Penguin Hops

Cheap multi-city trips from Madrid — September 2026

Leave home, stay in several cities, and fly back — all in one loop. Penguin Hops searches a whole month to build these multi-city trips, the kind a point-to-point flight search won't show you.

9069 loop ideas start and end in Madrid in September 2026, with flights from 37 € total.

More filters
52 route ideas Madrid · September 2026 · 2 stops
Showing 1–20
Cheapest dates align
ES🇪🇸 Madrid → ES🇪🇸 Palma de Mallorca → ES🇪🇸 Seville → ES🇪🇸 Madrid
MAD -> PMI -> SVQ -> MAD
from 59.00 €
4h 10m total flight time
14-day trip
Madrid MAD → Palma de Mallorca PMI 2026-09-09
from 22.00 € Ryanair 1h 30m prices last checked on 2026-07-14
Book a stay in Palma de Mallorca: Booking.com | Hostelworld
Palma de Mallorca PMI → Seville SVQ 2026-09-16
from 15.00 € Ryanair 1h 35m prices last checked on 2026-07-14
Book a stay in Seville: Booking.com | Hostelworld
Seville SVQ → Madrid MAD 2026-09-23
from 22.00 € Iberia 1h 5m prices last checked on 2026-07-14
Cheapest-date itinerary
ES🇪🇸 Madrid → ES🇪🇸 Palma de Mallorca (2026-09-09) → ES🇪🇸 Seville (2026-09-16) → ES🇪🇸 Madrid (2026-09-23)
Cheapest dates align
ES🇪🇸 Madrid → RO🇷🇴 Timișoara → FR🇫🇷 Paris → ES🇪🇸 Madrid
MAD -> TSR -> BVA -> MAD
from 71.00 €
8h 10m total flight time
9-day trip
Madrid MAD → Timișoara TSR 2026-09-15
from 32.00 € Wizz Air 3h 25m prices last checked on 2026-07-14
Book a stay in Timișoara: Booking.com | Hostelworld
Timișoara TSR → Paris BVA 2026-09-21
from 19.00 € Wizz Air 2h 35m prices last checked on 2026-07-14
Book a stay in Paris: Booking.com | Hostelworld
Paris BVA → Madrid MAD 2026-09-24
from 20.00 € Ryanair 2h 10m prices last checked on 2026-07-14
Cheapest-date itinerary
ES🇪🇸 Madrid → RO🇷🇴 Timișoara (2026-09-15) → FR🇫🇷 Paris (2026-09-21) → ES🇪🇸 Madrid (2026-09-24)
Cheapest dates align
ES🇪🇸 Madrid → AT🇦🇹 Vienna → IE🇮🇪 Dublin → ES🇪🇸 Madrid
MAD -> VIE -> DUB -> MAD
from 85.00 €
8h 30m total flight time
8-day trip
Madrid MAD → Vienna VIE 2026-09-11
from 29.00 € Ryanair 3h prices last checked on 2026-07-14
Book a stay in Vienna: Booking.com | Hostelworld
Vienna VIE → Dublin DUB 2026-09-17
from 28.00 € Ryanair 2h 50m prices last checked on 2026-07-14
Book a stay in Dublin: Booking.com | Hostelworld
Dublin DUB → Madrid MAD 2026-09-19
from 28.00 € Ryanair 2h 40m prices last checked on 2026-07-14
Cheapest-date itinerary
ES🇪🇸 Madrid → AT🇦🇹 Vienna (2026-09-11) → IE🇮🇪 Dublin (2026-09-17) → ES🇪🇸 Madrid (2026-09-19)
Cheapest dates align
ES🇪🇸 Madrid → ES🇪🇸 Seville → IE🇮🇪 Dublin → ES🇪🇸 Madrid
MAD -> SVQ -> DUB -> MAD
from 87.00 €
6h 45m total flight time
16-day trip
Madrid MAD → Seville SVQ 2026-09-03
from 29.00 € Iberia Express 1h 10m prices last checked on 2026-07-14
Book a stay in Seville: Booking.com | Hostelworld
Seville SVQ → Dublin DUB 2026-09-11
from 30.00 € Ryanair 2h 55m prices last checked on 2026-07-14
Book a stay in Dublin: Booking.com | Hostelworld
Dublin DUB → Madrid MAD 2026-09-19
