Cheap flights from Madrid to Chicago from €308

Cheapest one-way tickets

Recent finds on different dates, for 1 adult. Baggage and fare rules are shown on Aviasales, where the price is checked live.

Cheapest

€308

TAP Air Portugal, flight TP 1023Found 4 days ago, 1 adult

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07:40MadridWed, Nov 4

Travel time 11h 15m, 1 stopMADORD

11:55ChicagoWed, Nov 4

€309

TAP Air Portugal, flight TP 1017Found 4 days ago, 1 adult

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18:00MadridThu, Nov 5

Travel time 11h, 1 stopMADORD

22:00ChicagoThu, Nov 5

€329

TAP Air Portugal, flight TP 1017Found 6 days ago, 1 adult

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18:00MadridTue, Nov 3

Travel time 11h 15m, 1 stopMADORD

22:15ChicagoTue, Nov 3

€329

Portugalia Airlines, flight NI 1021Found 2 days ago, 1 adult

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21:10MadridThu, Jan 28

Travel time 11h, 1 stopMADORD

01:10ChicagoFri, Jan 29

€329

TAP Air Portugal, flight TP 1023Found 2 days ago, 1 adult

Check price on Aviasales

07:40MadridFri, Jan 29

Travel time 11h, 1 stopMADORD

11:40ChicagoFri, Jan 29

Round trips

The cheapest return tickets found recently, price for the whole trip.

Plan the rest of the trip

Mobile data in United StatesTravel eSIM from $4, installed before you fly.
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Getting from the airportTransfers and car hire in Chicago, booked ahead at a fixed price.
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Things to do in ChicagoPopular tours from $27.95 per person.
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Flight delayed?Arrived 3+ hours late, cancelled at short notice or bumped? Up to €600 per person under EU261.
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Price calendar

The lowest one-way fare found for each day over the next 60 days. A dash means no recent fare; you can still pick that day.

October 2026

MoTuWeThFrSaSu1234–5€617 6–7–8–9–10–11–12€594 13–14–15–16–17€553 18€695 19–20–21–22–23–24–25–26–27–28–29–30–31–

November 2026

MoTuWeThFrSaSu1–2–3€329 4€308 5€309 6–7–8–9–10–11–12–13–14–15–16–17–18–19–20–21–22–23–24–25–26–27–28–29–30–

December 2026

MoTuWeThFrSaSu1–2–345678910111213141516171819202122232425262728293031

€309 or lessGreen: the cheapest fifth of fares on this route. Lowest in these 60 days: Nov 4, €308.

Lowest fares by month

In the fares found this week, November has the lowest: from €308 one-way, against €553 in October. Pick a month to see its cheapest date.

Show as a table

Month	Cheapest one-way	Date	Stops
October	€553	Sat, Oct 17	2 stops
November	€308	Wed, Nov 4	1 stop
December	—
January 2027	€329	Thu, Jan 28	1 stop
February 2027	—
March 2027	—
April 2027	—
May 2027	—
June 2027	—
July 2027	—
August 2027	—
September 2027	—

Questions travellers ask

What is the cheapest month to fly from Madrid to Chicago?

In the fares found this week, November has the lowest: from €308 one-way, against €553 in October.

Are there direct flights from Madrid to Chicago?

None of the fares found recently are nonstop. The cheapest options have at least one stop.

More cheap flights from Madrid

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