$447+ 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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
MAD — CHI
Oct 7 — Oct 141
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 February, booked 64 days in advance, depart on a Thursday or Tuesday and return on a Wednesday
Cheap flight deals from Madrid to Chicago
Cheapest
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 September 7, 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 September 7, 2026.
This American Airlines deal was found by Cheapflights users on 9/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:00 pm -
Nonstop9h 55m
Mon 11/166:05 pm -
Nonstop8h 20m
Deal found 9/5![American Airlines logo]()
$560
This Air Canada deal was found by Cheapflights users on 9/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/171:25 pm -
2 stops17h 36m
Sun 1/101:55 pm -
2 stops14h 50m
Deal found 9/7![Multiple Airlines logo]()
$562
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/17:40 am -
1 stop12h 00m
Sat 10/36:05 pm -
1 stop11h 35m
Deal found 9/3![TAP AIR PORTUGAL logo]()
$563
This Expedia deal was found by Cheapflights users on 9/2. 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.
Sat 11/712:00 pm -
Nonstop9h 55m
Sun 11/157:05 pm -
1 stop31h 00m
Deal found 9/2![Iberia logo]()
$564
This Air Canada deal was found by Cheapflights users on 9/4. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/261:25 pm -
2 stops25h 32m
Thu 1/79:22 pm -
2 stops27h 38m
Deal found 9/4![Air Canada logo]()
$565
This Delta deal was found by Cheapflights users on 9/3. 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 12/146:05 am -
2 stops17h 45m
Sun 1/101:00 pm -
2 stops15h 30m
Deal found 9/3![Delta logo]()
$566
This Air Canada deal was found by Cheapflights users on 9/5. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/191:25 pm -
2 stops17h 36m
Wed 11/258:45 am -
2 stops16h 15m
Deal found 9/5![Air Canada logo]()
$566
This Delta deal was found by Cheapflights users on 9/7. 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 12/116:05 am -
2 stops18h 56m
Fri 1/291:00 pm -
2 stops15h 30m
Deal found 9/7![Delta logo]()
$568
This Expedia deal was found by Cheapflights users on 9/5. 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.
Fri 11/612:00 pm -
Nonstop9h 55m
Sun 11/158:30 pm -
1 stop13h 45m
Deal found 9/5![Iberia logo]()
$568
This Iberia deal was found by Cheapflights users on 9/3. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/212:40 pm -
Nonstop9h 25m
Thu 12/108:40 pm -
1 stop14h 50m
Deal found 9/3![Iberia logo]()
$569
This British Airways deal was found by Cheapflights users on 9/6. 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.
Fri 11/2012:40 pm -
Nonstop9h 30m
Fri 11/279:50 pm -
1 stop12h 15m
Deal found 9/6![British Airways logo]()
$570
This Delta deal was found by Cheapflights users on 9/3. 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 12/179:20 am -
2 stops20h 35m
Sun 1/105:59 pm -
2 stops14h 21m
Deal found 9/3![Delta logo]()
$572
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 September 7, 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 September 7, 2026.
This Delta deal was found by Cheapflights users on 9/6. 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 12/146:05 am -
2 stops17h 45m
Sun 1/101:00 pm -
2 stops15h 30m
Deal found 9/6![Delta logo]()
$568
This KLM deal was found by Cheapflights users on 9/7. 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 12/1212:20 pm -
1 stop17h 35m
Sat 1/301:00 pm -
2 stops15h 30m
Deal found 9/7![Multiple Airlines logo]()
$582
This SWISS deal was found by Cheapflights users on 9/5. 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 SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/207:30 pm -
2 stops23h 40m
Fri 11/275:45 pm -
2 stops18h 00m
Deal found 9/5![SWISS logo]()
$582
This United Airlines deal was found by Cheapflights users on 9/7. 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 12/196:05 am -
1 stop16h 15m
Mon 1/119:00 am -
2 stops17h 15m
Deal found 9/7![United Airlines logo]()
$583
This KLM deal was found by Cheapflights users on 9/7. 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.
