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Southwest has round-trip flights from Dallas (DAL) to Chicago (MDW) or Philadelphia (PHL) starting at $80, NONSTOP. $40-44 each-way. Chicago flights from December to mid-February. Philadelphia flights from January to mid-February. Mostly Tuesdays and Wednesdays. Origin/Destination reversible. No Holidays.
Note: You may find additional savings if you purchase your Flight+Hotel together as a package on Southwest Vacations. Before you commit, always compare the prices of the individual Flights and Hotel with other hotel booking sites like Tripadvisor.
- Chicago – Example Dates: (Southwest / BookingBuddy) Dec 02 – Dec 05 / etc… / Feb 10 – Feb 13 / Other dates: Use the Fare Calendar on Southwest. There are more dates available than the ones we list here, experiment on your own.
- Philadelphia – Example Dates: (Southwest / BookingBuddy) Jan 06 – Jan 09 / etc… / Feb 10 – Feb 13 / Other dates: Use the Fare Calendar on Southwest. There are more dates available than the ones we list here, experiment on your own.
When you are ready to book your flight or hotel, please use the links on our page to begin your booking process so we receive credit for the referral.
- Tips: Vacation rentals on Vrbo are usually cheaper per night for longer stays than shorter stays. This is due to three main factors; The first is that most properties have a cleaning fee that is a fixed rate, the second is that many hosts provide discounts for stays longer than 6-days, the third is that the Vrbo service fee percentage is higher on short stays.
- Tips: You can (and should) sort the Vrbo vacation rental search results by “Total” price. Doing so exposes properties with high fees. For example, a $140 per-night property with $100 fees will rank as being more expensive than a $150 per-night property with $30 fees, when sorted. Sorting by “most reviews” is also a good option, as this will show you the most popular properties.
- Tips: Rent a car for cheaper by using Priceline’s “Express Deals”. The rental car company will be hidden until after you purchase, but this allows those companies to undercut the published rate indirectly. You can remove low quality companies from those hidden results. The trick is to use the quality filter on their website to remove any rental car company with a review rating under 7.0 and then pick the deals that survive the filter.
- Tips: Use Tripadvisor to create a Hotel “short list”. First, plug in your dates and destination. Then select “Sort by Traveler Ranked”. Finally, select the “Traveler Ranking” filter to show “only 4* and up”. Use this resulting “short list” of hotels to find the cheapest one with a high ranking.
- Tips: Hotel rates for Weekend dates are usually higher than the rates for Sunday through Thursday. Tripadvisor has a color-coded date calendar, red when the average hotel price for that day is more expensive, green for less expensive. You can use this to get an overview of what dates in the month are at a discount.
- Tips: Different booking websites will often have differing routes, prices, and availability. Before you finalize your purchase, do a quick check on BookingBuddy, Skyscanner, and Kayak to see if any other site or airline is offering a better deal.
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I was able to pull this fare up on Southwest. Screenshot taken at 3:22 PM on 10/10/17.
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.
- Full Route: DAL-MDW / PHL-DAL
- Previous Lowest Price Average: MDW = $125 / PHL = $175
- 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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- Airfare + hotel: Priceline, Travelocity, Orbitz, CheapTickets.com, Expedia, Hotwire, Skyscanner, Kayak
- Vacation rentals: Vrbo
- Airlines: Iberia, Hawaiian Airlines, Lufthansa, Swiss, Qatar Airways, Emirates, KLM
- Hotel search: TripAdvisor, Hotels.com, HotelsCombined.com, Booking.com, Agoda
- Car rental: Priceline, Rentalcars.com
Flights departing from a different city (our other websites):
- Flights from New York
- Flights from Chicago or Milwaukee
- Flights from Los Angeles (LAX, ONT, BUR, LGB, SNA)
- Flights from Seattle
- Flights from Portland, Oregon (PDX)
- Flights from Phoenix
- Flights from Denver
- Flights from Austin or San Antonio [Escape ATX]
- Flights from Houston [Escape Houston]
Other Useful Links:
- [Budget Travel] – list all the posts that deal with Budget Travel (filter out all the flight deal posts)