RareNonstop · 5h
CHI to SJUPuerto Rico
San Juan
$162
usually $340
−52%
Most monthly lows $287–$340. Cheaper than every other month on record (3).
Flights · CHI → MAD
Chicago to Madrid
Best fare, round trip
$574
−6%
below its usual $610
you keep $36
Found
- Depart
- Sun 21 Mar
- Return
- Thu 1 Apr
- Stay
- 11 nights
- Flight
- 1 stop · 9.5h
- Airline
TAP Air Portugal
Most of this route’s monthly lows fall between $608 and $720. The drop beats 8% of measured fares on the board, over 7 observed months.
Cached fare — the booking search re-prices live before you pay.
SpainMadridDinner at 10pm, museums at world-class density, and Iberia fare sales that border on typos.Best windowApr–Jun · Sep–OctAirportsBarajas (MAD)Every route into MadridFare seasonality
When this route gets cheap.
Fares bottom out in March around $574 and peak in December near $787, 37% dearer, across the 7 months we track. The cheapest itinerary we are tracking makes one stop and takes about 9.5 hours outbound, on a 11-night trip — ticketed under TAP Air Portugal, which on a connecting fare need not operate every leg. At $574 for 6,725 km each way, that works out to about $43 per 1,000 km flown. That is about the $44 per 1,000 km typical of long-haul fares here. Across the 12 departure cities we track at a similar distance from Madrid, this fare ranks 8th — 1.9× the $303 we hold from New York. That puts it in the cheaper half of the 28 routes of similar length we watch out of Chicago, where the middle fare is $729. The best time to be in Madrid: Apr–Jun · Sep–Oct.
The 5 days we hold a cached fare for
Press a date to compare its fares
The median cached fare across this calendar is 7% lower than when tracking began on 8 Aug — $750 then versus $700 now, across 13 recorded snapshots. This is a calendar-level trend, so an individual deal above can be lower. The lowest single day we have seen here is $574, on 21 Mar '27.
These are the only days we have a cached price for on this route so far — not the only days it flies. The search above covers any date.
Cached fares · checked 17 Oct 2026
Cheapest in Mar, around $574
6% below the $610 typical fare
$608Oct, around the usual price. Compare October fares.$787Dec, above the usual price. Compare December fares.$577Jan ’27, below the usual price. Compare January fares.$644Feb, above the usual price. Compare February fares.$574Mar, the cheapest month. Compare March fares.$610Apr, around the usual price. Compare April fares.$720May, above the usual price. Compare May fares.
CheapestBelow usualUsualAbove usualPress a month to compare its fares
Cheapest round-trip fare found each month, Chicago to Madrid, from cached prices.
Route facts
- Airports
- O’Hare (ORD) · Midway (MDW) ↔ Barajas (MAD)
- Flight time
- ≈9.5 hours outbound
- Distance
- ≈6,725 km each way
- Typical price
- $610 round-trip (seasonal median)
- Airlines on the board
- TAP Air Portugal
- Itineraries
- Connections on current fares
- Best months to visit
- Apr–Jun · Sep–Oct
Good to know
CHI → MAD, answered.
Is $574 a good price for Chicago to Madrid?
Only slightly. The seasonal median is around $610 round-trip and this fare is 6% under it. We do not call a drop notable until 20%, so this is an ordinary price for the route rather than a reason to hurry.
What is the cheapest month to fly from Chicago to Madrid?
Across 7 months of cached-fare history, Mar comes out cheapest on this route. The best months to actually be in Madrid are Apr–Jun · Sep–Oct — when those overlap, that's your window.
How far in advance should I book CHI → Madrid?
We do not publish a number for this, because we cannot measure it yet. Answering it honestly means watching the same departure date on this route over many weeks as it approaches, and that archive is still filling up — so any "book N days ahead" figure here would be borrowed from somewhere else rather than measured. What we can measure is which month is cheap: across 7 months of cached fares, Mar comes out lowest on this route. Our guide Why flight prices change covers what does move a fare.
Are there nonstop flights from Chicago to Madrid?
The current cheapest fares involve a connection, ticketed under TAP Air Portugal. We hold no nonstop fare on this route right now, which does not mean none flies — search your exact dates to see what does.
Are these prices guaranteed?
No — these are cached fares found on real searches (this one on 17 October). Airlines reprice constantly, so the booking search re-checks the live price before you pay. Fresher finds are far more likely to still be available.
Next step
Sleeping in Madrid?
Lock the flight first — then compare stays for 21 Mar '27 – 1 Apr '27 · 11 nights.
Browse hotelsMissed it?
Cached fares expire. This route has a feed of its own — follow it and the next CHI → MAD drop reaches you as soon as we find it.
Follow this route’s feedKeep browsing
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