$428+ Cheap flights from Madrid, Spain (MAD) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
MAD — CHI
Nov 24 — Dec 11
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 February or January, booked 40 days in advance, depart on a Thursday or Tuesday 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 October 25, 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 October 25, 2026.
This Gotogate deal was found by Cheapflights users on 10/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:00 pm -
1 stop28h 30m
Wed 11/257:00 pm -
1 stop18h 20m
Deal found 10/20![TAP AIR PORTUGAL logo]()
$547
This Booking.com deal was found by Cheapflights users on 10/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/512:10 pm -
1 stop34h 20m
Wed 2/37:00 pm -
1 stop12h 05m
Deal found 10/22![TAP AIR PORTUGAL logo]()
$549
This Gotogate deal was found by Cheapflights users on 10/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:00 pm -
1 stop28h 30m
Sun 11/158:10 pm -
1 stop17h 10m
Deal found 10/20![TAP AIR PORTUGAL logo]()
$551
This Cheapflightsfares deal was found by Cheapflights users on 10/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:40 am -
1 stop14h 50m
Wed 11/257:00 pm -
1 stop12h 05m
Deal found 10/21![TAP AIR PORTUGAL logo]()
$554
This Kissandfly.com deal was found by Cheapflights users on 10/22. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/199:10 pm -
1 stop25h 20m
Fri 1/158:10 pm -
1 stop20h 20m
Deal found 10/22![TAP AIR PORTUGAL logo]()
$566
This Kiwi.com deal was found by Cheapflights users on 10/22. 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.
Wed 11/47:40 am -
1 stop14h 50m
Fri 11/138:10 pm -
1 stop20h 20m
Deal found 10/22![TAP AIR PORTUGAL logo]()
$568
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/39:10 pm -
1 stop25h 20m
Fri 11/138:10 pm -
1 stop10h 55m
Deal found 10/22![TAP AIR PORTUGAL logo]()
$569
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Wed 11/47:40 am -
1 stop14h 50m
Wed 1/277:00 pm -
1 stop12h 05m
Deal found 10/21![TAP AIR PORTUGAL logo]()
$570
This Trip.com deal was found by Cheapflights users on 10/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:55 pm -
1 stop31h 35m
Sun 1/318:10 pm -
1 stop17h 10m
Deal found 10/22![TAP AIR PORTUGAL logo]()
$571
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Wed 11/47:40 am -
1 stop14h 50m
Fri 1/298:10 pm -
1 stop10h 55m
Deal found 10/21![TAP AIR PORTUGAL logo]()
$572
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/39:10 pm -
1 stop25h 20m
Sun 11/88:10 pm -
1 stop30h 20m
Deal found 10/21![TAP AIR PORTUGAL logo]()
$573
This Delta deal was found by Cheapflights users on 10/24. 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 12/16:05 am -
2 stops18h 56m
Sat 1/231:41 pm -
2 stops14h 49m
Deal found 10/24![Delta logo]()
$685
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 October 25, 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 October 25, 2026.
This Mytrip deal was found by Cheapflights users on 10/24. 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.
Thu 11/127:05 pm -
2 stops27h 25m
Wed 11/257:00 pm -
1 stop15h 10m
Deal found 10/24![Multiple Airlines logo]()
$637
This British Airways deal was found by Cheapflights users on 10/23. 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 1/2110:40 am -
1 stop15h 35m
Mon 1/255:10 pm -
1 stop11h 45m
Deal found 10/23![British Airways logo]()
$651
This Delta deal was found by Cheapflights users on 10/23. 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.
Thu 1/146:05 am -
1 stop15h 20m
Wed 1/2010:30 am -
2 stops18h 00m
Deal found 10/23![Delta logo]()
$653
This Scandinavian Airlines deal was found by Cheapflights users on 10/23. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2312:30 pm -
2 stops35h 15m
Mon 12/287:10 pm -
2 stops32h 55m
Deal found 10/23![Scandinavian Airlines logo]()
$693
This Delta deal was found by Cheapflights users on 10/24. 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 2/236:05 am -
2 stops17h 32m
Sun 2/286:25 pm -
1 stop17h 45m
Deal found 10/24![Delta logo]()
$657
This British Airways deal was found by Cheapflights users on 10/21. 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.
