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- One-Way As Low as $149 | SFO to MDW Flights
  https://www.southwest.com › Southwest › Flights
  SponsoredFirst Travel Date Available: 2/20/2025. Seats/dates/mkts. Lmtd; restr/excl apply. Looking For Low Fares & Flexible With Travel Dates? Shop Our Low Fare Calendar Today!
  Types: Nonstop Flights, Round Trip Flights, One-Way Flights, Last Minute Flights
- San Francisco to Chicago | Flights from $184
  https://www.kayak.com › sfo-chi
  SponsoredSan Francisco To Chicago. Book the Best Flight to Your Next Destination and Save! Compare 100s of Flights & Airline Tickets. Your Shortcut to the Best Travel Deals.
  Easy & fast booking · Metasearch Travel Leader · Search one and done · Find the right flight
- San Francisco - Chicago | Flights from $184
  https://www.cheapflights.com › sfo-chi
  SponsoredSan Francisco To Chicago. Filter results and book your perfect flight easily. Better deals with one easy search. Compare cheap flights to find your best fit.
  Types: Low Cost, Economy, Premium Economy, Business Class, First Class