$328+ Cheap flights from Chicago (CHI) to Madrid, Spain (MAD)
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 11/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MAD
Oct 7 — Oct 141
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Madrid 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 Chicago to Madrid Barajas are usually found in February or January, booked 51 days in advance, depart on a Wednesday or Tuesday and return on a Thursday
Cheap flight deals from Chicago to Madrid
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Cheapest flights from Chicago to MadridExplore the most affordable flight options available from Chicago to Madrid. 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 Chicago to Madrid. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 7, 2026.
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.
Sun 12/69:34 pm -
2 stops27h 26m
Thu 12/106:05 am -
1 stop14h 05m
Deal found 9/5![Multiple Airlines logo]()
$693
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:05 pm -
Nonstop8h 20m
Tue 11/106:00 pm -
1 stop28h 30m
Deal found 9/7![Multiple Airlines logo]()
$696
This Finnair 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/204:55 pm -
Nonstop8h 25m
Thu 10/2912:40 pm -
Nonstop9h 20m
Deal found 9/3![Finnair logo]()
$697
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/43:55 pm -
1 stop11h 00m
Wed 11/1110:40 am -
1 stop14h 40m
Deal found 9/4![Aer Lingus logo]()
$698
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 10/59:46 am -
1 stop19h 29m
Wed 10/146:00 am -
1 stop15h 30m
Deal found 9/3![Delta logo]()
$699
This lol.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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:40 pm -
Nonstop8h 10m
Wed 11/1112:00 pm -
Nonstop9h 55m
Deal found 9/7![Finnair logo]()
$700
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 12/124:45 pm -
1 stop33h 30m
Tue 12/221:25 pm -
1 stop28h 42m
Deal found 9/7![United Airlines logo]()
$702
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.
Sun 9/205:10 pm -
1 stop16h 35m
Mon 10/121:05 pm -
1 stop32h 10m
Deal found 9/3![Delta logo]()
$703
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:00 pm -
1 stop20h 25m
Thu 9/174:20 pm -
1 stop30h 40m
Deal found 9/3![TAP AIR PORTUGAL logo]()
$704
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.
Wed 11/118:50 am -
2 stops16h 10m
Wed 11/181:25 pm -
2 stops29h 21m
Deal found 9/6![United Airlines logo]()
$705
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/35:40 pm -
Nonstop8h 10m
Tue 11/109:10 pm -
1 stop25h 20m
Deal found 9/4![Multiple Airlines logo]()
$706
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/111:05 pm -
1 stop13h 40m
Wed 11/1812:20 pm -
1 stop17h 34m
Deal found 9/3![KLM logo]()
$712
Best flights from Chicago to MadridDiscover carefully curated flight deals from Chicago to Madrid 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 Chicago to Madrid that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 7, 2026.
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/45:10 pm -
1 stop12h 05m
Fri 11/1312:40 pm -
Nonstop9h 25m
Deal found 9/5![Multiple Airlines logo]()
$708
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.
Mon 10/195:29 pm -
2 stops15h 06m
Thu 10/226:00 am -
1 stop15h 15m
Deal found 9/4![Delta logo]()
$708
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/911:27 am -
1 stop15h 18m
Fri 11/1312:20 pm -
1 stop17h 34m
Deal found 9/6![KLM logo]()
$722
This Scandinavian 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:15 pm -
2 stops32h 15m
Sun 11/1511:20 am -
2 stops36h 25m
Deal found 9/6![Scandinavian Airlines logo]()
$738
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.
Tue 12/86:04 pm -
1 stop30h 41m
Sat 12/121:25 pm -
1 stop28h 42m
Deal found 9/7![United Airlines logo]()
$752
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 12/311:28 am -
1 stop15h 17m
Sat 12/1212:20 pm -
1 stop17h 35m
Deal found 9/2![Virgin Atlantic logo]()
$810
This Finnair 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/109:50 pm -
1 stop12h 15m
Wed 2/1712:00 pm -
Nonstop9h 55m
Deal found 9/5![Multiple Airlines logo]()
$710
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.
Sat 9/195:10 pm -
1 stop19h 05m
Wed 10/146:00 am -
1 stop15h 30m
Deal found 9/3![Delta logo]()
$753
This Scandinavian 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:15 pm -
2 stops32h 50m
Sun 11/811:20 am -
2 stops36h 25m
Deal found 9/4![Scandinavian Airlines logo]()
$754
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/149:41 pm -
2 stops28h 34m
Sun 11/221:25 pm -
3 stops39h 53m
Deal found 9/2![United Airlines logo]()
$767
This United 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/281:55 pm -
1 stop11h 05m
Mon 11/97:30 pm -
1 stop27h 45m
Deal found 9/2![Multiple Airlines logo]()
$712
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2912:49 pm -
1 stop14h 56m
Sat 11/712:20 pm -
1 stop17h 13m
Deal found 9/3![KLM logo]()
$812
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.
