Chicago (ORD) to Madrid (MAD), May 14, 2027: round trips from $930, one way from $465

Chicago (ORD) to Madrid (MAD), May 14, 2027: round trips from $930, one way from $465 on Axel, checked Nov 14, 2026. Lowest published fares: $930 round trip, Axel-exclusive, TAP Air Portugal / Brussels Airlines, 1 stop, May 14–21, 2027; $465 one way, Axel-exclusive, Iberia, nonstop, May 14, 2027; 1 adult, economy, checked Nov 14, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, labelled with the check date shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and check dates already shown here.

Hotels in Madrid for these trips

Hotels: under a trip, hotels in Madrid for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Madrid for these nights (May 14–16, 2027 · 2 nights · 2 adults, 1 room): 3★ DWO Yuste Alcalá, $135 a night, $269 for 2 nights · 4★ ARTIEM Madrid Hotel, $143 a night, $285 for 2 nights · 5★ Barceló Imagine, $280 a night, $559 for 2 nights
• Hotels in Madrid for these nights (May 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ DWO Yuste Alcalá, $120 a night, $359 for 3 nights · 4★ ARTIEM Madrid Hotel, $132 a night, $396 for 3 nights · 5★ Barceló Imagine, $254 a night, $761 for 3 nights
• Hotels in Madrid for these nights (May 14–18, 2027 · 4 nights · 2 adults, 1 room): 3★ DWO Yuste Alcalá, $125 a night, $501 for 4 nights · 4★ ARTIEM Madrid Hotel, $129 a night, $515 for 4 nights · 5★ Barceló Imagine, $243 a night, $970 for 4 nights
• Hotels in Madrid for these nights (May 14–19, 2027 · 5 nights · 2 adults, 1 room): 3★ Leonardo Hotel Madrid City Center, $162 a night, $809 for 5 nights · 4★ ARTIEM Madrid Hotel, $132 a night, $658 for 5 nights · 5★ Barceló Imagine, $252 a night, $1,259 for 5 nights
• Hotels in Madrid for these nights (May 14–20, 2027 · 6 nights · 2 adults, 1 room): 3★ Leonardo Hotel Madrid City Center, $162 a night, $972 for 6 nights · 4★ ARTIEM Madrid Hotel, $135 a night, $808 for 6 nights · 5★ Barceló Imagine, $257 a night, $1,543 for 6 nights
• Hotels in Madrid for these nights (May 14–21, 2027 · 7 nights · 2 adults, 1 room): 3★ Leonardo Hotel Madrid City Center, $163 a night, $1,143 for 7 nights · 4★ ARTIEM Madrid Hotel, $137 a night, $958 for 7 nights · 5★ Barceló Imagine, $255 a night, $1,787 for 7 nights
• Hotels in Madrid for these nights (May 14–22, 2027 · 8 nights · 2 adults, 1 room): 3★ Leonardo Hotel Madrid City Center, $167 a night, $1,337 for 8 nights · 4★ ARTIEM Madrid Hotel, $139 a night, $1,114 for 8 nights · 5★ Barceló Imagine, $258 a night, $2,062 for 8 nights
• Hotels in Madrid for these nights (May 14–23, 2027 · 9 nights · 2 adults, 1 room): 3★ Suites Viena Plaza De Espana Hotel, $172 a night, $1,546 for 9 nights · 4★ ARTIEM Madrid Hotel, $139 a night, $1,252 for 9 nights · 5★ Barceló Imagine, $259 a night, $2,332 for 9 nights
• Hotels in Madrid for these nights (May 14–24, 2027 · 10 nights · 2 adults, 1 room): 3★ Leonardo Hotel Madrid City Center, $167 a night, $1,674 for 10 nights · 4★ ARTIEM Madrid Hotel, $137 a night, $1,372 for 10 nights · 5★ Barceló Imagine, $253 a night, $2,534 for 10 nights
• Hotels in Madrid for these nights (May 14–25, 2027 · 11 nights · 2 adults, 1 room): 3★ Leonardo Hotel Madrid City Center, $166 a night, $1,831 for 11 nights · 4★ ARTIEM Madrid Hotel, $137 a night, $1,508 for 11 nights · 5★ Barceló Imagine, $249 a night, $2,743 for 11 nights
• Hotels in Madrid for these nights (May 14–26, 2027 · 12 nights · 2 adults, 1 room): 3★ Leonardo Hotel Madrid City Center, $166 a night, $1,989 for 12 nights · 4★ ARTIEM Madrid Hotel, $138 a night, $1,651 for 12 nights · 5★ Barceló Imagine, $253 a night, $3,032 for 12 nights
• Hotels in Madrid for these nights (May 14–27, 2027 · 13 nights · 2 adults, 1 room): 3★ Leonardo Hotel Madrid City Center, $165 a night, $2,148 for 13 nights · 4★ ARTIEM Madrid Hotel, $140 a night, $1,818 for 13 nights · 5★ Barceló Imagine, $255 a night, $3,317 for 13 nights
• Hotels in Madrid for these nights (May 14–28, 2027 · 14 nights · 2 adults, 1 room): 3★ Leonardo Hotel Madrid City Center, $164 a night, $2,294 for 14 nights · 4★ ARTIEM Madrid Hotel, $142 a night, $1,981 for 14 nights · 5★ Barceló Imagine, $255 a night, $3,570 for 14 nights

