Image Credits: Evangelio Gonzalez
Published November 17, 2017 by

Cheap Flights: Chicago to/from Key West $119 r/t – American

[11/17/2017 @ 10:39 AM CT] Book this fare on: Priceline, BookingBuddy, Travelocity, Orbitz, CheapTickets, Expedia, Hotwire.
[11/20/2017 @ 5:28 PM CT] 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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American Airlines has round-trip flights from Chicago (ORD) to Key West (EYW) for $119 with a connection. $59 each-way. Flights late-November to February. Origin/Destination reversible. Holiday blackouts apply.

Note: A great price for “Regular Economy”.

  • Example Dates: (Priceline / BookingBuddy) Nov 28 – Dec 01 / Dec 02 – Dec 06 / Dec 04 – Dec 08 / Dec 09 – Dec 14 / Dec 10 – Dec 16 / Dec 12 – Dec 19, 20, 25 / Blackout: Dec 15 – Jan 03 / Jan 04 – Jan 11 / Jan 13 – Jan 18, 19 / Jan 20 – Jan 24 / Jan 21 – Jan 25 / Jan 27 – Feb 01 / Jan 28 – Feb 02 / Feb 05- Feb 08 / Feb 11 – Feb 15 / Feb 18 – Feb 22 / Feb 25 – Mar 01 / Other dates: 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: The Chase Sapphire Preferred® Card allows for 1-to-1 point transfers to several airline loyalty programs. Booking with points is a good alternative to paying with cash when the price of airfare is high. Here is the current list of Chase Sapphire transfer partners: United, Southwest, jetBlue, British Airways, Iberia, Singapore Airlines, Emirates, Air France, KLM, Virgin Atlantic, Aer Lingus, and Air Canada.
  • 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.

I was able to pull this fare up on Priceline and Travelocity. Screenshot taken at 10:53 AM CT on 11/17/17.

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).

Airfare Deals American Airlines Flights from Chicago / Milwaukee Key West Oneworld