Skip top navigation
dropdown calendar icon (for preloading)


Click ‘N Save®

Get our biggest deals on flights, hotel stays, car rentals, vacation packages, and more.

Sign up and save

Cheap flights from Oakland, California (OAK) to Chicago, Illinois (MDW)


Promo Code Help
What is a promo code?
A promotion code is a series of letters and/or numbers that allow Customers to receive a discount off of Southwest Airlines' published airfares.

When entering a promotion code, only fares valid for the promotion code entered will display on the following page.
Flights from Oakland, California (OAK) to Chicago, Illinois (MDW)
Flights for this route often include:
  • 7 flights before noon
  • 9 flights noon to 6 pm
  • 2 flights after 6 pm
Alternate airports served by Southwest
Flights from San Francisco, California (SFO) to Chicago, Illinois (MDW) Flights for this route often include:
  • 10 flights before noon
  • 5 flights noon to 6 pm
  • 1 flight after 6 pm
Flights from San Jose, California (SJC) to Chicago, Illinois (MDW) Flights for this route often include:
  • 11 flights before noon
  • 7 flights noon to 6 pm
  • No flights after 6 pm
  • The Southwest Travel Experience

    At Southwest, we know it takes more than great deals on discount air fares and convenient daily nonstop flights to make your trip memorable. So from booking to boarding, we offer services and features designed to help ensure your travel is hassle free.

    Find out more about the Southwest Travel Experience.

  • Here at Southwest, we pride ourselves on making it both simple and fun to fly with low fares to 70+ destinations nationwide. Our weekly Click 'n Save e-mails keep you in the know about our latest flight deals and the Southwest Travel Guide helps you plan your trip.

    Southwest is a pet friendly airlines and accepts small vaccinated domestic cats and dogs. Customers flying with a pet are subject to a pet fare.

Hotels in Chicago
congress plaza hotel at grant park

520 south michigan ave

chicago, illinois 60605

Hotel Description
The Congress Plaza Hotel & convention center is perfect for the value driven guest looking for a convenient downtown location with spectacular views of Grant Park, Buckingham Fountain and Lake Michigan. It is just short walk to the New Millennium Park, The Art Institute of Chicago, Museum Campus, Symphony Center, and the Sears Tower. The city business districts, shopping and restaurants, as well as downtown theaters and universities are also just minutes away. Chicago O'Hare International Airport (15 miles) and Midway Airport (11 miles) are easily accessible. The Congress Plaza Hotel & convention center was originally designed and built in 1893 to accommodate visitors to the Columbian World's Exposition. There are a total of 840 guest rooms, including 50 deluxe suites, many of which overlook the beautiful waters of Lake Michigan. Valet Parking: $33.00/night Garage Parking: $28.00/night.
hyatt regency chicago

151 east wacker dr

chicago, illinois 60601

Hotel Description
Rising above the Chicago River, Hyatt Regency Chicago lays adjacent to the Chicago Loop business district and the Magnificent Mile shopping and dining areas. This breathtaking hotel features 2,018 guestrooms including 119 suites, 337 new Deluxe rooms, and an exclusive Regency Club. All guestrooms feature wireless Internet access at a modern workstation. This full service hotel offers an extensive business center, a complimentary fitness center, six food and beverage outlets, wireless Internet access in public areas, and convenient indoor access to all shops and services in Illinois Center. The famous Big Bar is a perfect place to relax and enjoy a cocktail without leaving the hotel. Stetson's Chophouse, located on the hotel's first floor, was voted one of the top ten steakhouses in the city by the Chicago Tribune. The casual elegance of Networks Bar & Grill allows for a variety of dining venues in the hotel. Hyatt Regency Chicago continues to receive national awards for excellence in cuisine and hospitality.
the whitehall hotel

105 e. delaware place

chicago, illinois 60611

Hotel Description
The Whitehall Hotel remains a landmark destination in downtown Chicago, offering a very European sense of grace and grandeur. Thanks to meticulous restorations. In perfect harmony with the old world charm are modern conveniences such as a fitness center. In-room features include three multi-line telephones with voicemail, high speed internet (for fee). Step outside and you'll find that the hotel is ideally located in the heart of the Gold Coast, nestled amid the Magnificent Mile's shops, restaurants, theaters, entertainment, and the business district. The Whitehall Hotel, Downtown Chicago's True Independent Boutique Hotel, proudly and successfully endures the test of time. The hotel will exceed your expectations and invite you to explore The Whitehall Hotel today.

This property is 100% smoke free

the godfrey hotel chicago

127 w huron

chicago, illinois 60654

Hotel Description
Godfrey means peace and welcome; welcome to The Godfrey Hotel Chicago. The Godfrey Hotel Chicago offers unforgettable style from the Cubist-influenced facade to the chic accommodations, each detail of this striking new hotel has been designed with the guest's experience in mind.