$408+ Cheap flights from Madrid, Spain (MAD) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
MAD — CHI
May 1 — May 81
Round-trip
1 adult, Economy
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Find cheap flights from Madrid to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Madrid Barajas to Chicago are usually found in January or November, booked 8 days in advance, depart on a Thursday or Monday and return on a Wednesday
Cheap flight deals from Madrid to Chicago
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Best
Last-minute
One-way
Cheapest flights from Madrid to ChicagoExplore the most affordable flight options available from Madrid to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 1, 2026.
Explore the most affordable flight options available from Madrid to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 1, 2026.
This TAP AIR PORTUGAL deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1810:25 pm
MAD
- ORD
1 stop24h 35m
TAP AIR PORTUGAL
Sat 4/256:05 pm
ORD
- MAD
1 stop11h 35m
TAP AIR PORTUGAL
Deal found 3/29![TAP AIR PORTUGAL logo]()
$561
This eDestinos deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/221:35 pm
MAD
- ORD
Nonstop9h 25m
Iberia
Tue 4/2811:22 am
ORD
- MAD
1 stop11h 13m
Iberia
Deal found 3/30![Iberia logo]()
$564
This eDestinos deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:35 pm
MAD
- ORD
Nonstop9h 25m
Iberia
Sat 10/179:05 pm
ORD
- MAD
1 stop11h 45m
Iberia
Deal found 3/28![Iberia logo]()
$571
This Rumbo deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Rumbo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:05 pm
MAD
- ORD
1 stop26h 05m
ITA Airways
Thu 5/73:00 pm
ORD
- MAD
1 stop12h 45m
ITA Airways
Deal found 3/30![ITA Airways logo]()
$572
This eDestinos deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2210:40 am
MAD
- ORD
1 stop15h 35m
Aer Lingus
Tue 4/283:45 pm
ORD
- MAD
1 stop11h 10m
Aer Lingus
Deal found 3/29![Aer Lingus logo]()
$575
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:00 am
MAD
- MDW
2 stops18h 58m
Delta
Sat 5/91:59 pm
MDW
- MAD
2 stops14h 21m
Delta
Deal found 3/30![Delta logo]()
$632
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
MAD
- MDW
2 stops18h 58m
Delta
Tue 4/281:24 pm
MDW
- MAD
2 stops15h 51m
Delta
Deal found 3/30![Delta logo]()
$636
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:00 am
MAD
- MDW
2 stops19h 36m
Delta
Fri 5/87:13 pm
MDW
- MAD
2 stops14h 12m
Delta
Deal found 3/30![Delta logo]()
$637
This Expedia deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2812:45 pm
MAD
- MDW
1 stop16h 43m
KLM
Fri 5/81:22 pm
MDW
- MAD
2 stops13h 08m
KLM
Deal found 3/29![KLM logo]()
$640
This Virgin Atlantic deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Virgin Atlantic is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/112:45 pm
MAD
- MDW
1 stop16h 43m
Virgin Atlantic
Thu 5/71:22 pm
MDW
- MAD
2 stops13h 33m
Virgin Atlantic
Deal found 3/30![Virgin Atlantic logo]()
$641
This KLM deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2512:45 pm
MAD
- MDW
1 stop16h 43m
KLM
Sat 5/25:21 pm
MDW
- MAD
1 stop11h 54m
KLM
Deal found 3/28![KLM logo]()
$642
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1812:45 pm
MAD
- MDW
1 stop16h 43m
Delta
Sat 4/257:16 pm
MDW
- MAD
2 stops14h 09m
Delta
Deal found 3/30![Delta logo]()
$643
Best flights from Madrid to ChicagoDiscover carefully curated flight deals from Madrid to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 1, 2026.
Discover carefully curated flight deals from Madrid to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 1, 2026.