Sat 11/149:30 am -
2 stops17h 15m
Sun 11/229:20 am -
2 stops20h 34m
Deal found 9/2![Virgin Atlantic logo]()
$815
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.
Tue 12/89:37 am -
2 stops17h 08m
Sat 12/129:20 am -
2 stops20h 35m
Deal found 9/3![Delta logo]()
$766
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/1410:00 am -
2 stops16h 15m
Sat 3/2712:25 pm -
1 stop32h 23m
Deal found 9/5![United Airlines logo]()
$774
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.
Tue 2/91:00 pm -
2 stops15h 30m
Sat 2/2012:20 pm -
1 stop16h 50m
Deal found 9/4![Delta logo]()
$771
This Virgin Atlantic 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 Virgin Atlantic is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/126:00 am -
2 stops18h 20m
Fri 4/912:45 pm -
2 stops16h 25m
Deal found 9/7![Virgin Atlantic logo]()
$856
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:00 am -
2 stops20h 05m
Wed 10/286:25 am -
1 stop12h 45m
Deal found 9/5![United Airlines logo]()
$780
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:10 pm -
1 stop12h 10m
Sun 11/1512:40 pm -
Nonstop9h 25m
Deal found 9/4![Multiple Airlines logo]()
$795
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.
Mon 12/289:30 am -
2 stops17h 25m
Sat 1/910:00 am -
2 stops19h 10m
Deal found 9/5![Delta logo]()
$790
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.
Fri 10/306:44 pm -
2 stops15h 21m
Sun 11/86:05 am -
2 stops18h 55m
Deal found 9/6![Delta logo]()
$832
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.
Thu 11/56:04 am -
2 stops18h 16m
Fri 11/1312:20 pm -
1 stop17h 34m
Deal found 9/5![Delta logo]()
$876
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.
Tue 10/205:09 pm -
1 stop12h 06m
Wed 11/412:20 pm -
1 stop17h 13m
Deal found 9/5![Delta logo]()
$886
Last-minute flights from Chicago to MadridDiscover last-minute flight deals from Chicago to Madrid. Data last updated September 7, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Madrid. Data last updated September 7, 2026 and is based on user searches.
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:00 pm -
1 stop16h 00m
Thu 9/174:20 pm -
1 stop30h 40m
Deal found 9/4![TAP AIR PORTUGAL logo]()
$696
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.
Sun 9/205:10 pm -
1 stop16h 35m
Mon 10/121:05 pm -
1 stop32h 10m
Deal found 9/3![Delta logo]()
$703
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.
Sun 9/201:55 pm -
2 stops18h 40m
Tue 10/201:05 pm -
1 stop32h 25m
Deal found 9/3![Delta logo]()
$708
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.
Tue 9/221:00 pm -
2 stops15h 20m
Tue 9/299:50 am -
1 stop19h 54m
Deal found 9/4![Delta logo]()
$716
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:50 pm -
1 stop16h 05m
Wed 10/73:20 pm -
1 stop14h 10m
Deal found 9/3![Iberia logo]()
$705
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2710:15 pm -
Nonstop8h 15m
Wed 10/73:20 pm -
1 stop14h 10m
Deal found 9/3![American Airlines logo]()
$707
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 10/59:46 am -
1 stop19h 29m
Wed 10/146:00 am -
1 stop15h 30m
Deal found 9/3![Delta logo]()
$699
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.
Tue 10/1312:49 pm -
1 stop16h 26m
Tue 10/206:00 am -
2 stops19h 00m
Deal found 9/3![Delta logo]()
$713
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/153:45 pm -
1 stop11h 10m
Thu 10/2211:45 am -
Nonstop9h 40m
Deal found 9/3![Multiple Airlines logo]()
$700
This Finnair 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/204:55 pm -
Nonstop8h 25m
Thu 10/2912:40 pm -
Nonstop9h 20m
Deal found 9/3![Finnair logo]()
$697
This Justfly.com 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:00 pm -
1 stop23h 20m
Sat 10/316:00 pm -
1 stop28h 30m
Deal found 9/7![TAP AIR PORTUGAL logo]()
$706
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:00 am -
1 stop22h 15m
Thu 11/121:25 pm -
1 stop32h 27m
Deal found 9/5![United Airlines logo]()
$702
One-way flights from Chicago to MadridSearch for one-way flight options from Chicago to Madrid. Find affordable one-way fares based on user searches. Data last updated September 7, 2026.
