Price live-checked 14 hours ago

Cheap flights from Madrid to Chicago

€563 return, one stop or more with TAP Air Portugal. Live-checked against real availability, with exact dates and price history.

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Madrid → Chicago

TAP Air Portugal

€563 RT

19% above usual

for 13 Mar – 24 Mar 2027

✓ live-checked 14 hours ago

Check live price on Skyscanner →

All sample dates each opens live Skyscanner prices for those exact dates

13 Mar – 24 Mar 2027 €563 cheapest

Is €563 a good price?

Not really. It is 19% above the usual €472, so waiting for a drop may pay off. The lowest we have seen is €367.

Now: €563
Usual price: €472
Lowest seen: €367
Highest seen: €590
Cheapest month: March 2027

Based on 95 price checks of this route.

Other deals to Chicago

Gdansk31 Jan – 15 Feb €360 Vilnius24 Nov – 6 Dec €442 London Gatwick5 Nov – 22 Nov £443 Riga19 Feb – 2 Mar €445

Other deals from Madrid

Sharm El Sheikh23 Feb – 2 Mar €152 Olbia11 Mar – 18 Mar €43 Anchorage1 Feb – 15 Feb €664 Puerto Plata16 Aug – 27 Aug €712

Madrid to Chicago flights: common questions

How much is a flight from Madrid to Chicago?

The lowest return fare we currently track from Madrid (MAD) to Chicago (ORD) is €563. That is above the typical €472 on this route. Over 95 recorded checks we have seen it as low as €367 and as high as €590.

Which airline flies from Madrid to Chicago at this price?

This €563 fare is with TAP Air Portugal, with at least one connection. The live search lists every carrier serving the route, so you can compare schedules before booking.

Is there a direct flight from Madrid to Chicago?

This €563 fare includes at least one connection. If you need a non-stop Madrid to Chicago flight, open the live search and apply the direct filter there.

When is the cheapest time to fly from Madrid to Chicago?

Our price sampling points to March 2027 as the cheapest departure month on this route. The dated links on this page cover March 2027.

Is the €563 Madrid to Chicago fare still available?

We last confirmed this €563 fare against live Skyscanner availability 14 hours ago. Deal fares move within days, so the Check live price button re-runs the exact search and shows today's number rather than a cached one.

How do I book this Madrid to Chicago deal?

Pick a date pair above or press Check live price. That opens the exact MAD–ORD search on Skyscanner, where you book directly with the airline or agent. TravelFree does not sell tickets, adds no booking fee and does not mark the price up.

Every Madrid to Chicago price on this page comes from a real bookable quote and is re-checked automatically. TravelFree takes no commission from you and never marks a fare up.

About flights from Madrid to Chicago

The cheapest Madrid to Chicago return flight on the radar right now is €563, flying with TAP Air Portugal via one or more connections. It covers departures in March 2027, and every dated link below opens that exact MAD–ORD search on Skyscanner. The price we usually record on this route is €472. Across 95 recorded checks it has ranged between €367 and €590. Our sampling points to March 2027 as the cheapest month to fly Madrid to Chicago.

We do not post a price and leave it to age. Each fare is re-checked against Skyscanner on a schedule and carries the time it was last confirmed. Not flying from Madrid? We track 61 other departure cities for Chicago, listed at the foot of this page.

Cheap fares do not hang around. If this one has already gone, nudge the dates either way by a day or two; Madrid to Chicago is usually still decent value around the same window.

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