Amazing: $44 Flights From Chicago To Florida On Southwest And American Airlines

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American Airlines released some crazy good fares yesterday for flights between Chicago O’Hare and Orlando, and Chicago O’Hare and Tampa, with travel as low as $86.20 ROUND TRIP on selected dates in January and February, 2015.Screen Shot 2014-12-17 at 6.53.33 PMSouthwest Airlines decided to match some of those crazy good fares from Chicago Midway to Orlando, and Chicago Midway to Tampa with their own $86.20 ROUND TRIP fare.Screen Shot 2014-12-17 at 6.56.39 PMThe flights to Tampa on both airlines add about $12 to the  – for a total of $98.20 ROUND TRIP.

The crazy good fares seem to be available on Tuesdays, Wednesdays and Saturdays in January and February 2015.  Southwest makes it easy to find their best fares by using the “Low Fare Calendar” found on, while fares on American can be searched on or searchable using the ITA Software Matrix Airfare Search. Also, since these are one-way fares, and if you are willing to be flexible, you could take one carrier down, and the other carrier back.

Bottom Line:

It’s a great time to get out of the cold of Chicago and into sunny Florida during the winter months. It’s been a while since I’ve seen fares this good, and I don’t know how long these fares are going to last, so definitely book quickly. Anybody able to book these amazing fares?

Editorial Note: Opinions, analyses, reviews or suggestions expressed on this site are those of the author’s alone, and have not been reviewed, approved or otherwise endorsed by any card issuer. For details on current offers visit the card issuer’s site.

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