Cheap flights from Chicago to Madrid from $443 MDW, ORD, RFD → MAD
Chicago Midway International Airport (MDW), O'Hare International Airport (ORD), Chicago Rockford International Airport (RFD) → Adolfo Suarez Madrid-Barajas Airport (MAD)
The cheapest return found recently is $1,012 with TAP Air Portugal, 4 Jun 2027 – 7 Jun 2027, found 2 days ago. The cheapest one-way found recently is $443 with Virgin Atlantic, 4 Feb 2027, found 5 days ago.
- Cheapest one-way found recently
- $443, found 5 days ago
- Cheapest return found recently
- $1,012, 4 Jun 2027 to 7 Jun 2027
- Usual return price
- $1,335 to $1,695
- Cheapest month to fly
- December 2026, return fares from $901 found in the last 7 days
Return
The cheapest return fare on each of 9 departure dates is usually $1,335 to $1,695.
Cheapest return found recently
$1,012
4 Jun 2027 – 7 Jun 2027 · TAP Air Portugal
O'Hare International Airport (ORD) → Adolfo Suarez Madrid-Barajas Airport (MAD)
Leaves 5:45 p.m. · Return leaves 8:30 p.m. · 42 h 55 min of travel, both ways together
out 1 stop, back 1 stop
found 2 days ago
Cheapest nonstop return
None seen yet.
Found recently, and the cheapest we hold
$1,012 4 Jun 2027 – 7 Jun 2027found 2 days agoSee prices for these dates
$901 24 Dec – 26 Jan 2027found 7 days agoSee prices for these dates
What have prices looked like?
Over 46 days, 27 Sept to 11 Nov, the cheapest return we saw each day was $522 to $901.
At $1,012, the cheapest return found recently is above that range.
Those were the prices on those days, not today's.
Is this a good return price?
Compared with the cheapest return fare on each of 9 departure dates from 12 Dec to 4 Jun 2027, found by travelers' searches in the last 7 days (economy, the price the seller showed on Aviasales). The usual range is the middle half of those prices.
Could nearby dates be cheaper?
We hold no other 3-night return fares leaving within 3 days of 4 Jun 2027 to compare.
Every date we hold
17 fares on 9 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 12 Dec – 2 Jan 2027 | $1,523 | United Airlines | O'Hare International Airport (ORD) → Adolfo Suarez Madrid-Barajas Airport (MAD) | out 1 stop, back 2 stops | found 5 days ago | See prices for these dates |
| 13 Dec – 2 Jan 2027 | $1,476 | Aer Lingus | O'Hare International Airport (ORD) → Adolfo Suarez Madrid-Barajas Airport (MAD) | out 1 stop, back 2 stops | found 5 days ago | See prices for these dates |
| 14 Dec – 2 Jan 2027 | $1,335 | Icelandair | O'Hare International Airport (ORD) → Adolfo Suarez Madrid-Barajas Airport (MAD) | out 2 stops, back 2 stops | found 5 days ago | See prices for these dates |
| 15 Dec – 3 Jan 2027 | $1,516 | Air Canada | O'Hare International Airport (ORD) → Adolfo Suarez Madrid-Barajas Airport (MAD) | out 1 stop, back 1 stop | found 5 days ago | See prices for these dates |
| 17 Dec – 3 Jan 2027 | $1,695 | Air Canada | O'Hare International Airport (ORD) → Adolfo Suarez Madrid-Barajas Airport (MAD) | out 1 stop, back 1 stop | found 5 days ago | See prices for these dates |
| 18 Dec – 2 Jan 2027 | $1,913 | Icelandair | O'Hare International Airport (ORD) → Adolfo Suarez Madrid-Barajas Airport (MAD) | out 2 stops, back 3 stops | found 5 days ago | See prices for these dates |
| 20 Dec – 3 Jan 2027 | $1,860 | United Airlines | O'Hare International Airport (ORD) → Adolfo Suarez Madrid-Barajas Airport (MAD) | out 2 stops, back 2 stops | found 5 days ago | See prices for these dates |
| 24 Dec – 26 Jan 2027 | $901 | Air Canada | O'Hare International Airport (ORD) → Adolfo Suarez Madrid-Barajas Airport (MAD) | out 1 stop, back 2 stops | found 7 days ago | See prices for these dates |
| 4 Jun 2027 – 7 Jun 2027 | $1,012 | TAP Air Portugal | O'Hare International Airport (ORD) → Adolfo Suarez Madrid-Barajas Airport (MAD) | out 1 stop, back 1 stop | found 2 days ago | See prices for these dates |
Which month looks cheapest?
December 2026 is the cheapest month — from $901.
Airlines on the cheapest dates: Air Canada, United Airlines, Icelandair, Aer Lingus, TAP Air Portugal.
