Skip to content
Depart date Return date
Search vacations and save

Now accepting reservations through April 7, 2019.

Children ages
Must select age at time of travel (each child under 18)
Children ages
Must select age at time of travel (each child under 18)
Children ages
Must select age at time of travel (each child under 18)
Children ages
Must select age at time of travel (each child under 18)
Traveling with an infant?


Fly to Midway International Airport and discover Chicago. Plus, save up to $100 on your vacation.

Book a flight + hotel vacation package of $750 or more to Chicago, and save up to $100 when you use the promo code 75CHI at the time of booking.*

  • Save $75 on packages of $750 – $1,499.
  • Save $100 on packages of $1,500 or more.

Book: 8/28/18 – 10/1/18 by 6:00 p.m. CT
Travel: 8/29/18 – 12/19/18
One-day advance purchase is required.

Chicago is more than just a big city. Besides its striking downtown, which includes some of the tallest buildings in the world, Chicago has a distinctive shoreline, hundreds of vibrant parks, and 77 unique neighborhoods. It's this truly distinctive mix of global attractions and local charm that make Chicago one inspiring city.

Shop featured hotels to complete your package.

  • Palmer House, A Hilton Hotel

    Star Rating

    • The longest operating hotel in North America and inventor of the brownie.
    • Steps to Millennium Park and the Art Institute of Chicago.
  • The Westin Michigan Avenue Chicago

    Star Rating

    • Located on the Magnificent Mile; across from Bloomingdale's and the upscale shops of Water Tower Place. 
    • Refresh your mind and spirit with Westin WORKOUT®, SuperFoods Rx, Heavenly Bed®, and Heavenly Bath®.
  • Hyatt Regency Chicago

    Star Rating

    • Stunning city, Chicago River, and Lake Michigan views with all the comforts of a modern, urban getaway. 
    • Five dining experiences at Hyatt Regency Chicago: an urban steakhouse and sushi bar, one of the largest hotel bars in the city, farm-to-fork fare, and a quaint small plates eatery.
  • The Drake, A Hilton Hotel

    Star Rating

    • Direct access to Oak Street Beach, anchoring the north end of The Magnificent Mile fashion district.
    • Home of Coq d’Or—steeped in nearly a century of tea service tradition, and was the second bar establishment following the repeal of prohibition and Palm Court.
  • Hilton Chicago

    Star Rating

    • USA Today Top 20 Chicago hotel.^
    • Across from Grant Park in the vibrant Cultural Mile.
  • Sheraton Grand Chicago

    Star Rating

    • Standing right behind the River Esplanade Park, the Sheraton Grand Chicago is within walking distance of the Navy Pier.
    • This hotel calls out to families with generously sized rooms and a large indoor pool.
  • Thompson Chicago

    Star Rating

    • Located in the heart of Chicago’s Gold Coast neighborhood and one block from Magnificent Mile and Oak Street shopping.
    • All rooms benefit from spectacular city and/or Lake views.
  • Swissotel Chicago

    Star Rating

    • Designed by renowned Chicago architect Harry Weese.
    • Fabulous wrap-around views from Navy Pier to Millennium Park.
  • Loews Chicago Hotel

    Star Rating

    • Located less than a mile from Navy Pier.
    • Flavor Chicago brings an authentically local culinary experience directly to you on property.
  • Omni Chicago Hotel

    Star Rating

    • The only all-suite luxury accommodations on Michigan Avenue.
    • Rooftop garden of fruits, vegetables, and herbs.
Customized vacation packages include:
  • Round trip flight via Southwest Airlines®.
  • Hotel accommodations (including taxes).
  • Bags fly free®† with Southwest Vacations®. Even golf bags fly free®.

Learn more about the benefits of booking with Southwest Vacations.
*Up to $100 per reservation promotion code savings apply on flight + hotel vacation packages of $750 or more to Chicago (Midway) (MDW). Save $75 on packages totaling $750 – $1,499; Save $100 on packages totaling $1,500 or more. Savings is reflected in the package price when using promotion code 75CHI at the time of booking and is based on total package price before discount is applied. Length of stay for flight and hotel components must match. Promotion code intended for redemption by individual consumer only. One-day advance purchase is required. Savings valid if booked 8/28/18 – 10/1/18 by 6:00 p.m. CT for travel 8/29/18 – 12/19/18.

^According to USA Today’s The 20 most popular hotels in Chicago in April 25, 2017.

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

Seats are limited and may not be available on some flights that operate during peak travel times and holiday periods. Flight and hotel rates may vary by day of week. Hotel surcharges may apply to weekends, holidays, and convention periods. Flights available on published, scheduled service only. Rates may be subject to change until purchased. Discounts are valid per reservation before taxes are applied. Offer not valid on existing reservations and may not be combined with any other offer. Subject to availability. Restrictions apply. The Mark Travel Corporation is the tour operator for Southwest Vacations.
Keyboard Instructions
change date: Ctrl/Command + ///
previous/next month: Page Up/Down
select date: Enter
cancel and close: Esc