One Way Flights from Chicago to Madrid (MDW to MAD)

Discover more affordable routes and cheaper dates from Chicago to Madrid (MDW to MAD) within a date range.

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  • US$721
    Frontier AirlinesAir Europa
    7:35am - 1:00pm
    Tue Dec 24th 2024
    22h 25m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Tue Dec 24th 2024 Frontier Airlines · F9 2110 Depart at 7:35am from Chicago (MDW) Fly for 3h 13m Arrive at 11:48am in Miami (MIA)

    Layover in Miami for 10h 52m

    Tue Dec 24th 2024 Air Europa · UX 98 Depart at 10:40pm from Miami (MIA) Fly for 8h 20m Arrive at 1:00pm in Madrid (MAD)

    Book Flight Find Accommodations
  • US$860
    Frontier AirlinesAir Europa
    6:00am - 1:50pm
    Sun Dec 22nd 2024
    24h 50m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Sun Dec 22nd 2024 Frontier Airlines · F9 2110 Depart at 6:00am from Chicago (MDW) Fly for 3h 13m Arrive at 10:13am in Miami (MIA)

    Layover in Miami for 13h 17m

    Sun Dec 22nd 2024 Air Europa · UX 90 Depart at 11:30pm from Miami (MIA) Fly for 8h 20m Arrive at 1:50pm in Madrid (MAD)

    Book Flight Find Accommodations
  • US$970
    Frontier AirlinesAir Europa
    6:00am - 12:05pm
    Sun Dec 22nd 2024
    23h 5m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Sun Dec 22nd 2024 Frontier Airlines · F9 2110 Depart at 6:00am from Chicago (MDW) Fly for 3h 13m Arrive at 10:13am in Miami (MIA)

    Layover in Miami for 11h 32m

    Sun Dec 22nd 2024 Air Europa · UX 98 Depart at 9:45pm from Miami (MIA) Fly for 8h 20m Arrive at 12:05pm in Madrid (MAD)

    Book Flight Find Accommodations
  • US$1017
    Frontier AirlinesAir Europa
    9:16am - 12:05pm
    Mon Dec 23rd 2024
    19h 49m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Mon Dec 23rd 2024 Frontier Airlines · F9 2110 Depart at 9:16am from Chicago (MDW) Fly for 3h 14m Arrive at 1:30pm in Miami (MIA)

    Layover in Miami for 8h 15m

    Mon Dec 23rd 2024 Air Europa · UX 98 Depart at 9:45pm from Miami (MIA) Fly for 8h 20m Arrive at 12:05pm in Madrid (MAD)

    Book Flight Find Accommodations
  • US$1187
    Frontier AirlinesIberia Airlines
    9:16am - 7:55am
    Mon Dec 23rd 2024
    15h 39m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Mon Dec 23rd 2024 Frontier Airlines · F9 2110 Depart at 9:16am from Chicago (MDW) Fly for 3h 14m Arrive at 1:30pm in Miami (MIA)

    Layover in Miami for 3h 50m

    Mon Dec 23rd 2024 Iberia Airlines · IB 334 Depart at 5:20pm from Miami (MIA) Fly for 8h 35m Arrive at 7:55am in Madrid (MAD)

    Book Flight Find Accommodations
  • US$1187
    Frontier AirlinesIberia Airlines
    9:16am - 12:50pm
    Mon Dec 23rd 2024
    20h 34m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Mon Dec 23rd 2024 Frontier Airlines · F9 2110 Depart at 9:16am from Chicago (MDW) Fly for 3h 14m Arrive at 1:30pm in Miami (MIA)

    Layover in Miami for 8h 45m

    Mon Dec 23rd 2024 Iberia Airlines · IB 338 Depart at 10:15pm from Miami (MIA) Fly for 8h 35m Arrive at 12:50pm in Madrid (MAD)

    Book Flight Find Accommodations
  • US$1266
    VolarisAeroMéxico
    7:55pm - 4:55am
    Sun Dec 22nd 2024
    26h 0m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Sun Dec 22nd 2024 Volaris · Y4 1841 Depart at 7:55pm from Chicago (MDW) Fly for 4h 29m Arrive at 12:24am in Guadalajara (GDL)

    Layover in Guadalajara for 10h 41m

    Mon Dec 23rd 2024 AeroMéxico · AM 36 Depart at 11:05am from Guadalajara (GDL) Fly for 10h 50m Arrive at 4:55am in Madrid (MAD)