Search for one-way flight options from Chicago to Madrid. Find affordable one-way fares based on user searches. Data last updated September 7, 2026.
This British Airways 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/299:50 pm -
1 stop28h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![British Airways logo]()
$328
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1010:35 am -
1 stop18h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![KLM logo]()
$329
This Air France 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2710:30 am -
1 stop12h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Air France logo]()
$329
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 10/56:05 am -
1 stop23h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Delta logo]()
$330
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2710:25 pm -
2 stops35h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Multiple Airlines logo]()
$330
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.
Mon 11/911:27 am -
1 stop15h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![KLM logo]()
$331
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.
Mon 11/911:05 am -
2 stops15h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![United Airlines logo]()
$331
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.
Fri 10/23:20 pm -
2 stops35h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$332
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:10 pm -
1 stop11h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Air France logo]()
$332
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/83:20 pm -
3 stops35h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Multiple Airlines logo]()
$333
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/12:00 pm -
2 stops35h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Air Canada logo]()
$333
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.
Wed 2/109:55 am -
2 stops14h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Delta logo]()
$334
Find flight deals from Chicago to Madrid
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Madrid (MAD). 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 | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $693 (Expedia) |
One-way from | $328 (British Airways) |
Popular in | June |
Cheapest in | February |
Average price | $834 |
Good round-trip deal | $848 or less |
Good one-way deal | $440 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Madrid 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 Chicago to Madrid that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMadrid
MDW Chicago Midway - MAD Madrid Barajas
MDWMAD
Chicago Midway
Wed 2/10
9:55 am-7:20 am
2 stops14h 25m
Madrid Barajas
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$329
ChicagoMadrid
MDW Chicago Midway - MAD Madrid Barajas
MDWMAD
Chicago Midway
Mon 10/26
1:27 pm-9:45 am
2 stops14h 18m
Madrid Barajas
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$334
ChicagoMadrid
ORD Chicago O'Hare Intl - MAD Madrid Barajas
ORDMAD
Chicago O'Hare Intl
Sun 11/8
7:00 am-9:15 am
2 stops19h 15m
Madrid Barajas
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$334
ChicagoMadrid
MDW Chicago Midway - MAD Madrid Barajas
MDWMAD
Chicago Midway
Mon 10/26
12:49 pm-9:45 am
1 stop14h 56m
Madrid Barajas
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$334
ChicagoMadrid
ORD Chicago O'Hare Intl - MAD Madrid Barajas
ORDMAD
Chicago O'Hare Intl
Mon 11/9
6:00 pm-5:45 pm
2 stops16h 45m
Madrid Barajas
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$334
ChicagoMadrid
ORD Chicago O'Hare Intl - MAD Madrid Barajas
ORDMAD
Chicago O'Hare Intl
Sat 12/5
9:34 pm-9:15 am
1 stop28h 41m
Madrid Barajas
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$335
ChicagoMadrid
ORD Chicago O'Hare Intl - MAD Madrid Barajas
ORDMAD
Chicago O'Hare Intl
Wed 11/4
7:00 am-8:00 am
2 stops18h 00m
Madrid Barajas
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$338
ChicagoMadrid
ORD Chicago O'Hare Intl - MAD Madrid Barajas
ORDMAD
Chicago O'Hare Intl
Wed 9/30
10:29 am-9:30 am
2 stops16h 01m
Madrid Barajas
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$338
ChicagoMadrid
MDW Chicago Midway - MAD Madrid Barajas
MDWMAD
Chicago Midway
Thu 10/8
3:20 pm-1:25 pm
2 stops39h 05m
Madrid Barajas
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$340
ChicagoMadrid
ORD Chicago O'Hare Intl - MAD Madrid Barajas
ORDMAD
Chicago O'Hare Intl
Thu 10/1
9:15 pm-9:40 am
1 stop29h 25m
Madrid Barajas
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$373
Showing 1-10 of 37 resultsSorted by cheapest first
Compare providers for flights from Chicago to Madrid
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 Chicago to Madrid 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 | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Madrid flights, users find the pricing of Ovago to be most consistent on Cheapflights vs. Ovago Users can find the same prices on Chicago-Madrid flight deals on Cheapflights vs. Ovago >95% of the time. Price accuracy is based on data collected from Chicago-Madrid flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Madrid flights, Cheapflights users trust Ovago the most. Ovago 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 Chicago-Madrid 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 Chicago to Madrid
Have a flexible travel schedule? Discover the best time to fly to Madrid from Chicago with our price prediction graph.
CHI-MAD
ORD-MAD
MDW-MAD
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 Chicago to Madrid
CHI-MAD
ORD-MAD
MDW-MAD
What is the cheapest month to book a flight from Chicago to Madrid?
