Chicago Vacation Packages

Make the most of your trip to Chicago by experiencing one of our vacation packages:

Blue Man Group Vacation Package - Blue Man Group, one of Chicago's longest-running shows, is a unique audiovisual experience—vibrant, colorful, and hilarious. Family-friendly and fabulously blue, this critically acclaimed show features innovative music and technology combined with good-humored social commentary. Book Now!

360 Chicago Vacation Package - Soaring 1,000 feet over Chicago’s legendary Michigan Avenue, 360 CHICAGO is one of the city’s most unique attractions. 360 CHICAGO offers breathtaking views of Chicago’s lakefront, magnificent skyline and four neighboring states. Book Now!

Skydeck Vacation Package - No trip to Chicago is complete without a visit to the The Ledge at Skydeck Chicago! Enjoy 360-degree views spanning up to 50 miles and 4 states and our most spectacular view—1,353 feet straight down! "Dare to Stand Out" on The Ledge—glass balconies extending 4.3 feet outside the building provide a thrilling, once in a lifetime experience! Book Now!

Adler Planetarium Package - Explore the outer reaches of the universe at Chicago's Adler Planetarium, the first planetarium in the United States. Learn about space at the most advanced and oldest planetarium in existence today, with a plethora of shows and exhibits to delight visitors of all ages. Discover must-see shows like Cosmic Wonder, Destination Solar System and Skywatch Live and exhibits like Mission Moon, Our Solar System and the Universe: A Walk Through Space and Time. Admission includes choice of two Sky Shows and tour of historic Atwood Sphere. Book Now!

CityPASS® Vacation Package - The Chicago CityPASS® program covers admission to five top attractions. Plus, CityPASS® ticket holders skip most main-entrance ticket lines. Each CityPASS® ticket book contains helpful information, including insider tips, an attraction location map, attraction and transportation details, directions, and money-saving coupons. Book Now!

Chicago Crime Tours - Escape into Chicago's underworld on a crime and mob tour with Chicago Crime Tours. Some of the world’s most famous criminals, mobsters and gangsters bamboozled their way through Chicago. Sit comfortably on a climate controlled bus and enjoy sightseeing famous Chicago crime scenes from the 19th century through modern times.  Book Now!

Big Bus Vacation Package - Our sightseeing bus tours of Chicago take you on an extensive route, showcasing the best the city has to offer. From the great vantage point of our double-decker buses, you'll enjoy panoramic views of Chicago’s finest skyscrapers, including the John Hancock Center, the Willis Tower and the Wrigley Building. Book Now!

Chicago Trolley and Double Decker Vacation Package - Chicago is a cultural, architectural, and historic showcase. Your tour ticket gives you rides, guides and the chance to make this city your own. Ride The Red & Green Trolleys® and our Big Red Double Decker Buses. Your Hop On Hop Off Tour ticket gives you transportation to famous Chicago attractions. You will enjoy our two hour Downtown Tour, covering 13 miles of Chicago's downtown. Book Now!

Architecture Walking Tour Package - The Best Architecture Walking Tour Since Sliced Bread is a creative tour of Chicago architecture, designed for curious people. You will learn about architectural styles through their connections with technology and culture, including pop culture. We’ll look at lots of eye candy while expanding our understanding of architectural styles and Chicago history. It’s a very visual and interactive tour. Book Now!

1893 World's Fair Tour Package - This very special walking tour digs into how and why the 1893 World’s Fair captures our imaginations more than any other event in Chicago history. Unlike other World’s Fair tours and Devil in the White City tours, which likely revolve around facts and trivia, we dig deeper. We dug through archives, studied photographs, and designed games to devise a fun and insightful walking tour. Book Now!