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Here are a few of our most popular Chicago resorts:

  • 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.

    4 star hotel rating

  • The Westin Michigan Avenue Chicago

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

    4.5 star hotel rating

  • W Chicago - City Center

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

    4 star hotel rating

  • W Chicago - Lakeshore

    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.

    4 star hotel rating

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Chicago deals from Washington DC - Dulles (IAD)

Southwest Vacations makes it easy to plan the best vacation for your budget, offering weekly deals on travel and resorts. Check out our deals page for more exciting offers.

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    Featured things to do:

    Southwest Vacations has activities, tours, and attractions to add to your vacation. View all of your options in the Things to Do section during the booking process.

    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. ​

    First and second checked bags. Weight and size limits apply. A golf bag can be substituted for one checked bag.

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