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Now accepting reservations through August 6, 2018.

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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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Chicago deals from Newark (EWR)

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.

  • The James Chicago

    Save $125 + Apartment Suite upgrade

  • Valid departure date(s): 11/21 - 8/06

Featured Chicago hotels

Here are a few of our most popular Chicago resorts. Perform a search above to see all of the hotel options Southwest Vacations has to offer.

  • 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.

  • 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.

  • 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.

  • 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.

  • Hyatt Regency Chicago

    4 star hotel rating

    Discover the difference and experience the sophistication at our downtown Chicago hotel.​

  • 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.

  • The Drake Hotel

    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

  • 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

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.

Learn about Southwest Vacations' travel protection. Be protected from the unexpected. Learn about bags fly free.  Applies to your first and second checked bags. Weight and size limits apply. Sign up for exclusive offers, get deals and special offers delivered directly to your inbox.

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

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