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Southwest has round-trip flights from Dallas (DAL) Chicago (MDW) for $98, NONSTOP. $48 each-way. Flights mostly from January to March. Origin/Destination reversible. No Holidays.
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 $125 if you book your Flight+Hotel together as a package on Southwest Vacations and use the 125DOM19 coupon-code. Before you commit, always compare the prices of the individual Flights and Hotel with other hotel booking sites like Hotels.com or HotelsCombined.
- Example Dates: (Southwest) Jan 10 – Jan 12 / etc… / Mar 01 – Mar 06 / 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.
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.
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.
Relevant Coupon Codes for Travel:
- Orbitz.com: LINK TO COUPON CODE: Save 15% to 20% Hotels. On Orbitz, scroll page to “Today’s Top Deals” for the coupon-code.
- CheapTickets.com: LINK TO COUPON CODE: Save 15% to 20% Hotels.
- Southwest Vacations: LINK TO COUPON CODES:Various coupons for Southwest Flight+Hotel packages.
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- Airfare + Hotel: Priceline, Travelocity, Bookingbuddy, Orbitz, CheapTickets.com, Southwest Vacations, Expedia, Hotwire
- Airlines: Iberia, AirFrance, Hawaiian Airlines, Lufthansa, Swiss, Qatar Airways, Emirates, KLM
- Hotel Search: TripAdvisor, Hotels.com, HotelsCombined.com
- Travel Guides and Accessories: Lonely Planet
Other Useful Links:
- [Bookable Deals] – list all the other great travel deals that are still alive and bookable.
- [Budget Travel] – list all the posts that deal with Budget Travel (filter out all the flight deal posts)
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