Thu 12/1012:20 pm -
1 stop17h 35m
Thu 1/281:00 pm -
2 stops13h 55m
Deal found 9/7![KLM logo]()
$587
This British Airways deal was found by Cheapflights users on 9/6. 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 9/231:00 pm -
1 stop13h 38m
Wed 12/95:10 pm -
1 stop12h 05m
Deal found 9/6![British Airways logo]()
$639
This Virgin Atlantic deal was found by Cheapflights users on 9/2. 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.
Thu 2/111:55 pm -
1 stop15h 15m
Tue 2/166:00 am -
1 stop20h 45m
Deal found 9/2![Virgin Atlantic logo]()
$663
This Scandinavian Airlines deal was found by Cheapflights users on 9/2. 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.
Mon 11/25:00 pm -
2 stops35h 43m
Mon 11/167:15 pm -
2 stops32h 50m
Deal found 9/2![Scandinavian Airlines logo]()
$676
This Delta deal was found by Cheapflights users on 9/5. 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 12/116:05 am -
2 stops17h 45m
Wed 1/2012:30 pm -
2 stops16h 00m
Deal found 9/5![Delta logo]()
$568
This United Airlines deal was found by Cheapflights users on 9/6. 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 12/511:00 am -
2 stops17h 47m
Sun 12/1310:55 am -
2 stops15h 20m
Deal found 9/6![United Airlines logo]()
$594
This Delta deal was found by Cheapflights users on 9/3. 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 35m
Sun 1/105:59 pm -
2 stops18h 11m
Deal found 9/3![Delta logo]()
$572
This KLM deal was found by Cheapflights users on 9/5. 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.
Fri 9/186:00 am -
1 stop15h 15m
Mon 9/215:10 pm -
1 stop11h 10m
Deal found 9/5![Multiple Airlines logo]()
$707
This Delta deal was found by Cheapflights users on 9/6. 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 11/156:00 am -
2 stops18h 20m
Deal found 9/6![Delta logo]()
$600
This United Airlines deal was found by Cheapflights users on 9/3. 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 10/141:05 pm -
1 stop13h 50m
Wed 10/2110:00 am -
2 stops15h 05m
Deal found 9/3![United Airlines logo]()
$665
This Delta deal was found by Cheapflights users on 9/6. 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 11/21:05 pm -
2 stops17h 52m
Mon 11/162:44 pm -
2 stops13h 46m
Deal found 9/6![Delta logo]()
$601
This United Airlines deal was found by Cheapflights users on 9/3. 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 9/266:20 am -
2 stops17h 14m
Sat 10/312:55 pm -
2 stops15h 55m
Deal found 9/3![United Airlines logo]()
$693
This Delta deal was found by Cheapflights users on 9/6. 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 11/16:00 am -
2 stops17h 32m
Mon 11/162:44 pm -
2 stops17h 36m
Deal found 9/6![Delta logo]()
$673
This Delta deal was found by Cheapflights users on 9/4. 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 9/186:00 am -
1 stop15h 15m
Mon 9/215:10 pm -
2 stops16h 35m
Deal found 9/4![Delta logo]()
$708
Last-minute flights from Madrid to ChicagoDiscover last-minute flight deals from Madrid to Chicago. Data last updated September 7, 2026 and is based on user searches.
Discover last-minute flight deals from Madrid to Chicago. Data last updated September 7, 2026 and is based on user searches.
This Rumbo deal was found by Cheapflights users on 9/3. 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.
Wed 9/94:20 pm -
1 stop27h 20m
Sun 9/206:00 pm -
1 stop11h 40m
Deal found 9/3![TAP AIR PORTUGAL logo]()
$629
This United Airlines deal was found by Cheapflights users on 9/4. 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 9/1212:45 pm -
2 stops27h 15m
Sun 9/136:00 pm -
1 stop16h 40m
Deal found 9/4![United Airlines logo]()
$626
This Gotogate deal was found by Cheapflights users on 9/6. 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.