One-way
Not enough comparable prices yet for a usual one-way price.
Cheapest one-way found recently
$443
4 Feb 2027 · Virgin Atlantic
Chicago Midway International Airport (MDW) → Adolfo Suarez Madrid-Barajas Airport (MAD)
Leaves 5:45 p.m. · 30 h 35 min trip
2 stops
found 5 days ago
Cheapest nonstop one-way
None seen yet.
Found recently, and the cheapest we hold
$443 4 Feb 2027found 5 days agoOpen this trip
It is also the cheapest one-way we hold, of any age.
What have prices looked like?
Over 41 days, 24 Sept to 11 Nov, the cheapest one-way we saw each day was $310 to $554.
Those were the prices on those days, not today's.
Is this a good one-way price?
Not enough comparable prices yet: we hold one-way fares on 1 departure date and need at least 3 to say what is usual.
Could nearby dates be cheaper?
We hold no other one-way fares leaving within 3 days of 4 Feb 2027 to compare.
Every date we hold
2 fares on 1 departure dates
See every date as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 4 Feb 2027 | $443 | Virgin Atlantic | Chicago Midway International Airport (MDW) → Adolfo Suarez Madrid-Barajas Airport (MAD) | 2 stops | found 5 days ago | Open this trip |
Airlines on the cheapest dates: Virgin Atlantic.
Premium cabin fares from Chicago to Madrid
We hold no premium economy, business or first-class fares for this route: we collect them for the busiest routes, and this one is not among them yet.
Today's prices for 4 Jun 2027 – 7 Jun 2027 in another cabin: Premium economy · Business · First
Today's prices for 4 Feb 2027 in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Chicago to Madrid?
Return
Fares 30 to 59 days before departure were typically 40% lower than 0 to 6 days before departure.
From the cheapest return each day between 27 Sept and 11 Nov (46 days), grouped by how many days ahead the flight left; one adult in economy.
Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.
Prices reflect recent searches — current fares may differ.
See these ranges as a table
| Booked ahead by | Typical fare | Cheapest day | Above the cheapest | Days of prices |
|---|---|---|---|---|
| 0–6 days | $928 | $854 | +66% | 10 |
| 30–59 days | $559 | $522 | Cheapest seen | 25 |
| 60–89 days | $691 | $591 | +24% | 26 |
| 90–179 days | $609 | $574 | +9% | 42 |
| 180+ days | $618 | $615 | +11% | 13 |
One-way
Fares 60 to 89 days before departure were typically 8% lower than 30 to 59 days before departure.
From the cheapest one-way each day between 24 Sept and 11 Nov (41 days), grouped by how many days ahead the flight left; one adult in economy.
Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.
Prices reflect recent searches — current fares may differ.
See these ranges as a table
| Booked ahead by | Typical fare | Cheapest day | Above the cheapest | Days of prices |
|---|---|---|---|---|
| 30–59 days | $354 | $317 | +9% | 16 |
| 60–89 days | $326 | $310 | Cheapest seen | 23 |
| 90–179 days | $326 | $317 | +0% | 9 |
| 180+ days | $390 | $347 | +20% | 15 |
Live price for these dates
The cheapest return found recently is for 4 Jun 2027 – 7 Jun 2027. A live search on this page shows what those dates cost now, for one adult in economy.
Questions about this trip
How much is a return flight from Chicago to Madrid?
The cheapest return found recently is $1,012 with TAP Air Portugal, 4 Jun 2027 to 7 Jun 2027, found 2 days ago. The cheapest return we hold, of any age, is $901 with Air Canada, 24 Dec to 26 Jan 2027, found 7 days ago. The cheapest return fare on each of 9 departure dates is usually $1,335 to $1,695.
How much is a one-way flight from Chicago to Madrid?
The cheapest one-way found recently is $443 with Virgin Atlantic, 4 Feb 2027, found 5 days ago.
What is the cheapest month to fly from Chicago to Madrid?
December 2026 is the cheapest month for a return, from $901, 24 Dec to 26 Jan 2027, found 7 days ago.
How far ahead should I book a flight from Chicago to Madrid?
In 46 days of prices between 27 Sept and 11 Nov, return fares 30 to 59 days before departure were typically 40% lower than 0 to 6 days before departure. In 41 days of prices between 24 Sept and 11 Nov, one-way fares 60 to 89 days before departure were typically 8% lower than 30 to 59 days before departure.
How long is the flight from Chicago to Madrid?
The cheapest one-way found recently, with Virgin Atlantic on 4 Feb 2027, takes 30 h 35 min with 2 stops.
Which airlines have the cheapest flights from Chicago to Madrid?
Between 12 Dec and 4 Jun 2027, Air Canada has the cheapest return on 3 of the 9 departure dates we hold, United Airlines on 2 and Icelandair on 2.
Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work