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Chicago, IL

Chicago vacations

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.

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Featured Chicago hotels

These are just a few of our available hotels in Chicago, we have many more available! Perform a search to see all the options Southwest Vacations® has to offer.

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    Sheraton Grand Chicago

    4 star hotel rating

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

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    The Westin Michigan Avenue Chicago

    4.5 star hotel rating

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

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    W Chicago - City Center

    4 star hotel rating

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

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    W Chicago - Lakeshore

    4 star hotel rating

    Experience Chicago from an entirely different view during visits to this picturesque Chicago escape. The only lakefront hotel in Chicago, guests of the hotel are treated to spectacular views of Lake Michigan and easy access to all of the shops, dining and entertainment of nearby Navy Pier.

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    InterContinental CHICAGO

    4.5 star hotel rating

    Located on Michigan Avenue this hotel is a historic city landmark and features a contemporary interior.

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    Palmer House A Hilton Hotel

    4 star hotel rating

    Where old world elegance blends with the modern amenities of today, this inspired hotel offers luxury travelers, spa-lovers and shopping-enthusiasts with an upscale oasis in the heart of sweet home Chicago.

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    The Drake

    4 star hotel rating

    Blending old world elegance, personalized service and a great location, this superior hotel has been a Chicago landmark since its opening in 1920

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    Hilton Chicago

    4 star hotel rating

    This lavish downtown retreat has achieved an unprecedented fusion of historic luxury and contemporary amenities. Located in the heart of Chicago's cultural core, guests of the hotel enjoy superior amenities, a selection of restaurants, an athletic club and a convenient location nearby popular museums, theaters and nightlife.

Featured things to do

Here are just a handful of activities available. We have tons more! You can add these and many others to your vacation package during the booking process.

Chicago, IL


Visit the "Windy City" with a Chicago vacation package from Southwest 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 and save because bags fly free with Southwest Vacations.

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 Vacations.

Chicago activities, attractions, and 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. With host an unparalleled array of family-oriented events and entertainment, Navy Pier is the perfect attraction for the whole family. Visit Navy Pier as a part of your customized Chicago Family Vacation Package with Southwest 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 one of the tallest buildings in America and the world. On a clear day, guests can see across Lake Michigan to Indiana, Michigan, and Wisconsin. Visit this architectural masterpiece with a with a Southwest Vacations package to Chicago.

Sports in Chicago: Cheer for your favorite sports teams with a Chicago Sports Vacation Package. See your favorite Chicago sports teams live including the Chicago White Sox, Cubs, Bears, Bulls, and Blackhawks. Join the excitement with live action from your favorite professional sports teams.

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