This United Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/168:20 am
MAD
- ORD
1 stop18h 35m
United Airlines
Sun 4/192:25 pm
ORD
- MAD
1 stop10h 40m
United Airlines
Deal found 3/30![United Airlines logo]()
$620
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:00 am
MAD
- ORD
1 stop15h 15m
Delta
Sat 6/67:00 am
ORD
- MAD
1 stop16h 20m
Delta
Deal found 3/30![Delta logo]()
$630
This Virgin Atlantic deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Virgin Atlantic is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2512:45 pm
MAD
- MDW
1 stop16h 43m
Virgin Atlantic
Sat 5/25:40 am
MDW
- MAD
1 stop23h 35m
Virgin Atlantic
Deal found 3/28![Virgin Atlantic logo]()
$642
This British Airways deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/161:35 pm
MAD
- ORD
Nonstop9h 25m
British Airways
Sun 4/1910:30 pm
ORD
- MAD
Nonstop8h 00m
British Airways
Deal found 3/31![British Airways logo]()
$652
This Finnair deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/121:50 pm
MAD
- ORD
1 stop12h 55m
Multiple Airlines
Sat 9/1910:35 pm
ORD
- MAD
1 stop12h 35m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$664
This United Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/295:55 am
MAD
- ORD
2 stops16h 00m
United Airlines
Wed 5/69:07 am
ORD
- MAD
2 stops14h 43m
United Airlines
Deal found 3/30![United Airlines logo]()
$628
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:00 am
MAD
- ORD
1 stop15h 15m
Delta
Mon 5/2510:25 am
ORD
- MAD
1 stop12h 55m
Delta
Deal found 3/30![Delta logo]()
$630
This Delta deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/610:25 am
MAD
- ORD
2 stops17h 15m
Delta
Sun 5/105:19 pm
ORD
- MAD
2 stops16h 26m
Delta
Deal found 3/27![Delta logo]()
$634
This United Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:55 am
MAD
- ORD
2 stops17h 52m
United Airlines
Fri 5/812:55 pm
ORD
- MAD
2 stops15h 55m
United Airlines
Deal found 3/29![United Airlines logo]()
$634
This Delta deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/126:00 am
MAD
- MDW
2 stops18h 54m
Delta
Tue 4/2110:41 am
MDW
- MAD
2 stops16h 14m
Delta
Deal found 3/27![Delta logo]()
$637
This United Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:25 am
MAD
- ORD
1 stop33h 35m
United Airlines
Mon 8/3112:57 pm
ORD
- MAD
1 stop12h 08m
United Airlines
Deal found 3/29![United Airlines logo]()
$641
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:00 am
MAD
- MDW
2 stops18h 58m
Delta
Wed 5/67:16 pm
MDW
- MAD
2 stops14h 09m
Delta
Deal found 3/30![Delta logo]()
$637
This KLM deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/159:50 am
MAD
- MDW
1 stop13h 25m
Multiple Airlines
Sun 7/261:49 pm
MDW
- MAD
2 stops14h 31m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$860
This Delta deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/146:00 am
MAD
- MDW
2 stops18h 58m
Delta
Tue 4/285:21 pm
MDW
- MAD
1 stop11h 54m
Delta
Deal found 3/27![Delta logo]()
$637
This Delta deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/112:20 pm
MAD
- ORD
2 stops15h 20m
Delta
Wed 5/65:04 pm
ORD
- MAD
2 stops16h 41m
Delta
Deal found 3/28![Delta logo]()
$640
This Delta deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:00 am
MAD
- MDW
2 stops18h 58m
Delta
Sat 5/25:21 pm
MDW
- MAD
1 stop11h 54m
Delta
Deal found 3/28![Delta logo]()
$643
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/112:45 pm
MAD
- MDW
1 stop16h 43m
Delta
Sat 5/91:59 pm
MDW
- MAD
2 stops14h 21m
Delta
Deal found 4/1![Delta logo]()
$661
This Delta deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:00 am
MAD
- ORD
2 stops19h 05m
Delta
Sat 6/1310:29 am
ORD
- MAD
1 stop12h 51m
Delta
Deal found 3/28![Delta logo]()
$677
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/310:25 am
MAD
- MDW
2 stops29h 18m
Delta
Sun 6/149:17 am
MDW
- MAD
2 stops17h 13m
Delta
Deal found 3/29![Delta logo]()
$678
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:00 am
MAD
- MDW
2 stops19h 31m
Delta
Sat 9/195:59 pm
MDW
- MAD
2 stops15h 26m
Delta
Deal found 4/1![Delta logo]()
$718
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:00 am
MAD
- MDW
2 stops19h 25m
Delta
Sun 7/269:20 am
MDW
- MAD
2 stops19h 00m
Delta
Deal found 3/31![Delta logo]()
$855
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/136:00 am
MAD
- MDW
2 stops19h 25m
Delta
Thu 7/309:20 am
MDW
- MAD
2 stops17h 35m
Delta
Deal found 3/31![Delta logo]()
$858
This Delta deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/49:50 am
MAD
- MDW
1 stop19h 27m
Delta
Sat 7/186:35 pm
MDW
- MAD
2 stops14h 50m
Delta
Deal found 3/27![Delta logo]()
$864
Last-minute flights from Madrid to ChicagoDiscover last-minute flight deals from Madrid to Chicago. Data last updated April 1, 2026 and is based on user searches.