    Book Flight Find Accommodations
  • US$1326
    Frontier AirlinesIberia Airlines
    6:00am - 7:55am
    Sun Dec 22nd 2024
    18h 55m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Sun Dec 22nd 2024 Frontier Airlines · F9 2110 Depart at 6:00am from Chicago (MDW) Fly for 3h 13m Arrive at 10:13am in Miami (MIA)

    Layover in Miami for 7h 7m

    Sun Dec 22nd 2024 Iberia Airlines · IB 334 Depart at 5:20pm from Miami (MIA) Fly for 8h 35m Arrive at 7:55am in Madrid (MAD)

    Book Flight Find Accommodations
  • US$1326
    Frontier AirlinesIberia Airlines
    6:00am - 12:50pm
    Sun Dec 22nd 2024
    23h 50m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Sun Dec 22nd 2024 Frontier Airlines · F9 2110 Depart at 6:00am from Chicago (MDW) Fly for 3h 13m Arrive at 10:13am in Miami (MIA)

    Layover in Miami for 12h 2m

    Sun Dec 22nd 2024 Iberia Airlines · IB 338 Depart at 10:15pm from Miami (MIA) Fly for 8h 35m Arrive at 12:50pm in Madrid (MAD)

    Book Flight Find Accommodations
  • US$1328
    Virgin Atlantic AirwaysVirgin Atlantic Airways
    10:08am - 9:00am
    Tue Dec 24th 2024
    15h 52m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Tue Dec 24th 2024 Virgin Atlantic Airways · VS 2618 Depart at 10:08am from Chicago (MDW) Fly for 1h 55m Arrive at 1:03pm in Atlanta (ATL)

    Layover in Atlanta for 5h 42m

    Tue Dec 24th 2024 Virgin Atlantic Airways · VS 3884 Depart at 6:45pm from Atlanta (ATL) Fly for 8h 15m Arrive at 9:00am in Madrid (MAD)

    Book Flight Find Accommodations
  • US$1330
    Virgin Atlantic AirwaysVirgin Atlantic Airways
    6:00am - 9:00am
    Tue Dec 24th 2024
    20h 0m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Tue Dec 24th 2024 Virgin Atlantic Airways · VS 2620 Depart at 6:00am from Chicago (MDW) Fly for 1h 58m Arrive at 8:58am in Atlanta (ATL)

    Layover in Atlanta for 9h 47m

    Tue Dec 24th 2024 Virgin Atlantic Airways · VS 3884 Depart at 6:45pm from Atlanta (ATL) Fly for 8h 15m Arrive at 9:00am in Madrid (MAD)

    Book Flight Find Accommodations
  • US$1348
    Frontier AirlinesIberia Airlines
    7:35am - 12:50pm
    Tue Dec 24th 2024
    22h 15m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Tue Dec 24th 2024 Frontier Airlines · F9 2110 Depart at 7:35am from Chicago (MDW) Fly for 3h 13m Arrive at 11:48am in Miami (MIA)

    Layover in Miami for 10h 27m

    Tue Dec 24th 2024 Iberia Airlines · IB 338 Depart at 10:15pm from Miami (MIA) Fly for 8h 35m Arrive at 12:50pm in Madrid (MAD)

    Book Flight Find Accommodations
  • US$1396
    Frontier AirlinesIberia Airlines
    6:00am - 7:55am
    Thu Dec 19th 2024
    18h 55m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Thu Dec 19th 2024 Frontier Airlines · F9 2110 Depart at 6:00am from Chicago (MDW) Fly for 3h 13m Arrive at 10:13am in Miami (MIA)

    Layover in Miami for 7h 7m

    Thu Dec 19th 2024 Iberia Airlines · IB 334 Depart at 5:20pm from Miami (MIA) Fly for 8h 35m Arrive at 7:55am in Madrid (MAD)

    Book Flight Find Accommodations
  • US$1396
    Frontier AirlinesIberia Airlines
    6:00am - 12:50pm
    Thu Dec 19th 2024
    23h 50m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Thu Dec 19th 2024 Frontier Airlines · F9 2110 Depart at 6:00am from Chicago (MDW) Fly for 3h 13m Arrive at 10:13am in Miami (MIA)

    Layover in Miami for 12h 2m

    Thu Dec 19th 2024 Iberia Airlines · IB 338 Depart at 10:15pm from Miami (MIA) Fly for 8h 35m Arrive at 12:50pm in Madrid (MAD)

