Image Credits: Dimitry B, Creative Commons 2.0 (flickr)
Published February 15, 2020 by

Cheap Flights: Chicago to/from Madrid $355-$415 r/t – Iberia / American / British Airways

[12/20/2019 @ 12:12 PM CT] Book this fare on: Google Flights, Priceline, BookingBuddy, Travelocity, SkyScanner, Expedia, Orbitz, Hotwire, CheapTickets.

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

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Iberia, American, and British Airways have round-trip flights from Chicago (ORD) to Madrid (MAD) for $355-$415, NONSTOP or with a connection. Flights March, October, November, and December. Most nonstop flights are after October.

Note: Carry-on bag is allowed for free. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

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  • All Example Dates (Google Flights): Mar 16 – Mar 25 / Mar 17 – Mar 24 / Mar 17 – Mar 26 / Mar 18 – Mar 25 / Mar 23 – Apr 01 / Mar 24 – Mar 31 / Mar 25 – Apr 01 / Mar 29 – Apr 07 / Mar 30 – Apr 06 / Mar 30 – Apr 08 / Mar 31 – Apr 07 / Oct 04 – Oct 13 / Oct 05 – Oct 14 / Oct 06 – Oct 13 / Oct 06 – Oct 15 / Oct 07 – Oct 14 / Oct 07 – Oct 16 / Oct 11 – Oct 20 / Oct 13 – Oct 20 / Oct 13 – Oct 22 / Oct 14 – Oct 21 / Oct 14 – Oct 23 / Oct 18 – Oct 27 / Oct 19 – Oct 28 / Oct 20 – Oct 27 / Oct 20 – Oct 29 / Oct 21 – Oct 28 / Oct 21 – Oct 30 / Oct 25 – Nov 01 / Oct 25 – Nov 03 / Oct 26 – Nov 02 / Oct 26 – Nov 04 / Oct 27 – Nov 03 / Oct 27 – Nov 05 / Oct 28 – Nov 04 / Oct 28 – Nov 06 / Oct 29 – Nov 05 / Oct 30 – Nov 06 / Nov 01 – Nov 08 / Nov 01 – Nov 10 / Nov 02 – Nov 09 / Nov 02 – Nov 11 / Nov 03 – Nov 12 / Nov 04 – Nov 11 / Nov 04 – Nov 13 / Nov 05 – Nov 12 / Nov 06 – Nov 13 / Nov 08 – Nov 15 / Nov 08 – Nov 17 / Nov 09 – Nov 16 / Nov 09 – Nov 18 / Nov 10 – Nov 17 / Nov 10 – Nov 19 / Nov 11 – Nov 18 / Nov 11 – Nov 20 / Nov 12 – Nov 19 / Nov 13 – Nov 20 / Nov 15 – Nov 22 / Nov 15 – Nov 24 / Nov 16 – Nov 23 / Nov 16 – Nov 25 / Nov 17 – Nov 24 / Nov 17 – Nov 26 / Nov 18 – Nov 25 / Nov 18 – Nov 27 / Nov 22 – Dec 01 / Nov 23 – Dec 02 / Nov 24 – Dec 01 / Nov 24 – Dec 03 / Nov 25 – Dec 02 / Nov 25 – Dec 04 / Nov 26 – Dec 03 / Nov 27 – Dec 04 / Nov 29 – Dec 06 / Nov 29 – Dec 08 / Nov 30 – Dec 07 / Nov 30 – Dec 09 / Dec 01 – Dec 08 / Dec 02 – Dec 09 / Dec 02 – Dec 11 / Dec 03 – Dec 10 / Dec 04 – Dec 11 / Dec 06 – Dec 13 / Dec 06 – Dec 15 / Dec 07 – Dec 14 / Dec 07 – Dec 16 / Dec 08 – Dec 15 / Dec 08 – Dec 17 / Dec 09 – Dec 16 / Dec 09 – Dec 18 / Dec 10 – Dec 17 / Dec 13 – Dec 20 / Dec 13 – Dec 22 / Dec 14 – Dec 21 / Dec 14 – Dec 23 / Dec 15 – Dec 24 / 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 up on Google Flights. Screenshot taken when this post was initially created. See timestamps at the top of this post.

Flight Details:


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EXAM:ORD,MDW:MAD:TP,EI,DE*TP,EI,DE:1::e:9,7,5:1000:443:SP:avg470

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 Madrid Oneworld