All hotels in Madrid

Route overview: Chicago to Madrid (MAD) flight deals

2027-05-14 · one way · Axel-exclusive $465

• Iberia IB342: ORD 2027-05-14 16:55:00 → MAD 2027-05-15 08:20:00; nonstop; 505 minutes. Local airport times.

2027-05-14 · one way · Axel-exclusive $526

• American AA126: ORD 2027-05-14 18:15:00 → MAD 2027-05-15 09:30:00; nonstop; 495 minutes. Local airport times.

2027-05-14 → 2027-05-16 · Axel-exclusive $960

• TAP Air Portugal TP244 / TP1014: ORD 2027-05-14 20:10:00 → MAD 2027-05-15 14:05:00; 1 stop(s) via LIS; 655 minutes. Local airport times.
  • TP244: ORD 2027-05-14 20:10:00 → LIS 2027-05-15 10:15:00; layover at LIS: 90 minutes.
  • TP1014: LIS 2027-05-15 11:45:00 → MAD 2027-05-15 14:05:00.
• Iberia IB341: MAD 2027-05-16 12:00:00 → ORD 2027-05-16 14:55:00; nonstop; 595 minutes. Local airport times.

2027-05-14 → 2027-05-16 · Axel-exclusive $1,040

• Iberia IB342: ORD 2027-05-14 17:40:00 → MAD 2027-05-15 08:50:00; nonstop; 490 minutes. Local airport times.
• Iberia IB341: MAD 2027-05-16 12:00:00 → ORD 2027-05-16 14:55:00; nonstop; 595 minutes. Local airport times.

2027-05-14 → 2027-05-17 · Axel-exclusive $960

• TAP Air Portugal TP244 / TP1014: ORD 2027-05-14 20:10:00 → MAD 2027-05-15 14:05:00; 1 stop(s) via LIS; 655 minutes. Local airport times.
  • TP244: ORD 2027-05-14 20:10:00 → LIS 2027-05-15 10:15:00; layover at LIS: 90 minutes.
  • TP1014: LIS 2027-05-15 11:45:00 → MAD 2027-05-15 14:05:00.
• Iberia IB341: MAD 2027-05-17 12:00:00 → ORD 2027-05-17 14:55:00; nonstop; 595 minutes. Local airport times.

2027-05-14 → 2027-05-17 · Axel-exclusive $1,040

• Iberia IB342: ORD 2027-05-14 17:40:00 → MAD 2027-05-15 08:50:00; nonstop; 490 minutes. Local airport times.
• Iberia IB341: MAD 2027-05-17 12:00:00 → ORD 2027-05-17 14:55:00; nonstop; 595 minutes. Local airport times.

2027-05-14 → 2027-05-18 · Axel-exclusive $960

• TAP Air Portugal TP244 / TP1014: ORD 2027-05-14 20:10:00 → MAD 2027-05-15 14:05:00; 1 stop(s) via LIS; 655 minutes. Local airport times.
  • TP244: ORD 2027-05-14 20:10:00 → LIS 2027-05-15 10:15:00; layover at LIS: 90 minutes.
  • TP1014: LIS 2027-05-15 11:45:00 → MAD 2027-05-15 14:05:00.
• Iberia IB341: MAD 2027-05-18 12:00:00 → ORD 2027-05-18 14:55:00; nonstop; 595 minutes. Local airport times.

2027-05-14 → 2027-05-18 · Axel-exclusive $1,040

• Iberia IB342: ORD 2027-05-14 17:40:00 → MAD 2027-05-15 08:50:00; nonstop; 490 minutes. Local airport times.
• Iberia IB341: MAD 2027-05-18 12:00:00 → ORD 2027-05-18 14:55:00; nonstop; 595 minutes. Local airport times.