from 28.00 € Ryanair 2h 40m prices last checked on 2026-07-14
Cheapest-date itinerary
ES🇪🇸 Madrid → ES🇪🇸 Seville (2026-09-03) → IE🇮🇪 Dublin (2026-09-11) → ES🇪🇸 Madrid (2026-09-19)
Cheapest dates align
ES🇪🇸 Madrid → IT🇮🇹 Pisa → BG🇧🇬 Sofia → ES🇪🇸 Madrid
MAD -> PSA -> SOF -> MAD
from 100.00 €
8h 5m total flight time
11-day trip
Madrid MAD → Pisa PSA 2026-09-19
from 25.00 € Ryanair 2h 15m prices last checked on 2026-07-14
Book a stay in Pisa: Booking.com | Hostelworld
Pisa PSA → Sofia SOF 2026-09-24
from 39.00 € Ryanair 1h 55m prices last checked on 2026-07-14
Book a stay in Sofia: Booking.com | Hostelworld
Sofia SOF → Madrid MAD 2026-09-30
from 36.00 € Wizz Air 3h 55m prices last checked on 2026-07-14
Cheapest-date itinerary
ES🇪🇸 Madrid → IT🇮🇹 Pisa (2026-09-19) → BG🇧🇬 Sofia (2026-09-24) → ES🇪🇸 Madrid (2026-09-30)
Cheapest dates align
ES🇪🇸 Madrid → ES🇪🇸 Alicante → IE🇮🇪 Dublin → ES🇪🇸 Madrid
MAD -> ALC -> DUB -> MAD
from 103.00 €
6h 50m total flight time
17-day trip
Madrid MAD → Alicante ALC 2026-09-02
from 33.00 € Iberia 1h 15m prices last checked on 2026-07-14
Book a stay in Alicante: Booking.com | Hostelworld
Alicante ALC → Dublin DUB 2026-09-10
from 42.00 € Ryanair 2h 55m prices last checked on 2026-07-14
Book a stay in Dublin: Booking.com | Hostelworld
Dublin DUB → Madrid MAD 2026-09-19
from 28.00 € Ryanair 2h 40m prices last checked on 2026-07-14
Cheapest-date itinerary
ES🇪🇸 Madrid → ES🇪🇸 Alicante (2026-09-02) → IE🇮🇪 Dublin (2026-09-10) → ES🇪🇸 Madrid (2026-09-19)
Cheapest dates align
ES🇪🇸 Madrid → RO🇷🇴 Bucharest → MT🇲🇹 Malta → ES🇪🇸 Madrid
MAD -> OTP -> MLA -> MAD
from 107.00 €
8h 50m total flight time
6-day trip
Madrid MAD → Bucharest OTP 2026-09-24
from 46.00 € Wizz Air 3h 35m prices last checked on 2026-07-14
Book a stay in Bucharest: Booking.com | Hostelworld
Bucharest OTP → Malta MLA 2026-09-26
from 21.00 € Ryanair 2h 25m prices last checked on 2026-07-14
Book a stay in Malta: Booking.com | Hostelworld
Malta MLA → Madrid MAD 2026-09-30
from 40.00 € Ryanair 2h 50m prices last checked on 2026-07-14
Cheapest-date itinerary
ES🇪🇸 Madrid → RO🇷🇴 Bucharest (2026-09-24) → MT🇲🇹 Malta (2026-09-26) → ES🇪🇸 Madrid (2026-09-30)
Cheapest dates align
ES🇪🇸 Madrid → ES🇪🇸 Tenerife → FR🇫🇷 Paris → ES🇪🇸 Madrid
MAD -> TFS -> BVA -> MAD
from 107.00 €
9h 10m total flight time
8-day trip
Madrid MAD → Tenerife TFS 2026-09-16
from 56.00 € Iberia Express 3h prices last checked on 2026-07-14
Book a stay in Tenerife: Booking.com | Hostelworld
Tenerife TFS → Paris BVA 2026-09-21
from 31.00 € Ryanair 4h prices last checked on 2026-07-14
Book a stay in Paris: Booking.com | Hostelworld
Paris BVA → Madrid MAD 2026-09-24
from 20.00 € Ryanair 2h 10m prices last checked on 2026-07-14
Cheapest-date itinerary
ES🇪🇸 Madrid → ES🇪🇸 Tenerife (2026-09-16) → FR🇫🇷 Paris (2026-09-21) → ES🇪🇸 Madrid (2026-09-24)
Cheapest dates align
ES🇪🇸 Madrid → RS🇷🇸 Belgrade → ES🇪🇸 Alicante → ES🇪🇸 Madrid
MAD -> BEG -> ALC -> MAD
