Cheap Flights: Dallas to Chicago $80-$100 NONSTOP r/t – Southwest + Others

[09/20/2014 @ 1:25 PM] Open this itinerary here: Southwest AirlinesExpediaOrbitz, Priceline, Travelocity, BookingBuddy.
[10/03/2014 @ 5:23 PM] Price has dropped to $104 from $115.
[10/16/2014 @ 12:10 PM] Price fluctuates between $87 and $116.
[12/31/2014 @ 4:22 PM] Updated with most recent price. $81 / United and American.
[01/23/2014 @ 4:23 PM] Updated with most recent price. $105.
[02/02/2015 @ 1:33 PM] Updated with most recent price. $87.
[05/04/2015 @ 4:52 PM] Updated calendar, price and example dates.
[05/13/2015 @ 5:57 PM] Price has increased to $137, not bad, but I’m going to remove it from the deal list anyway.

We now cover Cheap flights departing FROM Chicago on our sister publication, Escape Flights – Chicago.

Southwest Airlines is offering NONSTOP flights from Dallas (DAL) to Chicago (MDW) for $82 round-trip ($41 each way). Flights are available midweek, May to June. Fare is reversible.

This fare is often matched by United and American via DFW and ORD. As of the time of this writing, United is matching this sale.

This is one of the longest running deals due to the added competition coming from Southwest since the lifting of the Wright Amendment last year. This deal has been around forever now and the price has fluctuated from the $80 to $115.

When you are ready to book, please use the links on our site to begin your booking process so we receive credit for the referral.

Flight Availability: Dallas to Chicago as of 4:53 PM on 5/4/2015.
Flight Availability: Dallas to Chicago as of 4:53 PM on 5/4/2015.

When you begin your search for a Hotel or Vacation Rental in Chicago please use our TripAdvisor: Chicago link to find a good place to stay. Booking your trip as a Flight + Hotel package will probably save you more money than if you were to book separately. Be sure to make use of any coupon codes for Hotels that may be available at the bottom of this post.

Flight Details:

  • Availability: See Calendar. Use the flexible date calendar on Southwest’s site to find date pairs.
  • Documentation: Domestic Flight.
  • Departure and Destination Airports: DAL -MDW
  • Example Dates: Southwest Airlines ( May 19 – May 27
  • Example Dates: Other Airlines (Priceline)  May 27 – Jun 03 / Jun 03 – Jun 07 / Jun 02 – Jun 10
  • Carrier: US Airways / American Airlines / Southwest Airlines / United
  • Fare Basis Code
  • Fare Class:
  • Mile Accrual: Depends on carrier.
  • Stopover component: none.
  • CPM: 5.42 (1604 miles)
  • Full Route: DAL-MDW or DFW-ORD
  • Previous Low Price: $80-$100 on 04/01/15.
  • Open this itinerary on: Southwest AirlinesExpediaOrbitz, Priceline, Travelocity, BookingBuddy.

Destination information:

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Want travel coupon codes? Go here: [Coupon Codes for Orbitz,, Travelocity and Priceline].