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Now accepting reservations through June 8, 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 Chicago Midway International Airport and discover Chicago. Plus, save up to $100 on your vacation.

Book a flight + hotel vacation package of $500 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 $500 – $1,499.
  • Save $100 on packages of $1,500 or more.

Book: 9/25/18 – 12/30/18 by 6:00 p.m. CT
Travel: 9/26/18 – 12/31/18
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.

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 $500 or more to Chicago (Midway) (MDW). Save $75 on packages totaling $500 – $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 9/25/18 – 12/30/18 by 6:00 p.m. CT for travel 9/26/18 – 12/31/18.

^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.
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