Discover last-minute flight deals from Madrid to Chicago. Data last updated April 1, 2026 and is based on user searches.
This Flighttix deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flighttix is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/65:55 am
MAD
- ORD
1 stop14h 00m
Multiple Airlines
Sun 4/192:20 pm
ORD
- MAD
1 stop21h 20m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$620
This United Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/65:55 am
MAD
- ORD
1 stop14h 00m
United Airlines
Mon 4/1311:15 am
ORD
- MAD
2 stops14h 45m
United Airlines
Deal found 3/30![United Airlines logo]()
$621
This Lufthansa deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Lufthansa is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/65:55 am
MAD
- ORD
1 stop14h 00m
Multiple Airlines
Mon 4/137:05 pm
ORD
- MAD
1 stop16h 35m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$622
This lol.travel deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/91:35 pm
MAD
- ORD
Nonstop9h 25m
Finnair
Thu 4/2310:30 pm
ORD
- MAD
Nonstop8h 00m
Finnair
Deal found 3/31![Finnair logo]()
$602
This lol.travel deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/91:35 pm
MAD
- ORD
Nonstop9h 25m
Finnair
Wed 4/2210:30 pm
ORD
- MAD
Nonstop8h 00m
Finnair
Deal found 3/28![Finnair logo]()
$604
This lastminute.com deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/91:35 pm
MAD
- ORD
Nonstop9h 25m
British Airways
Wed 4/2210:30 pm
ORD
- MAD
Nonstop8h 00m
British Airways
Deal found 3/27![British Airways logo]()
$617
This Ticket deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Ticket is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/910:25 am
MAD
- ORD
1 stop12h 56m
British Airways
Thu 4/2311:15 am
ORD
- MAD
1 stop11h 15m
British Airways
Deal found 3/30![British Airways logo]()
$619
This Delta deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:00 am
MAD
- MDW
2 stops18h 58m
Delta
Sat 4/256:38 pm
MDW
- MAD
2 stops14h 47m
Delta
Deal found 3/28![Delta logo]()
$638
This Virgin Atlantic deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Virgin Atlantic is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2112:45 pm
MAD
- MDW
1 stop16h 43m
Virgin Atlantic
Mon 5/41:24 pm
MDW
- MAD
2 stops13h 31m
Virgin Atlantic
Deal found 3/30![Virgin Atlantic logo]()
$641
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
MAD
- MDW
2 stops18h 58m
Delta
Tue 4/285:21 pm
MDW
- MAD
1 stop11h 54m
Delta
Deal found 3/30![Delta logo]()
$636
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:00 am
MAD
- MDW
2 stops19h 36m
Delta
Fri 5/87:13 pm
MDW
- MAD
2 stops14h 12m
Delta
Deal found 3/30![Delta logo]()
$637
This Expedia deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2812:45 pm
MAD
- MDW
1 stop16h 43m
KLM
Fri 5/81:22 pm
MDW
- MAD
2 stops13h 08m
KLM
Deal found 3/29![KLM logo]()
$640
One-way flights from Madrid to ChicagoSearch for one-way flight options from Madrid to Chicago. Find affordable one-way fares based on user searches. Data last updated April 1, 2026.
