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Chicago vacations

Book a Chicago vacation package from Southwest Vacations® that includes low cost airline tickets to Chicago, hotels, rental cars, activities and attractions.
Chicago is a city unlike any other. We’ve got the architectural marvels, world-class museums, dynamic entertainment, and award-winning dining scene you’d expect from one of the world’s greatest cities. But we’re more than just another big city—our welcoming residents, inclusive neighborhoods, and Midwestern soul truly make Chicago the city that feels like home. Ready to explore Chicago? Check out our vacation packages to start your exploration with Chicago's unique style.

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Here are a few of our most popular Chicago resorts:

  • Exterior

    Chicago-Midway

    Sheraton Grand Chicago

    Offering spectacular views of the Chicago River, Lake Michigan or the city skyline, this grand hotel is one of Chicago's superior riverfront destinations.

  • Exterior

    Chicago-Midway

    The Westin Michigan Avenue Chicago

    Located on the Magnificent Mile this hotel offers a relaxing oasis after a day exploring the Windy City.

  • Exterior

    Chicago-Midway

    W Chicago - City Center

    Set in the heart of Chicago's famed 'Loop', this vibrant hotel provides quality amenities and classic service.

Things to do in Chicago, IL

  • Hancock Tower Tour

    Chicago Grand Tour & Hancock Tower Tour

    A comprehensive tour of everything that Chicago has to offer. You'll travel through both the North and South side business and residential districts. North side tour - this tour is for those looking to experience the vitality and excitement of Chicago.
  • City of Chicago

    Hop On and Hop Off Trolly Tour

    The Hop On and Hop Off Tour by Chicago Trolley & Double Decker tour guides provide riders with an amusing and informative look at Chicago history as the tour winds through a 13 mile route. 
  • Macy's Star Shopper Logo

    Macy's Star Shopper - State Street

    You're a star at Macy's! Receive VIP treatment from the world's largest department store! Enjoy a memorable shopping experience that only Macy's can provide. Begin your experience at the Macy's Visitor Center, where our staff will greet you and give you insider information on the best that the city has to offer. Feel free to relax at your leisure before enjoying your tour.

Family activites to do in Chicago, IL

  • Dinosaur field museum of natural history

    The Field Museum

    The Field Museum is an educational institution concerned with the diversity and relationships in nature and among cultures. Combining the fields of Anthropology, Botany, Geology, Paleontology and Zoology, the Museum uses an interdisciplinary approach to increasing knowledge about the past, present and future of the physical earth, its plants, animals, people, and their cultures. 
  • Family Enjoying Pizza

    Chicago Pizza Tour

    Delivering a taste of Chicago’s renowned pizza legacy, you can expect to meet your local tour guide at a significant pizzeria in the downtown area. Start by hearing the history of Chicago deep dish while sampling a slice from one of the best purveyors of the style.
  • Science Park at Chicago

    Museum of Science and Industry

    The Museum of Science and Industry's unique and cutting-edge experiences and exhibits have earned some bragging rights. Check out some of the most popular exhibits like Science Storms, which explores nature's most powerful phenomena. Witness bolts of lightning flashing above you, trigger an avalanche, create a tsunami, and more.

Known for its vibrant city atmosphere, and world-class dining, shopping, and accommodations, Chicago truly is a world-class destination. Get up-close-and-personal with wildlife at Lincoln Park Zoo or enjoy the attractions at Navy Pier. Chicago's flourishing arts and entertainment scene has some of the finest live music, comedy, dance, and opera in the country. Let Southwest Vacations help you plan a Chicago vacation package full of sports, shopping, and endless entertainment.