    Book Flight Find Accommodations
  • US$1405
    Frontier AirlinesIberia Airlines
    8:00am - 2:25pm
    Thu Dec 19th 2024
    23h 25m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Thu Dec 19th 2024 Frontier Airlines · F9 1887 Depart at 8:00am from Chicago (MDW) Fly for 2h 50m Arrive at 10:50am in Dallas (DFW)

    Layover in Dallas for 11h 15m

    Thu Dec 19th 2024 Iberia Airlines · IB 364 Depart at 10:05pm from Dallas (DFW) Fly for 9h 20m Arrive at 2:25pm in Madrid (MAD)

    Book Flight Find Accommodations
  • US$1407
    Frontier AirlinesAir Europa
    7:35am - 1:00pm
    Sat Dec 21st 2024
    22h 25m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Sat Dec 21st 2024 Frontier Airlines · F9 2110 Depart at 7:35am from Chicago (MDW) Fly for 3h 13m Arrive at 11:48am in Miami (MIA)

    Layover in Miami for 10h 52m

    Sat Dec 21st 2024 Air Europa · UX 98 Depart at 10:40pm from Miami (MIA) Fly for 8h 20m Arrive at 1:00pm in Madrid (MAD)

    Book Flight Find Accommodations
  • US$1422
    Frontier AirlinesIberia Airlines
    8:00am - 2:25pm
    Sun Dec 22nd 2024
    23h 25m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Sun Dec 22nd 2024 Frontier Airlines · F9 1887 Depart at 8:00am from Chicago (MDW) Fly for 2h 50m Arrive at 10:50am in Dallas (DFW)

    Layover in Dallas for 11h 15m

    Sun Dec 22nd 2024 Iberia Airlines · IB 364 Depart at 10:05pm from Dallas (DFW) Fly for 9h 20m Arrive at 2:25pm in Madrid (MAD)

    Book Flight Find Accommodations
  • US$1459
    Frontier AirlinesIberia Airlines
    7:35am - 7:55am
    Sat Dec 21st 2024
    17h 20m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Sat Dec 21st 2024 Frontier Airlines · F9 2110 Depart at 7:35am from Chicago (MDW) Fly for 3h 13m Arrive at 11:48am in Miami (MIA)

    Layover in Miami for 5h 32m

    Sat Dec 21st 2024 Iberia Airlines · IB 334 Depart at 5:20pm from Miami (MIA) Fly for 8h 35m Arrive at 7:55am in Madrid (MAD)

    Book Flight Find Accommodations
  • US$1459
    Frontier AirlinesIberia Airlines
    7:35am - 12:50pm
    Sat Dec 21st 2024
    22h 15m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Sat Dec 21st 2024 Frontier Airlines · F9 2110 Depart at 7:35am from Chicago (MDW) Fly for 3h 13m Arrive at 11:48am in Miami (MIA)

    Layover in Miami for 10h 27m

    Sat Dec 21st 2024 Iberia Airlines · IB 338 Depart at 10:15pm from Miami (MIA) Fly for 8h 35m Arrive at 12:50pm in Madrid (MAD)

    Book Flight Find Accommodations
  • US$1477
    VolarisAeroMéxico
    7:55pm - 4:55am
    Mon Dec 23rd 2024
    26h 0m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Mon Dec 23rd 2024 Volaris · Y4 1843 Depart at 7:55pm from Chicago (MDW) Fly for 4h 29m Arrive at 12:24am in Guadalajara (GDL)

    Layover in Guadalajara for 10h 41m

    Tue Dec 24th 2024 AeroMéxico · AM 36 Depart at 11:05am from Guadalajara (GDL) Fly for 10h 50m Arrive at 4:55am in Madrid (MAD)

    Book Flight Find Accommodations
  • US$1564
    Frontier AirlinesAir Europa
    9:16am - 12:05pm
    Fri Dec 20th 2024
    19h 49m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Fri Dec 20th 2024 Frontier Airlines · F9 2110 Depart at 9:16am from Chicago (MDW) Fly for 3h 14m Arrive at 1:30pm in Miami (MIA)

    Layover in Miami for 8h 15m

    Fri Dec 20th 2024 Air Europa · UX 98 Depart at 9:45pm from Miami (MIA) Fly for 8h 20m Arrive at 12:05pm in Madrid (MAD)