Wed 11/412:40 pm -
Nonstop9h 25m
Wed 1/275:10 pm -
1 stop18h 25m
Deal found 10/21![British Airways logo]()
$665
This Finnair deal was found by Cheapflights users on 10/22. 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.
Mon 11/1612:00 pm -
Nonstop9h 55m
Mon 11/306:30 pm -
1 stop13h 20m
Deal found 10/22![Multiple Airlines logo]()
$692
This Delta deal was found by Cheapflights users on 10/23. 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.
Thu 1/146:05 am -
2 stops19h 32m
Wed 1/201:00 pm -
2 stops15h 30m
Deal found 10/23![Delta logo]()
$658
This British Airways deal was found by Cheapflights users on 10/21. 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.
Wed 11/412:40 pm -
Nonstop9h 25m
Tue 1/264:00 pm -
2 stops18h 05m
Deal found 10/21![British Airways logo]()
$665
This Delta deal was found by Cheapflights users on 10/20. 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.
Thu 12/1712:20 pm -
1 stop17h 34m
Sun 1/109:30 am -
2 stops17h 25m
Deal found 10/20![Delta logo]()
$685
This Delta deal was found by Cheapflights users on 10/24. 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 12/16:05 am -
2 stops18h 56m
Sat 1/231:41 pm -
2 stops14h 49m
Deal found 10/24![Delta logo]()
$685
This Delta deal was found by Cheapflights users on 10/24. 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.
Thu 12/176:05 am -
2 stops17h 12m
Sun 1/106:00 pm -
2 stops16h 45m
Deal found 10/24![Delta logo]()
$685
This Delta deal was found by Cheapflights users on 10/20. 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.
Thu 11/126:05 am -
2 stops18h 59m
Wed 11/251:05 pm -
1 stop13h 40m
Deal found 10/20![Delta logo]()
$706
This Delta deal was found by Cheapflights users on 10/21. 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 11/149:20 am -
2 stops20h 34m
Sun 11/2210:34 am -
2 stops13h 46m
Deal found 10/21![Delta logo]()
$712
This Delta deal was found by Cheapflights users on 10/24. 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 11/86:05 am -
2 stops18h 55m
Tue 11/171:31 pm -
2 stops14h 59m
Deal found 10/24![Delta logo]()
$713
This Delta deal was found by Cheapflights users on 10/24. 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 11/1812:20 pm -
1 stop17h 34m
Wed 11/251:31 pm -
2 stops14h 59m
Deal found 10/24![Delta logo]()
$718
Last-minute flights from Madrid to ChicagoDiscover last-minute flight deals from Madrid to Chicago. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Madrid to Chicago. Data last updated October 25, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/39:10 pm -
1 stop25h 20m
Fri 11/138:10 pm -
1 stop10h 55m
Deal found 10/22![TAP AIR PORTUGAL logo]()
$569
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/39:10 pm -
1 stop25h 20m
Sun 11/88:10 pm -
1 stop30h 20m
Deal found 10/21![TAP AIR PORTUGAL logo]()
$573
This Kiwi.com deal was found by Cheapflights users on 10/22. 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.
Wed 11/47:40 am -
1 stop14h 50m
Fri 11/138:10 pm -
1 stop20h 20m
Deal found 10/22![TAP AIR PORTUGAL logo]()
$568
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Wed 11/47:40 am -
1 stop14h 50m
Wed 1/277:00 pm -
1 stop12h 05m
Deal found 10/21![TAP AIR PORTUGAL logo]()
$570
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Wed 11/47:40 am -
1 stop14h 50m
Fri 1/298:10 pm -
1 stop10h 55m
Deal found 10/21![TAP AIR PORTUGAL logo]()
$572
This Kiwi.com deal was found by Cheapflights users on 10/22. 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.
