Chicago

Visit the "Windy City" with a Chicago vacation package from Southwest Airlines Vacations. Include flight, hotel, and rental car as well as tickets to Chicago activities and attractions. Chicago is located on beautiful Lake Michigan. Book your Chicago vacation package today!

CHICAGO HOTELS
Discover great accommodations available with a Chicago vacation package. Select from three, four, and five-star Chicago hotels. Find accommodations throughout the Greater Chicago area including Michigan Avenue, the Theatre District, and Downtown Chicago. Chicago hotels provide wonderful amenities including relaxing spas, fine dining, brilliant entertainment, and fabulous shopping. Add one of these great hotels to your Chicago vacation package from Southwest Airlines Vacations! See all Chicago Hotels.

CHICAGO ACTIVITIES, ATTRACTIONS, & TOURS

Navy Pier in Chicago: Experience a wonderful lakefront playground with a Chicago vacation package. Navy Pier offers more than 50 acres of parks, promenades, gardens, shops, restaurants, and attractions. Navy Pier is host to an unparalleled array of family-oriented events and entertainment. Visit Navy Pier with a Chicago vacation package from Southwest Airlines Vacations!

Sears Tower in Chicago: See far beyond the city skyline with a Chicago vacation package. Standing at 1,450 feet and 110 stories high, the Sears Tower is the tallest building in North America and the third tallest building in the world. On a clear day, guests can see across Lake Michigan to Indiana, Michigan, and Wisconsin. Visit this architectural masterpiece with a Chicago vacation package from Southwest Airlines Vacations!

Sports in Chicago: Cheer for your favorite sports teams with a Chicago vacation package! See your favorite Chicago sports teams live including the Chicago White Sox, Cubs, Bears, Bulls, and Blackhawks. Join the excitement with a Chicago vacation package from Southwest Airlines Vacations!

See all Chicago Activities, Attractions, & Tours.