    Book Flight Find Accommodations
  • US$1589
    Frontier AirlinesIberia Airlines
    7:35am - 7:55am
    Tue Dec 24th 2024
    17h 20m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Tue Dec 24th 2024 Frontier Airlines · F9 2110 Depart at 7:35am from Chicago (MDW) Fly for 3h 13m Arrive at 11:48am in Miami (MIA)

    Layover in Miami for 5h 32m

    Tue Dec 24th 2024 Iberia Airlines · IB 334 Depart at 5:20pm from Miami (MIA) Fly for 8h 35m Arrive at 7:55am in Madrid (MAD)

    Book Flight Find Accommodations
  • US$1882
    Virgin Atlantic AirwaysVirgin Atlantic Airways
    5:03pm - 9:00am
    Sat Dec 21st 2024
    32h 57m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Sat Dec 21st 2024 Virgin Atlantic Airways · VS 2620 Depart at 5:03pm from Chicago (MDW) Fly for 2h 3m Arrive at 8:06pm in Atlanta (ATL)

    Layover in Atlanta for 22h 39m

    Sun Dec 22nd 2024 Virgin Atlantic Airways · VS 3884 Depart at 6:45pm from Atlanta (ATL) Fly for 8h 15m Arrive at 9:00am in Madrid (MAD)

    Book Flight Find Accommodations
  • US$2293
    Virgin Atlantic AirwaysVirgin Atlantic Airways
    12:10pm - 9:00am
    Sat Dec 21st 2024
    13h 50m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Sat Dec 21st 2024 Virgin Atlantic Airways · VS 2619 Depart at 12:10pm from Chicago (MDW) Fly for 1h 53m Arrive at 3:03pm in Atlanta (ATL)

    Layover in Atlanta for 3h 42m

    Sat Dec 21st 2024 Virgin Atlantic Airways · VS 3884 Depart at 6:45pm from Atlanta (ATL) Fly for 8h 15m Arrive at 9:00am in Madrid (MAD)

    Book Flight Find Accommodations
  • US$2293
    Virgin Atlantic AirwaysVirgin Atlantic Airways
    10:08am - 9:00am
    Sat Dec 21st 2024
    15h 52m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Sat Dec 21st 2024 Virgin Atlantic Airways · VS 2618 Depart at 10:08am from Chicago (MDW) Fly for 1h 55m Arrive at 1:03pm in Atlanta (ATL)

    Layover in Atlanta for 5h 42m

    Sat Dec 21st 2024 Virgin Atlantic Airways · VS 3884 Depart at 6:45pm from Atlanta (ATL) Fly for 8h 15m Arrive at 9:00am in Madrid (MAD)

    Book Flight Find Accommodations
  • US$2296
    Virgin Atlantic AirwaysVirgin Atlantic Airways
    12:20pm - 9:00am
    Fri Dec 20th 2024
    13h 40m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Fri Dec 20th 2024 Virgin Atlantic Airways · VS 2619 Depart at 12:20pm from Chicago (MDW) Fly for 1h 56m Arrive at 3:16pm in Atlanta (ATL)

    Layover in Atlanta for 3h 29m

    Fri Dec 20th 2024 Virgin Atlantic Airways · VS 3884 Depart at 6:45pm from Atlanta (ATL) Fly for 8h 15m Arrive at 9:00am in Madrid (MAD)

    Book Flight Find Accommodations
  • US$2296
    Virgin Atlantic AirwaysVirgin Atlantic Airways
    10:08am - 9:00am
    Fri Dec 20th 2024
    15h 52m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Fri Dec 20th 2024 Virgin Atlantic Airways · VS 2618 Depart at 10:08am from Chicago (MDW) Fly for 1h 55m Arrive at 1:03pm in Atlanta (ATL)

    Layover in Atlanta for 5h 42m

    Fri Dec 20th 2024 Virgin Atlantic Airways · VS 3884 Depart at 6:45pm from Atlanta (ATL) Fly for 8h 15m Arrive at 9:00am in Madrid (MAD)

    Book Flight Find Accommodations
  • US$2433
    Frontier AirlinesVirgin Atlantic Airways
    8:25am - 9:00am
    Fri Dec 20th 2024
    17h 35m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Fri Dec 20th 2024 Frontier Airlines · F9 2780 Depart at 8:25am from Chicago (MDW) Fly for 2h 4m Arrive at 11:29am in Atlanta (ATL)

    Layover in Atlanta for 7h 16m

    Fri Dec 20th 2024 Virgin Atlantic Airways · VS 3884 Depart at 6:45pm from Atlanta (ATL) Fly for 8h 15m Arrive at 9:00am in Madrid (MAD)

