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Now accepting reservations through 4/6/15.


Traveling with an infant?

Booking an Infant?

Children ages 2 or older are required to purchase an air seat for all travel.

For Travel within the United States and Puerto Rico:
To reserve an air seat for your infant, please enter the age of the infant as 1. If your infant will be traveling as a Lap Child, arrangements can be made upon arrival at the airport with proper age verification. Proof of age (i.e. Birth Certificate or Passport) is required for all infants and children at time of airport check-in.

For Travel to Mexico and The Caribbean:
To reserve an air seat for your infant, please enter the age of the infant as 1. If your infant will be traveling as a Lap Child, you must contact our Customer Care Center to make arrangements for a Lap Child on an international flight. Please note that hotel may assess a charge when adding an infant to your room reservation. A valid Passport is required for all infants and children at time of airport check-in.

If you have additional questions please contact our Customer Care Center at 1-800-243-8372 for assistance with your booking.


 

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Chicago, IL Vacations

Known for its snowy winters, vibrant city atmosphere, and world-class dining, shopping, and accommodations, Chicago truly is a world-class destination. Glide across the ice with Millennium Park ice skating, 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.

  • Deals, Hotels, and Activities
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Chicago, IL Deals from Newark (EWR)
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    • Tremont Chicago

      Save up to $100 + Free Room Upgrade

      Valid departure date(s): 10/21 - 2/28


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Featured Chicago, IL Hotels

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

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    Sheraton Chicago Hotel & Towers

    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

    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

    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

    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 Magnificent Mile

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

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    Chicago's Essex Inn

    This intimate hotel provides excellent views of the city, Grant Park and Lake Michigan.


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

Chicago

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 up to $120 roundtrip per person 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, & 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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First and second checked bags. Weight and size limits apply. A golf bag can be substituted for one checked bag. Checked baggage fee comparison is based on Southwest = 1st and 2nd bag free vs. "The Other Guys" = 1st bag $25/one-way; 2nd bag $35/one-way; or 2 bags $60/one-way and $120/roundtrip. Source: farecompare.com.


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