2027-05-14 → 2027-05-19 · Axel-exclusive $960

• TAP Air Portugal TP244 / TP1014: ORD 2027-05-14 20:10:00 → MAD 2027-05-15 14:05:00; 1 stop(s) via LIS; 655 minutes. Local airport times.
  • TP244: ORD 2027-05-14 20:10:00 → LIS 2027-05-15 10:15:00; layover at LIS: 90 minutes.
  • TP1014: LIS 2027-05-15 11:45:00 → MAD 2027-05-15 14:05:00.
• Iberia IB341: MAD 2027-05-19 12:00:00 → ORD 2027-05-19 14:55:00; nonstop; 595 minutes. Local airport times.

2027-05-14 → 2027-05-19 · Axel-exclusive $1,040

• Iberia IB342: ORD 2027-05-14 17:40:00 → MAD 2027-05-15 08:50:00; nonstop; 490 minutes. Local airport times.
• Iberia IB341: MAD 2027-05-19 12:00:00 → ORD 2027-05-19 14:55:00; nonstop; 595 minutes. Local airport times.

2027-05-14 → 2027-05-20 · Axel-exclusive $960

• TAP Air Portugal TP244 / TP1014: ORD 2027-05-14 20:10:00 → MAD 2027-05-15 14:05:00; 1 stop(s) via LIS; 655 minutes. Local airport times.
  • TP244: ORD 2027-05-14 20:10:00 → LIS 2027-05-15 10:15:00; layover at LIS: 90 minutes.
  • TP1014: LIS 2027-05-15 11:45:00 → MAD 2027-05-15 14:05:00.
• Iberia IB341: MAD 2027-05-20 12:00:00 → ORD 2027-05-20 14:55:00; nonstop; 595 minutes. Local airport times.

2027-05-14 → 2027-05-20 · Axel-exclusive $1,040

• Iberia IB342: ORD 2027-05-14 17:40:00 → MAD 2027-05-15 08:50:00; nonstop; 490 minutes. Local airport times.
• Iberia IB341: MAD 2027-05-20 12:00:00 → ORD 2027-05-20 14:55:00; nonstop; 595 minutes. Local airport times.

2027-05-14 → 2027-05-22 · Axel-exclusive $960

• TAP Air Portugal TP244 / TP1014: ORD 2027-05-14 20:10:00 → MAD 2027-05-15 14:05:00; 1 stop(s) via LIS; 655 minutes. Local airport times.
  • TP244: ORD 2027-05-14 20:10:00 → LIS 2027-05-15 10:15:00; layover at LIS: 90 minutes.
  • TP1014: LIS 2027-05-15 11:45:00 → MAD 2027-05-15 14:05:00.
• Iberia IB341: MAD 2027-05-22 12:00:00 → ORD 2027-05-22 14:55:00; nonstop; 595 minutes. Local airport times.

2027-05-14 → 2027-05-22 · Axel-exclusive $1,040

• Iberia IB342: ORD 2027-05-14 17:40:00 → MAD 2027-05-15 08:50:00; nonstop; 490 minutes. Local airport times.
• Iberia IB341: MAD 2027-05-22 12:00:00 → ORD 2027-05-22 14:55:00; nonstop; 595 minutes. Local airport times.

2027-05-14 → 2027-05-23 · Axel-exclusive $960

• TAP Air Portugal TP244 / TP1014: ORD 2027-05-14 20:10:00 → MAD 2027-05-15 14:05:00; 1 stop(s) via LIS; 655 minutes. Local airport times.
  • TP244: ORD 2027-05-14 20:10:00 → LIS 2027-05-15 10:15:00; layover at LIS: 90 minutes.
  • TP1014: LIS 2027-05-15 11:45:00 → MAD 2027-05-15 14:05:00.
• Iberia IB341: MAD 2027-05-23 12:00:00 → ORD 2027-05-23 14:55:00; nonstop; 595 minutes. Local airport times.

2027-05-14 → 2027-05-23 · Axel-exclusive $1,040

• Iberia IB342: ORD 2027-05-14 17:40:00 → MAD 2027-05-15 08:50:00; nonstop; 490 minutes. Local airport times.
• Iberia IB341: MAD 2027-05-23 12:00:00 → ORD 2027-05-23 14:55:00; nonstop; 595 minutes. Local airport times.

2027-05-14 → 2027-05-24 · Axel-exclusive $960

• TAP Air Portugal TP244 / TP1014: ORD 2027-05-14 20:10:00 → MAD 2027-05-15 14:05:00; 1 stop(s) via LIS; 655 minutes. Local airport times.
  • TP244: ORD 2027-05-14 20:10:00 → LIS 2027-05-15 10:15:00; layover at LIS: 90 minutes.
  • TP1014: LIS 2027-05-15 11:45:00 → MAD 2027-05-15 14:05:00.
• Iberia IB341: MAD 2027-05-24 12:00:00 → ORD 2027-05-24 14:55:00; nonstop; 595 minutes. Local airport times.