from 109.00 €
7h 35m total flight time
20-day trip
Madrid MAD → Belgrade BEG 2026-09-10
from 36.00 € Wizz Air 3h 10m prices last checked on 2026-07-14
Book a stay in Belgrade: Booking.com | Hostelworld
Belgrade BEG → Alicante ALC 2026-09-20
from 49.00 € Wizz Air 3h 10m prices last checked on 2026-07-14
Book a stay in Alicante: Booking.com | Hostelworld
Alicante ALC → Madrid MAD 2026-09-30
from 24.00 € Iberia 1h 15m prices last checked on 2026-07-14
Cheapest-date itinerary
ES🇪🇸 Madrid → RS🇷🇸 Belgrade (2026-09-10) → ES🇪🇸 Alicante (2026-09-20) → ES🇪🇸 Madrid (2026-09-30)
Cheapest dates align
ES🇪🇸 Madrid → IT🇮🇹 Pisa → GB🇬🇧 Manchester → ES🇪🇸 Madrid
MAD -> PSA -> MAN -> MAD
from 114.00 €
7h 25m total flight time
11-day trip
Madrid MAD → Pisa PSA 2026-09-19
from 25.00 € Ryanair 2h 15m prices last checked on 2026-07-14
Book a stay in Pisa: Booking.com | Hostelworld
Pisa PSA → Manchester MAN 2026-09-25
from 62.00 € Ryanair 2h 30m prices last checked on 2026-07-14
Book a stay in Manchester: Booking.com | Hostelworld
Manchester MAN → Madrid MAD 2026-09-30
from 27.00 € easyJet 2h 40m prices last checked on 2026-07-14
Cheapest-date itinerary
ES🇪🇸 Madrid → IT🇮🇹 Pisa (2026-09-19) → GB🇬🇧 Manchester (2026-09-25) → ES🇪🇸 Madrid (2026-09-30)
Cheapest dates align
ES🇪🇸 Madrid → AL🇦🇱 Tirana → ES🇪🇸 Palma de Mallorca → ES🇪🇸 Madrid
MAD -> TIA -> PMI -> MAD
from 118.00 €
9h 35m total flight time
13-day trip
Madrid MAD → Tirana TIA 2026-09-10
from 32.00 € Wizz Air 3h 10m prices last checked on 2026-07-14
Book a stay in Tirana: Booking.com | Hostelworld
Tirana TIA → Palma de Mallorca PMI 2026-09-18
from 71.00 € Air Serbia 4h 55m prices last checked on 2026-07-14
Book a stay in Palma de Mallorca: Booking.com | Hostelworld
Palma de Mallorca PMI → Madrid MAD 2026-09-23
from 15.00 € Ryanair 1h 30m prices last checked on 2026-07-14
Cheapest-date itinerary
ES🇪🇸 Madrid → AL🇦🇱 Tirana (2026-09-10) → ES🇪🇸 Palma de Mallorca (2026-09-18) → ES🇪🇸 Madrid (2026-09-23)
Cheapest dates align
ES🇪🇸 Madrid → RO🇷🇴 Bucharest → GB🇬🇧 Liverpool → ES🇪🇸 Madrid
MAD -> OTP -> LPL -> MAD
from 118.00 €
9h 50m total flight time
6-day trip
Madrid MAD → Bucharest OTP 2026-09-24
from 46.00 € Wizz Air 3h 35m prices last checked on 2026-07-14
Book a stay in Bucharest: Booking.com | Hostelworld
Bucharest OTP → Liverpool LPL 2026-09-27
from 48.00 € Wizz Air 3h 45m prices last checked on 2026-07-14
Book a stay in Liverpool: Booking.com | Hostelworld
Liverpool LPL → Madrid MAD 2026-09-30
from 24.00 € Ryanair 2h 30m prices last checked on 2026-07-14
Cheapest-date itinerary
ES🇪🇸 Madrid → RO🇷🇴 Bucharest (2026-09-24) → GB🇬🇧 Liverpool (2026-09-27) → ES🇪🇸 Madrid (2026-09-30)
Cheapest dates align
ES🇪🇸 Madrid → LT🇱🇹 Kaunas → ES🇪🇸 Palma de Mallorca → ES🇪🇸 Madrid
MAD -> KUN -> PMI -> MAD
from 119.00 €
9h total flight time
14-day trip
Madrid MAD → Kaunas KUN 2026-09-09
from 31.00 € Ryanair 3h 55m prices last checked on 2026-07-14
Book a stay in Kaunas: Booking.com | Hostelworld
