather is mild and the city’s outdoor attractions are at their best. Spring is a great time to enjoy Chicago’s parks and outdoor events, while fall offers beautiful foliage and cooler temperatures, perfect for exploring the city’s neighborhoods. Summer is also popular, with numerous festivals, concerts, and activities along Lake Michigan, but it can be crowded and hot. Winter, while cold, offers the charm of holiday lights, ice skating at Millennium Park, and fewer tourists.

Chicago is a culinary haven, especially famous for its deep-dish pizza, a must-try for any visitor. Lou Malnati's and Giordano's are two of the most iconic spots to enjoy this hearty dish, characterized by its thick crust, gooey cheese, and rich tomato sauce. Another Chicago staple is the Chicago-style hot dog, an all-beef frankfurter served on a poppy seed bun and topped with mustard, onions, relish, tomatoes, pickles, sport peppers, and a dash of celery salt—no ketchup allowed! For a sweet treat, don’t miss Garrett Popcorn, known for its addictive Chicago Mix of caramel and cheese popcorn.

Yes, Vacations by Marriott Bonvoy offers flight and hotel packages to Chicago, Illinois—a dynamic city known for its iconic skyline, deep-dish pizza, and world-class museums. These bundled vacation deals allow you to book both airfare and accommodations in one seamless transaction, often at a discounted rate. Whether you're planning to explore Millennium Park, take in views from the Willis Tower Skydeck, or enjoy live blues and jazz, you can customize your Chicago vacation package to suit your interests. By bundling your flight and hotel, you can save up to 20% and earn Marriott Bonvoy points. With access to premium Marriott hotels throughout downtown and surrounding neighborhoods, Vacations by Marriott Bonvoy makes it easy to plan an exciting urban getaway to the Windy City.