Search for one-way flight options from Madrid to Chicago. Find affordable one-way fares based on user searches. Data last updated April 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/184:40 pm
MAD
- MDW
3 stops28h 32m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$408
This Mytrip deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/132:20 am
MAD
- ORD
2 stops27h 55m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$408
This Mytrip deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:20 pm
MAD
- ORD
3 stops30h 51m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$409
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/275:20 pm
MAD
- ORD
2 stops38h 04m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$410
This Kiwi.com deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:50 am
MAD
- ORD
2 stops19h 25m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$411
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/14:40 pm
MAD
- ORD
2 stops38h 44m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$412
This Mytrip deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/285:20 pm
MAD
- ORD
3 stops30h 51m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/134:40 pm
MAD
- MDW
3 stops57h 51m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:10 pm
MAD
- ORD
2 stops34h 15m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/410:40 am
MAD
- ORD
3 stops38h 10m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$415
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1411:05 am
MAD
- MDW
3 stops32h 55m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$416
This Kiwi.com deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/184:40 pm
MAD
- ORD
2 stops49h 39m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$416
Find flight deals from Madrid to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Madrid (MAD) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $561 (TAP AIR PORTUGAL) |
One-way from | $408 (Kiwi.com) |
Popular in | August |
Cheapest in | January |
Average price | $631 |
Good round-trip deal | $890 or less |
Good one-way deal | $521 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Madrid to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 1, 2026.
Use the filters below to find and compare flights from Madrid to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MadridChicago
MAD - ORD
MADORD
Madrid Barajas
Thu 4/16
8:20 am-7:55 pm
1 stop18h 35m
Chicago O'Hare Intl
Sun 4/19
2:25 pm-8:05 am
1 stop10h 40m
$620
MadridChicago
MAD - ORD
MADORD
Madrid Barajas
Wed 4/29
5:55 am-2:55 pm
2 stops16h 00m
Chicago O'Hare Intl
Wed 5/6
9:07 am-6:50 am
2 stops14h 43m
$628
MadridChicago
MAD - ORD
MADORD
Madrid Barajas
Fri 4/17
6:00 am-2:15 pm
1 stop15h 15m
Chicago O'Hare Intl
Sat 6/6
7:00 am-6:20 am
1 stop16h 20m
$630
MadridChicago
MAD - ORD
MADORD
Madrid Barajas
Tue 5/19
6:00 am-2:15 pm
1 stop15h 15m
Chicago O'Hare Intl
Mon 5/25
10:25 am-6:20 am
1 stop12h 55m
$630
MadridChicago
MAD - ORD
MADORD
Madrid Barajas
Wed 5/6
10:25 am-8:40 pm
2 stops17h 15m
Chicago O'Hare Intl
Sun 5/10
5:19 pm-4:45 pm
2 stops16h 26m
$634
MadridChicago
MAD - ORD
MADORD
Madrid Barajas
Sat 5/2
5:55 am-4:47 pm
2 stops17h 52m
Chicago O'Hare Intl
Fri 5/8
12:55 pm-11:50 am
2 stops15h 55m
$634
MadridChicago
MAD - MDW
MADMDW
Madrid Barajas
Sun 4/12
6:00 am-5:54 pm
2 stops18h 54m
Chicago Midway
Tue 4/21
10:41 am-9:55 am
2 stops16h 14m
$637
MadridChicago
MAD - MDW
MADMDW
Madrid Barajas
Wed 4/29
6:00 am-5:58 pm
2 stops18h 58m
Chicago Midway
Wed 5/6
7:16 pm-4:25 pm
2 stops14h 09m
$637
MadridChicago
MAD - MDW
MADMDW
Madrid Barajas
Tue 4/14
6:00 am-5:58 pm
2 stops18h 58m
Chicago Midway
Tue 4/28
5:21 pm-12:15 pm
1 stop11h 54m
$637
MadridChicago
MAD - ORD
MADORD
Madrid Barajas
Fri 5/1
12:20 pm-8:40 pm
2 stops15h 20m
Chicago O'Hare Intl
Wed 5/6
5:04 pm-4:45 pm
2 stops16h 41m
$640
Showing 1-10 of 41 resultsSorted by cheapest first
Compare providers for flights from Madrid to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Madrid to Chicago in April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Madrid-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madrid-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madrid-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Madrid-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Madrid-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Madrid to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Madrid with our price prediction graph.