Wed 11/47:40 am -
1 stop14h 50m
Sun 11/228:10 pm -
1 stop14h 00m
Deal found 10/22![TAP AIR PORTUGAL logo]()
$574
This Booking.com deal was found by Cheapflights users on 10/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/512:10 pm -
1 stop34h 20m
Wed 2/37:00 pm -
1 stop12h 05m
Deal found 10/22![TAP AIR PORTUGAL logo]()
$549
This Trip.com deal was found by Cheapflights users on 10/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:55 pm -
1 stop31h 35m
Sun 1/318:10 pm -
1 stop17h 10m
Deal found 10/22![TAP AIR PORTUGAL logo]()
$571
This Delta deal was found by Cheapflights users on 10/22. 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.
Thu 11/56:05 am -
2 stops18h 55m
Sun 1/315:59 pm -
2 stops14h 21m
Deal found 10/22![Delta logo]()
$687
This Gotogate deal was found by Cheapflights users on 10/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:00 pm -
1 stop28h 30m
Wed 11/257:00 pm -
1 stop18h 20m
Deal found 10/20![TAP AIR PORTUGAL logo]()
$547
This Gotogate deal was found by Cheapflights users on 10/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:00 pm -
1 stop28h 30m
Sun 11/158:10 pm -
1 stop17h 10m
Deal found 10/20![TAP AIR PORTUGAL logo]()
$551
This Cheapflightsfares deal was found by Cheapflights users on 10/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:40 am -
1 stop14h 50m
Wed 11/257:00 pm -
1 stop12h 05m
Deal found 10/21![TAP AIR PORTUGAL logo]()
$554
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 October 25, 2026.
Search for one-way flight options from Madrid to Chicago. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This Finnair deal was found by Cheapflights users on 10/21. 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.
Sun 2/2112:00 pm -
Nonstop9h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Finnair logo]()
$428
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Sun 12/279:40 pm -
3 stops26h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Multiple Airlines logo]()
$429
This Kiwi.com deal was found by Cheapflights users on 10/22. 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.
Wed 12/27:40 pm -
2 stops50h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$430
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/36:30 am -
2 stops40h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Multiple Airlines logo]()
$431
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/110:30 am -
2 stops36h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$432
This Delta deal was found by Cheapflights users on 10/24. 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 1/206:05 am -
2 stops17h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Delta logo]()
$433
This Delta deal was found by Cheapflights users on 10/24. 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 3/96:05 am -
2 stops19h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Delta logo]()
$433
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 1/58:00 pm -
3 stops52h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Multiple Airlines logo]()
$435
This Delta deal was found by Cheapflights users on 10/21. 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 2/216:05 am -
2 stops21h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$436
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/97:05 pm -
2 stops51h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$437
This Virgin Atlantic deal was found by Cheapflights users on 10/24. 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 1/261:55 pm -
1 stop17h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Virgin Atlantic logo]()
$438
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 1/2512:00 pm -
Nonstop9h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Iberia logo]()
$438
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 October 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $547 (Gotogate) |
One-way from | $428 (Finnair) |
Popular in | August |
Cheapest in | February |
Average price | $637 |
Good round-trip deal | $753 or less |
Good one-way deal | $599 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 7,457,451 searches. Data last updated October 25, 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
Quickest round-trip
MadridChicago
MAD Madrid Barajas - ORD Chicago O'Hare Intl
MADORD
Madrid Barajas
Sun 2/21
12:00 pm-2:55 pm
Nonstop9h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$428
MadridChicago
MAD Madrid Barajas - MDW Chicago Midway
MADMDW
Madrid Barajas
Tue 1/26