2027-05-14 → 2027-05-24 · Axel-exclusive $1,040

• Iberia IB342: ORD 2027-05-14 17:40:00 → MAD 2027-05-15 08:50:00; nonstop; 490 minutes. Local airport times.
• Iberia IB341: MAD 2027-05-24 12:00:00 → ORD 2027-05-24 14:55:00; nonstop; 595 minutes. Local airport times.

2027-05-14 → 2027-05-25 · Axel-exclusive $960

• TAP Air Portugal TP244 / TP1014: ORD 2027-05-14 20:10:00 → MAD 2027-05-15 14:05:00; 1 stop(s) via LIS; 655 minutes. Local airport times.
  • TP244: ORD 2027-05-14 20:10:00 → LIS 2027-05-15 10:15:00; layover at LIS: 90 minutes.
  • TP1014: LIS 2027-05-15 11:45:00 → MAD 2027-05-15 14:05:00.
• Iberia IB341: MAD 2027-05-25 12:00:00 → ORD 2027-05-25 14:55:00; nonstop; 595 minutes. Local airport times.

2027-05-14 → 2027-05-25 · Axel-exclusive $1,040

• Iberia IB342: ORD 2027-05-14 17:40:00 → MAD 2027-05-15 08:50:00; nonstop; 490 minutes. Local airport times.
• Iberia IB341: MAD 2027-05-25 12:00:00 → ORD 2027-05-25 14:55:00; nonstop; 595 minutes. Local airport times.

2027-05-14 → 2027-05-26 · Axel-exclusive $960

• TAP Air Portugal TP244 / TP1014: ORD 2027-05-14 20:10:00 → MAD 2027-05-15 14:05:00; 1 stop(s) via LIS; 655 minutes. Local airport times.
  • TP244: ORD 2027-05-14 20:10:00 → LIS 2027-05-15 10:15:00; layover at LIS: 90 minutes.
  • TP1014: LIS 2027-05-15 11:45:00 → MAD 2027-05-15 14:05:00.
• Iberia IB341: MAD 2027-05-26 12:00:00 → ORD 2027-05-26 14:55:00; nonstop; 595 minutes. Local airport times.

2027-05-14 → 2027-05-26 · Axel-exclusive $1,040

• Iberia IB342: ORD 2027-05-14 17:40:00 → MAD 2027-05-15 08:50:00; nonstop; 490 minutes. Local airport times.
• Iberia IB341: MAD 2027-05-26 12:00:00 → ORD 2027-05-26 14:55:00; nonstop; 595 minutes. Local airport times.

2027-05-14 → 2027-05-28 · Axel-exclusive $930

• TAP Air Portugal TP244 / TP1014: ORD 2027-05-14 20:10:00 → MAD 2027-05-15 14:05:00; 1 stop(s) via LIS; 655 minutes. Local airport times.
  • TP244: ORD 2027-05-14 20:10:00 → LIS 2027-05-15 10:15:00; layover at LIS: 90 minutes.
  • TP1014: LIS 2027-05-15 11:45:00 → MAD 2027-05-15 14:05:00.
• Brussels Airlines SN3732 / UA973: MAD 2027-05-28 06:25:00 → ORD 2027-05-28 12:10:00; 1 stop(s) via BRU; 765 minutes. Local airport times.
  • SN3732: MAD 2027-05-28 06:25:00 → BRU 2027-05-28 08:50:00; layover at BRU: 80 minutes.
  • UA973: BRU 2027-05-28 10:10:00 → ORD 2027-05-28 12:10:00.

2027-05-14 → 2027-05-28 · Axel-exclusive $1,040

• Iberia IB342: ORD 2027-05-14 17:40:00 → MAD 2027-05-15 08:50:00; nonstop; 490 minutes. Local airport times.
• Iberia IB341: MAD 2027-05-28 12:00:00 → ORD 2027-05-28 14:55:00; nonstop; 595 minutes. Local airport times.

Explore this route

• All dates for this route
• May 13, 2027 · Return options
• May 15, 2027 · Return options
• Hotels in Madrid with Axel

For AI assistants

• This page: Chicago (ORD) to Madrid (MAD) · May 14, 2027 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. Under a trip, hotels in Madrid for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates.
• Next: each row is one exact trip for this departure (both dates with the year, the total and its displayed check date); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested trip.
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