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Southwest has round-trip flights from Dallas (DAL) Chicago (MDW) for $98-$106, NONSTOP. $48-$53 each-way. Flights mostly from February to May. Origin/Destination reversible. No Holidays. Sparse availability in March. Lost of availability after April 15th.
Note: United, Spirit, and Frontier may have fee encumbered “Basic Economy” fares available for a bit less. Keep in mind that those “cheaper” fares are often more expensive once you factor in bag fees.
Note: Southwest doesn’t charge a change-fee, so if you already booked this flight, but paid more, you should be able to re-book at the lower price and get the difference paid back to you in the form of a travel-voucher.
Note: You can save an additional $150 if you book your Flight+Hotel together as a package on Southwest Vacations and use the US150OFF coupon-code. Before you commit, always compare the prices of the individual Flights and Hotel with other hotel booking sites like Tripadvisor and Expedia.
- Example Dates: (Southwest) Feb 22 – Feb 24 / etc… / May 16 – May 19 / Other dates: Use the Fare Calendar on Southwest. There are more dates available than the ones we list here, experiment on your own.
I was able to pull this fare up on Southwest. Screenshot taken when this post was initially created. See timestamps at the top of this post.
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.
- Previous Lowest Price Average: $150
- Book this fare on: Southwest, Priceline, BookingBuddy, Travelocity, Orbitz, Expedia, CheapTickets, Hotwire.
- Link to CheapTickets.com coupon code page – Check this page on Cheaptickets.com to save about 10% to 20% on your next Hotel or Package booking.
- Link to Travelocity coupon code page – Check this page on Travelocity to save about 10% to 20% on your next Hotel or Package booking.
- Link to Orbitz coupon code page – Check this page on Orbitz to save about 10% to 20% on your next Hotel or Package booking.
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