Image Credits: yeowatzup, Creative Commons 2.0
Published October 29, 2017 by

Nonstop Flights: Chicago to/from Orlando $76 r/t – Southwest

[10/29/2017 @ 11:57 AM CT] Book this fare on: Southwest, (Other Airlines: Priceline, Travelocity, Orbitz, CheapTickets, Expedia, Hotwire, BookingBuddy.)
[11/04/2017 @ 10:15 PM CT] Old post clean-up. Fare gone. Removing from deal list.

Deals are usually valid 24 to 72 hours after posting, but can expire at any time (see time-stamp).

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Southwest has round-trip flights from Chicago (MDW) to Orlando (MCO) for $76, NONSTOP. $38 each-way. Flights December to February. Origin/Destination reversible. Holiday blackouts apply. Limited availability.

Note: You can save an additional $100 if you purchase your Flight+Hotel together as a package on Southwest Vacations and apply the “USA100” coupon code. Coupon expires 10/30/17. Before you commit, always compare the prices of the individual Flights and Hotel with other hotel booking sites like HotelsCombined.

Note: United and American may be matching with inferior “Basic Economy” fares. Those will not be worth it due to the bag fees and other restrictions unless you can get around them with the appropriate credit-card perk or airline status.

Related deal: [Nonstop Flights: Chicago to/from Fort Lauderdale $64 / New Orleans $74 / Las Vegas $76 r/t – Southwest]

  • Example Dates: (Southwest / BookingBuddy) Dec 04 – Dec 06 / Dec 13 – Dec 20, 25 / Blackout: Dec 15 – Jan 15 / Jan 16 – Jan 24 / Jan 23 – Jan 27, 30 / Jan 28 – Feb 02 / Jan 31 – Feb 07 / Feb 05 – Feb 08 / Other dates: Use the Fare Calendar on Southwest Airlines. 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 site to begin your booking process so we receive credit for the referral.

  • Tips: Different booking websites will often have differing routes, prices, and availability. Before you finalize your purchase, do a quick check on Expedia, Skyscanner, and Kayak to see if any other site or airline is offering a better deal.

I was able to pull this fare up on Southwest. Screenshot taken at 12:02 PM CT on 10/29/17.

Flight Details:


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Ren P. Artemio

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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