Tue 9/226:05 pm -
1 stop26h 05m
Sun 10/113:00 pm -
1 stop12h 45m
Deal found 9/6![ITA Airways logo]()
$610
This Delta deal was found by Cheapflights users on 9/3. 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 9/236:00 am -
2 stops19h 33m
Wed 12/91:41 pm -
2 stops14h 49m
Deal found 9/3![Delta logo]()
$711
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/17:40 am -
1 stop12h 00m
Sat 10/36:05 pm -
1 stop11h 35m
Deal found 9/3![TAP AIR PORTUGAL logo]()
$563
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/17:40 am -
1 stop12h 00m
Sun 10/116:00 pm -
1 stop33h 05m
Deal found 9/6![TAP AIR PORTUGAL logo]()
$604
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/17:40 am -
1 stop12h 00m
Sat 10/176:05 pm -
1 stop11h 35m
Deal found 9/6![TAP AIR PORTUGAL logo]()
$624
This deal was found by Cheapflights users on 9/7. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1411:15 am -
1 stop14h 26m
Tue 10/2012:55 pm -
1 stop12h 10m
Deal found 9/7![United Airlines logo]()
$591
This Mytrip deal was found by Cheapflights users on 9/6. 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 10/147:20 pm -
2 stops24h 20m
Wed 10/216:00 pm -
2 stops21h 20m
Deal found 9/6![Multiple Airlines logo]()
$615
This deal was found by Cheapflights users on 9/7. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:40 am -
1 stop12h 00m
Thu 10/226:00 pm -
1 stop14h 20m
Deal found 9/7![TAP AIR PORTUGAL logo]()
$589
This Delta deal was found by Cheapflights users on 9/2. 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 10/156:00 am -
2 stops19h 00m
Sun 10/256:44 pm -
2 stops14h 36m
Deal found 9/2![Delta logo]()
$712
This Flighttix deal was found by Cheapflights users on 9/3. 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.
Thu 10/2210:40 am -
1 stop15h 35m
Wed 11/48:05 pm -
1 stop16h 45m
Deal found 9/3![Aer Lingus logo]()
$601
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 September 7, 2026.
Search for one-way flight options from Madrid to Chicago. Find affordable one-way fares based on user searches. Data last updated September 7, 2026.
This KLM deal was found by Cheapflights users on 9/4. 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.
Sun 11/17:00 am -
1 stop14h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![KLM logo]()
$447
This Justfly.com deal was found by Cheapflights users on 9/3. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/210:40 am -
1 stop14h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Iberia logo]()
$448
This Delta deal was found by Cheapflights users on 9/7. 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 10/316:05 am -
1 stop15h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Delta logo]()
$449
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 12/18:20 pm -
2 stops29h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$450
This Kissandfly.com deal was found by Cheapflights users on 9/6. 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.
Fri 9/187:40 am -
1 stop15h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![TAP AIR PORTUGAL logo]()
$451
This Gotogate deal was found by Cheapflights users on 9/4. 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 10/110:25 pm -
1 stop24h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![TAP AIR PORTUGAL logo]()
$452
This Delta deal was found by Cheapflights users on 9/3. 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 12/26:05 am -
2 stops18h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Delta logo]()
$453
This Thrive Travel deal was found by Cheapflights users on 9/7. 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 Thrive Travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:30 am -
1 stop13h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Iberia logo]()
$453
This Delta deal was found by Cheapflights users on 9/7. 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 12/46:05 am -
2 stops19h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Delta logo]()
$454
This Orbitz deal was found by Cheapflights users on 9/4. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:40 am -
1 stop14h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Finnair logo]()
$455
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 11/312:00 pm -
Nonstop9h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Iberia logo]()
$457
This Virgin Atlantic deal was found by Cheapflights users on 9/3. 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.