6:05 am-6:00 pm
2 stops18h 55m
Chicago Midway
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$433
MadridChicago
MAD Madrid Barajas - MDW Chicago Midway
MADMDW
Madrid Barajas
Mon 1/18
6:05 am-6:37 pm
2 stops19h 32m
Chicago Midway
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$434
MadridChicago
MAD Madrid Barajas - MDW Chicago Midway
MADMDW
Madrid Barajas
Mon 2/8
6:05 am-6:37 pm
2 stops19h 32m
Chicago Midway
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$434
MadridChicago
MAD Madrid Barajas - ORD Chicago O'Hare Intl
MADORD
Madrid Barajas
Sun 2/21
6:05 am-8:37 pm
2 stops21h 32m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$436
MadridChicago
MAD Madrid Barajas - ORD Chicago O'Hare Intl
MADORD
Madrid Barajas
Tue 12/1
8:00 pm-3:30 pm
3 stops26h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$443
MadridChicago
MAD Madrid Barajas - ORD Chicago O'Hare Intl
MADORD
Madrid Barajas
Fri 3/5
12:00 pm-2:55 pm
Nonstop9h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$453
MadridChicago
MAD Madrid Barajas - MDW Chicago Midway
MADMDW
Madrid Barajas
Fri 3/5
6:05 am-6:37 pm
2 stops19h 32m
Chicago Midway
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$457
MadridChicago
MAD Madrid Barajas - ORD Chicago O'Hare Intl
MADORD
Madrid Barajas
Sun 1/17
6:05 am-9:33 pm
2 stops22h 28m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$458
MadridChicago
MAD Madrid Barajas - ORD Chicago O'Hare Intl
MADORD
Madrid Barajas
Fri 4/23
6:00 am-6:40 pm
2 stops19h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$479
Showing 1-10 of 37 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 October.
| 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
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 $550). Flying from Madrid to Chicago in August is currently the most expensive (average of $883). 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 October 25, 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.
How much does it cost to fly round-trip from Madrid to Chicago?
Airfare is typical for this route at the moment.
Madrid to Chicago flights typically cost between $546 and $736 in November.The cheapest round-trip price found within the last 5 days was $547 on TAP AIR PORTUGAL (Nov 12-Nov 25).
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 175 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?
Wednesday 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 8% of flights being delayed.
How far ahead should I book a flight from Madrid to Chicago?
To ensure you get the cheapest price possible for a flight from Madrid to Chicago, you should look to book at least 38 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.
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 October 25, 2026.
See what other customers who have flown with Finnair,TAP AIR PORTUGAL, andAmerican Airlines 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.
Boarding
7.6
Crew
8.2
Food
6.7
Overall
7.6
Entertainment
6.9
Comfort
7.4
Reviews
1 / 20
10.0
ExcellentJake,Jun 2026
RNO - SEA
Boarding
7.6
Crew
8.2
Food
6.7
Overall
7.6
Entertainment
6.9
Comfort
7.4
Reviews
1 / 20
10.0
ExcellentJake,Jun 2026
RNO - SEA
Boarding
7.6
Crew
8.2
Food
6.7
Overall
7.6
Entertainment
6.9
Comfort
7.4
Reviews
1 / 20
10.0
ExcellentJake,Jun 2026
RNO - SEA
Boarding
7.6
Crew
8.2
Food
6.7
Overall
7.6
Entertainment
6.9
Comfort
7.4
Reviews
1 / 20
10.0
ExcellentJake,Jun 2026
RNO - SEA
Boarding
7.6
Crew
8.2
Food
6.7
Overall
7.6
Entertainment
6.9
Comfort
7.4
Reviews
1 / 20
10.0
ExcellentJake,Jun 2026
RNO - SEA
Boarding
7.6
Crew
8.2
Food
6.7
Overall
7.6
Entertainment
6.9
Comfort
7.4
Reviews
1 / 20
10.0
ExcellentJake,Jun 2026
RNO - SEA
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 locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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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 October 25, 2026.
Complete your trip
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Madrid and Chicago flights
Browse other Madrid and Chicago flight options. Last updated on October 25, 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 October 25, 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 7,457,451 searches. Data last updated October 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$448 | Average$614 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$514 | Average$687 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$559 | Average$915 | FlexibilityNo cancel fee | On-time77% |