AirHint found the following cheapest return flights from Chicago (ORD) to Madrid (MAD) in January 2026 (see full year).

Return flights

14 Jan - 23 Jan	TAP
23 Jan - 30 Jan	TAP
23 Jan - 28 Jan	TAP
16 Jan - 23 Jan	TAP
16 Jan - 21 Jan	TAP
14 Jan - 21 Jan	TAP
23 Jan - 27 Jan	TAP
28 Jan - 04 Feb	TAP
30 Jan - 06 Feb	TAP
30 Jan - 04 Feb	TAP
28 Jan - 06 Feb	TAP
09 Jan - 16 Jan	TAP
18 Jan - 31 Jan	TAP
02 Jan - 09 Jan	TAP
30 Jan - 06 Feb	British Airways	direct
31 Jan - 05 Feb	Aer Lingus
31 Jan - 05 Feb	British Airways	direct

Also check the deals for one-way flights from Chicago to Madrid in January.

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

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Cheapest return flights from Chicago to Madrid in January from 254€

Return flights