Mon 11/29:20 am -
2 stops18h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Virgin Atlantic logo]()
$458
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 September 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $560 (American Airlines) |
One-way from | $447 (KLM) |
Popular in | August |
Cheapest in | January |
Average price | $671 |
Good round-trip deal | $696 or less |
Good one-way deal | $528 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 September 7, 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 Madrid Barajas - ORD Chicago O'Hare Intl
MADORD
Madrid Barajas
Wed 10/28
6:05 am-3:25 pm
1 stop15h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$448
MadridChicago
MAD Madrid Barajas - ORD Chicago O'Hare Intl
MADORD
Madrid Barajas
Mon 11/30
6:05 am-2:25 pm
1 stop15h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$448
Quickest round-trip
MadridChicago
MAD Madrid Barajas - ORD Chicago O'Hare Intl
MADORD
Madrid Barajas
Mon 11/30
7:00 am-2:25 pm
1 stop14h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$448
MadridChicago
MAD Madrid Barajas - ORD Chicago O'Hare Intl
MADORD
Madrid Barajas
Sat 10/31
6:05 am-3:25 pm
1 stop15h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$449
MadridChicago
MAD Madrid Barajas - MDW Chicago Midway
MADMDW
Madrid Barajas
Wed 12/2
6:05 am-6:01 pm
2 stops18h 56m
Chicago Midway
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$453
MadridChicago
MAD Madrid Barajas - ORD Chicago O'Hare Intl
MADORD
Madrid Barajas
Wed 12/2
6:05 am-6:26 pm
2 stops19h 21m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$453
MadridChicago
MAD Madrid Barajas - ORD Chicago O'Hare Intl
MADORD
Madrid Barajas
Mon 12/14
6:05 am-7:43 pm
2 stops20h 38m
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 12/4
6:05 am-6:01 pm
2 stops18h 56m
Chicago Midway
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$454
MadridChicago
MAD Madrid Barajas - ORD Chicago O'Hare Intl
MADORD
Madrid Barajas
Fri 12/4
6:05 am-7:43 pm
2 stops20h 38m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$454
MadridChicago
MAD Madrid Barajas - ORD Chicago O'Hare Intl
MADORD
Madrid Barajas
Wed 11/4
6:05 am-4:32 pm
2 stops17h 27m
Chicago O'Hare Intl
Wed 12/31
12:00 am-7:00 am
Nonstop0h 00m
$454
Showing 1-10 of 36 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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 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-MDW
MAD-ORD
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-MDW
MAD-ORD
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 $587). Flying from Madrid to Chicago in August is currently the most expensive (average of $887). 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 September 7, 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 September 7, 2026.
The most flights from MAD to CHI are scheduled on a Monday (10 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (10 on average).
How much does it cost to fly round-trip from Madrid to Chicago?
Airfare is below average for this route at the moment.
Madrid to Chicago flights typically cost between $616 and $738 in November.The cheapest round-trip price found within the last 5 days was $560 on American Airlines (Nov 6-Nov 16).
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 172 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 11% 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 62 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 September 7, 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.
Overall
7.6
Boarding
7.7
Crew
8.2
Food
6.7
Comfort
7.4
Entertainment
6.9
Reviews
1 / 20
10.0
ExcellentJake,Jun 2026
RNO - SEA
Overall
7.6
Boarding
7.7
Crew
8.2
Food
6.7
Comfort
7.4
Entertainment
6.9
Reviews
1 / 20
10.0
ExcellentJake,Jun 2026
RNO - SEA
Overall
7.6
Boarding
7.7
Crew
8.2
Food
6.7
Comfort
7.4
Entertainment
6.9
Reviews
1 / 20
10.0
ExcellentJake,Jun 2026
RNO - SEA
Overall
7.6
Boarding
7.7
Crew
8.2
Food
6.7
Comfort
7.4
Entertainment
6.9
Reviews
1 / 20
10.0
ExcellentJake,Jun 2026
RNO - SEA
Overall
7.6
Boarding
7.7
Crew
8.2
Food
6.7
Comfort
7.4
Entertainment
6.9
Reviews
1 / 20
10.0
ExcellentJake,Jun 2026
RNO - SEA
Overall
7.6
Boarding
7.7
Crew
8.2
Food
6.7
Comfort
7.4
Entertainment
6.9
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
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Madrid
Popular flights
Alternative routes for Madrid to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
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 September 7, 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 September 7, 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 September 7, 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 September 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$448 | Average$614 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$493 | Average$915 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$514 | Average$690 | FlexibilityNo cancel fee | On-time76% |