MAD-CHI
MAD-ORD
MAD-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Madrid to Chicago
MAD-CHI
MAD-ORD
MAD-MDW
How far ahead should I book a flight from Madrid to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Madrid to Chicago. Price data was last updated on March 13, 2026.
To ensure you get the cheapest price possible for a flight from Madrid to Chicago, you should look to book at least 8 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Madrid to Chicago?
Currently, February is the cheapest month in which you can book a flight from Madrid to Chicago (average of $430). Flying from Madrid to Chicago in July is currently the most expensive (average of $620). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MAD to CHI?
Find hourly flight availability from Madrid to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 1, 2026.
When flying from Madrid to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Madrid to Chicago
Explore weekly flight availability from Madrid to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 1, 2026.
The most flights from MAD to CHI are scheduled on a Monday (10 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (4 on average).
How much does it cost to fly round-trip from Madrid to Chicago?
How often are flights from Madrid to Chicago delayed?
About 15% of weekly flights between Madrid and Chicago have experienced delays in the past year, with the average delay time being 173 minutes.
What is the most punctual flight time for Madrid to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Madrid to Chicago flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 12% of flights being delayed.
The best insider tips for Madrid to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Madrid to Chicago trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated April 1, 2026.
See what other customers who have flown with Finnair,American Airlines, andTAP AIR PORTUGAL from Madrid to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.7
Comfort
7.5
Entertainment
6.9
Overall
7.7
Crew
8.2
Boarding
7.7
Reviews
1 / 20
4.0
OkayAnonymous,Sep 2025
WAW - HEL
Food
6.7
Comfort
7.5
Entertainment
6.9
Overall
7.7
Crew
8.2
Boarding
7.7
Reviews
1 / 20
4.0
OkayAnonymous,Sep 2025
WAW - HEL
Food
6.7
Comfort
7.5
Entertainment
6.9
Overall
7.7
Crew
8.2
Boarding
7.7
Reviews
1 / 20
4.0
OkayAnonymous,Sep 2025
WAW - HEL
Food
6.7
Comfort
7.5
Entertainment
6.9
Overall
7.7
Crew
8.2
Boarding
7.7
Reviews
1 / 20
4.0
OkayAnonymous,Sep 2025
WAW - HEL
Food
6.7
Comfort
7.5
Entertainment
6.9
Overall
7.7
Crew
8.2
Boarding
7.7
Reviews
1 / 20
4.0
OkayAnonymous,Sep 2025
WAW - HEL
Food
6.7
Comfort
7.5
Entertainment
6.9
Overall
7.7
Crew
8.2
Boarding
7.7
Reviews
1 / 20
4.0
OkayAnonymous,Sep 2025
WAW - HEL
Related info for your journey
Find useful and relevant information for your journey from Madrid to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on April 1, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Madrid to Chicago by cabin class
Find flights from Madrid to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Madrid and Chicago flights
Browse other Madrid and Chicago flight options. Last updated on April 1, 2026.
Other flights from Madrid
Browse through other flights departing from Madrid. Flights are based on user searches made on Cheapflights and were last updated on April 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Madrid to Chicago
Discover the top 3 airlines that operate flights from Madrid to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$501 | Average$815 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$534 | Average$674 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$542 | Average$869 | FlexibilityNo cancel fee | On-time70% |