Image Credits: Daniel Schwen, Creative Commons 4.0
Published December 14, 2016 by

Nonstop Flights: Dallas to/from Chicago $88 r/t – Southwest / United

[12/14/2016 @ 2:26 PM] Book this fare on: Southwest Airlines, (Other Airlines: Priceline, Travelocity, Orbitz, CheapTickets, Expedia, BookingBuddy)

The prices and details in this post were accurate when this post was last updated (see time-stamps above). Prices and availability of this deal can and will change, given enough time. This website contains references to airfare and accommodation from companies that compensate this site when you click on their link or purchase travel from their sites.

Southwest and United have round-trip flights from Dallas (DFW/DAL) to Chicago (ORD/MDW) for $88, NONSTOP. $44 each way. Flights are midweek TUE/WED January to April. Origin/Destination reversible. Expect prices to fluctuate +/- $10.

Note: United only has flights in January and February. Southwest has much better availability.

Note: This destination is on sale very often, usually in the range of $77 to $107 for midweek flights.

  • Example Dates: SOUTHWEST (Southwest Airlines) Jan 11 – Jan 18 / Jan 17 – Jan 24 / Jan 18 – Jan 25 / Jan 31 – Feb 07 / Feb 01 – Feb 08 / Feb 07 – Feb 14 / Feb 15 – Feb 22 / Feb 21 – Feb 28 / Mar 01 – Mar 08 / Mar 07 – Mar 14 / … etc / Apr 12 – Apr 19 / Other dates: Use the Fare Calendar on Southwest.
  • Example Dates: UNITED (Priceline / Travelocity) Jan 11 – Jan 18 / Jan 17 – Jan 24 / Jan 18 – Jan 25 / Jan 31 – Feb 07 / Feb 01 – Feb 08 / Feb 07 – Feb 14 / / Other dates: Try any TUE/WED flight between January 10th and February 15th.
  • United and Southwest usually match fares for this route. Before you finalize your purchase, you may want to check your dates on BookingBuddy to see if any of the other airlines are offering a better deal.
  • If you want to see other deals that are still bookable you should check out the “Bookable Deals” page on our site. It filters out deals that have expired, or have low availability.

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

I was able to pull this fare up on Southwest and Priceline, and it should be available on all of the other booking sites. Screenshot taken at 2:36 PM on 12/14/16.

If you plan on booking a hotel, use our travel coupon codes to save up to 15% to 20% off. Alternatively, you may be able to save the most money by booking your trip as a Flight + Hotel package on Priceline, Orbitz, or Travelocity.

If you want to see other deals that are still bookable you should check out the “Bookable Deals” page on our site. It filters out deals that have expired, or have low availability.

Note: OTAs such as Travelocity and Priceline allow free cancellation without penalty within 24-hours after you purchase. As deals sell-out or expire quickly, this policy will allow you to “lock-in” the cheap fare while you sort out a plan. Just keep in mind that after 24-hours, you will not be able to cancel without the regular penalty. On Travelocity, you can easily see if your ticket allows a free cancellation, just look for “FREE Cancellation within 24-hours” next to the booking button.

Most airlines also offer 24-hour free cancellation with varying policies. For example American Airlines allows you to “Hold” a ticket before payment for 24-hours but once you pay for it you can’t cancel without a change fee or penalty, even if it was purchased less than 24-hours ago.

Flight Details:

Destination information:


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Ren P. Artemio

Ren is the Chief Director of Nap Times at Escape Houston, Escape ATX, Cheap DFW, and Escape Flights. He really likes researching airfare and the travel industry, especially when it means getting a cheap flight to anywhere (he's not picky).

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