    Book Flight Find Accommodations
  • US$2465
    VolarisAeroMéxico
    7:55pm - 4:55am
    Sat Dec 21st 2024
    26h 0m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Sat Dec 21st 2024 Volaris · Y4 1841 Depart at 7:55pm from Chicago (MDW) Fly for 4h 29m Arrive at 12:24am in Guadalajara (GDL)

    Layover in Guadalajara for 10h 41m

    Sun Dec 22nd 2024 AeroMéxico · AM 36 Depart at 11:05am from Guadalajara (GDL) Fly for 10h 50m Arrive at 4:55am in Madrid (MAD)

    Book Flight Find Accommodations
  • US$3185
    VolarisAeroMéxico
    7:55pm - 4:55am
    Thu Dec 19th 2024
    26h 0m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Thu Dec 19th 2024 Volaris · Y4 1841 Depart at 7:55pm from Chicago (MDW) Fly for 4h 29m Arrive at 12:24am in Guadalajara (GDL)

    Layover in Guadalajara for 10h 41m

    Fri Dec 20th 2024 AeroMéxico · AM 36 Depart at 11:05am from Guadalajara (GDL) Fly for 10h 50m Arrive at 4:55am in Madrid (MAD)

    Book Flight Find Accommodations
  • US$3622
    Frontier AirlinesIberia Airlines
    2:15pm - 2:25pm
    Fri Dec 20th 2024
    17h 10m
    Chicago (MDW) → Madrid (MAD)
    1 Stop

    Fri Dec 20th 2024 Frontier Airlines · F9 2999 Depart at 2:15pm from Chicago (MDW) Fly for 2h 47m Arrive at 5:02pm in Dallas (DFW)

    Layover in Dallas for 5h 3m

    Fri Dec 20th 2024 Iberia Airlines · IB 364 Depart at 10:05pm from Dallas (DFW) Fly for 9h 20m Arrive at 2:25pm in Madrid (MAD)

    Book Flight Find Accommodations
@sarahbb1
Sarah Belizaire
@sarahbb1

Have flexible travel plans or looking for alternative routes given the chaos? Check out all the connection possibilities via a super helpful site created by @ismaelyws flightlist.io thanks to @andy_travels for the recommendation #travel #flights

@eyupitsjohn
John Ford
@eyupitsjohn

There seem to be lots of sites launching at the moment that promise to find you cheap flights but not many have the professional finish of Flightlist by @ismaelyws #travel #flights

@oamingsonaa
Roaming Sonaa
@roamingsonaa

For people wanting to maximize their trips, Flightlist is my newest travel hack for uncovering the coolest routes at irresistible prices. No stress, no annoying ads — just seamless flight booking with amazing functionality. It's designed for remote workers, backpackers, and people living abroad.

Read Sonaa's 7 Amazing Skyscanner Alternatives for Booking Travel
@andy_travels
ANDY TRAVELS
@andy_travels

@ismaelyws Just tried out Flightlist for the first time. Really nice idea, well made, and just what I need at the moment 👍

@travelwitbender
Travel With Bender
@travelwitbender

Did you spot my recent article about how to score cheap one way flights? ✈️ FlightList is my new secret tool for discovering cheap routes, within a departure date range. Plus you can also search by country/region for departures & destinations. Powerful! 💪

Read Josh's Ultimate Guide To Find Cheap One Way Flights
@travel.with.wes
Wesley Mergard
@travel.with.wes

One useful tool I've found for evaluating different departure and return dates is called FlightList.io. You can quickly scan different travel date ranges, carriers and one way flight options to easily determine the cheapest flight combinations for your trip.

Read Wesley's My Best Cheap Flight Hacks (Why Pay More?)

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FlightList Blog

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About FlightList

❝Founded by a remote worker and frequent flyer, who discovered that the best deals come from searching with flexible dates across entire countries or regions. Our streamlined platform strips away the clutter found on typical travel sites, offering a clean interface that focuses solely on finding cost-effective flights. Unlike traditional booking sites, FlightList allows users to search by date ranges and broad destinations, unveiling opportunities that rigid parameters often miss. Our filters let travelers tailor searches to their specific needs, whether they're digital nomads seeking their next adventure or budget-conscious explorers maximizing travel funds. We've made finding cheap flights into a quicker and easier experience, empowering users to discover just how far their budget can take them.❞

- Hans Desjarlais, Founder Hans Desjarlais Profile Picture