Currently, February is the cheapest month in which you can book a flight from Chicago to Madrid (average of $548). Flying from Chicago to Madrid in December is currently the most expensive (average of $1,098). 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 CHI to MAD?
Find hourly flight availability from Chicago to Madrid. 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.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Madrid as you normally would.
Weekly flight availability from Chicago to Madrid
Explore weekly flight availability from Chicago to Madrid. 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 CHI to MAD 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 (6 on average).
How much does it cost to fly round-trip from Chicago to Madrid?
Airfare is typical for this route at the moment.
Chicago to Madrid flights typically cost between $688 and $978 in December.The cheapest round-trip price found within the last 5 days was $693 on Multiple Airlines (Dec 6-Dec 10).
What’s the top layover airport for flights from Chicago to Madrid?
Share of 1-stop round-trip flights from Chicago to Madrid chosen by Cheapflights users in the past 12 months, using the same layover each way.
Lisbon (LIS) – chosen by Cheapflights users on 80% of 1-stop itineraries from Chicago to Madrid on Cheapflights.
What’s the cheapest layover airport for flights from Chicago to Madrid?
Average round-trip fare for 1-stop flights from Chicago to Madrid, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Copenhagen (CPH) is the most affordable 1-stop option, with an average round-trip price of $515.
What’s the fastest layover option from Chicago to Madrid?
Shortest average travel time for 1-stop one-way flights from Chicago to Madrid, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Lisbon (LIS) have the shortest average one-way travel time for 1-stop routes: 11h 25m.
Which airport typically offers the quickest layover for flights from Chicago to Madrid?
Average layover duration for 1-stop one-way flights from Chicago to Madrid, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Lisbon (LIS) offer the fastest connection on this route, with an average layover time of 6h 13m.
How often are flights from Chicago to Madrid delayed?
About 37% of weekly flights between Chicago and Madrid have experienced delays in the past year, with the average delay time being 148 minutes.
What is the most punctual flight time for Chicago to Madrid flights?
Historically, flights departing at night 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 Tuesday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Madrid flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 31% of flights being delayed.
How far ahead should I book a flight from Chicago to Madrid?
The price you pay for your flight from Chicago to Madrid may vary depending on when you book. For the best chance of a lower fare, look to book 7 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
The best insider tips for Chicago to Madrid 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 Chicago to Madrid trip
Our travel experts
Reviews of airlines servicing Madrid
Get insights into the airlines that provide service to Madrid. 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 Madrid. Reviews last updated September 7, 2026.
Peruse reviews from past customers who have flown with Finnair,TAP AIR PORTUGAL, andAmerican Airlines from Chicago to Madrid to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.6
Comfort
7.4
Food
6.7
Crew
8.2
Entertainment
6.9
Boarding
7.7
Reviews
1 / 20
10.0
ExcellentJake,Jun 2026
RNO - SEA
Overall
7.6
Comfort
7.4
Food
6.7
Crew
8.2
Entertainment
6.9
Boarding
7.7
Reviews
1 / 20
10.0
ExcellentJake,Jun 2026
RNO - SEA
Overall
7.6
Comfort
7.4
Food
6.7
Crew
8.2
Entertainment
6.9
Boarding
7.7
Reviews
1 / 20
10.0
ExcellentJake,Jun 2026
RNO - SEA
Overall
7.6
Comfort
7.4
Food
6.7
Crew
8.2
Entertainment
6.9
Boarding
7.7
Reviews
1 / 20
10.0
ExcellentJake,Jun 2026
RNO - SEA
Overall
7.6
Comfort
7.4
Food
6.7
Crew
8.2
Entertainment
6.9
Boarding
7.7
Reviews
1 / 20
10.0
ExcellentJake,Jun 2026
RNO - SEA
Overall
7.6
Comfort
7.4
Food
6.7
Crew
8.2
Entertainment
6.9
Boarding
7.7
Reviews
1 / 20
10.0
ExcellentJake,Jun 2026
RNO - SEA
Related info for your journey
Find useful and relevant information for your journey from Chicago to Madrid. 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 Madrid?
Book flights to Madrid if you plan to visit one of these locationsGetafe
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Explore flights to Madrid departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 7, 2026.
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Top 10 airlines flying from Chicago to Madrid
Discover the top 10 airlines that operate flights from Chicago to Madrid. 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$215 | Average$426 | FlexibilityNo cancel fee | On-time72% | |
| Cheapest$348 | Average$627 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$471 | Average$708 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$472 | Average$686 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$472 | Average$764 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$474 | Average$735 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$475 | Average$835 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$476 | Average$630 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$479 | Average$745 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$486 | Average$537 | FlexibilityNo cancel fee | On-time77% |