Kaunas KUN → Palma de Mallorca PMI 2026-09-16
from 73.00 € Ryanair 3h 35m prices last checked on 2026-07-14
Book a stay in Palma de Mallorca: Booking.com | Hostelworld
Palma de Mallorca PMI → Madrid MAD 2026-09-23
from 15.00 € Ryanair 1h 30m prices last checked on 2026-07-14
Cheapest-date itinerary
ES🇪🇸 Madrid → LT🇱🇹 Kaunas (2026-09-09) → ES🇪🇸 Palma de Mallorca (2026-09-16) → ES🇪🇸 Madrid (2026-09-23)
Cheapest dates align
ES🇪🇸 Madrid → ES🇪🇸 Bilbao → ES🇪🇸 Barcelona → ES🇪🇸 Madrid
MAD -> BIO -> BCN -> MAD
from 121.00 €
3h 40m total flight time
20-day trip
Madrid MAD → Bilbao BIO 2026-09-09
from 43.00 € Iberia 1h 5m prices last checked on 2026-07-14
Book a stay in Bilbao: Booking.com | Hostelworld
Bilbao BIO → Barcelona BCN 2026-09-19
from 21.00 € Vueling 1h 10m prices last checked on 2026-07-14
Book a stay in Barcelona: Booking.com | Hostelworld
Barcelona BCN → Madrid MAD 2026-09-29
from 57.00 € Iberia 1h 25m prices last checked on 2026-07-14
Cheapest-date itinerary
ES🇪🇸 Madrid → ES🇪🇸 Bilbao (2026-09-09) → ES🇪🇸 Barcelona (2026-09-19) → ES🇪🇸 Madrid (2026-09-29)
Cheapest dates align
ES🇪🇸 Madrid → NO🇳🇴 Oslo → IT🇮🇹 Rome → ES🇪🇸 Madrid
MAD -> OSL -> FCO -> MAD
from 122.00 €
9h 30m total flight time
11-day trip
Madrid MAD → Oslo OSL 2026-09-03
from 54.00 € Norwegian 3h 30m prices last checked on 2026-07-14
Book a stay in Oslo: Booking.com | Hostelworld
Oslo OSL → Rome FCO 2026-09-10
from 38.00 € Wizz Air 3h 20m prices last checked on 2026-07-14
Book a stay in Rome: Booking.com | Hostelworld
Rome FCO → Madrid MAD 2026-09-14
from 30.00 € Wizz Air 2h 40m prices last checked on 2026-07-14
Cheapest-date itinerary
ES🇪🇸 Madrid → NO🇳🇴 Oslo (2026-09-03) → IT🇮🇹 Rome (2026-09-10) → ES🇪🇸 Madrid (2026-09-14)
Cheapest dates align
ES🇪🇸 Madrid → RO🇷🇴 Bucharest → GB🇬🇧 Birmingham → ES🇪🇸 Madrid
MAD -> OTP -> BHX -> MAD
from 124.00 €
9h 45m total flight time
6-day trip
Madrid MAD → Bucharest OTP 2026-09-24
from 46.00 € Wizz Air 3h 35m prices last checked on 2026-07-14
Book a stay in Bucharest: Booking.com | Hostelworld
Bucharest OTP → Birmingham BHX 2026-09-27
from 52.00 € Wizz Air 3h 40m prices last checked on 2026-07-14
Book a stay in Birmingham: Booking.com | Hostelworld
Birmingham BHX → Madrid MAD 2026-09-30
from 26.00 € Ryanair 2h 30m prices last checked on 2026-07-14
Cheapest-date itinerary
ES🇪🇸 Madrid → RO🇷🇴 Bucharest (2026-09-24) → GB🇬🇧 Birmingham (2026-09-27) → ES🇪🇸 Madrid (2026-09-30)
Cheapest dates align
ES🇪🇸 Madrid → IT🇮🇹 Milan → RO🇷🇴 Bucharest → ES🇪🇸 Madrid
MAD -> MXP -> OTP -> MAD
from 125.00 €
8h 40m total flight time
15-day trip
Madrid MAD → Milan MXP 2026-09-15
from 22.00 € Ryanair 2h 10m prices last checked on 2026-07-14
Book a stay in Milan: Booking.com | Hostelworld
Milan MXP → Bucharest OTP 2026-09-23
from 20.00 € Wizz Air 2h 25m prices last checked on 2026-07-14
Book a stay in Bucharest: Booking.com | Hostelworld
Bucharest OTP → Madrid MAD 2026-09-30
from 83.00 € Iberia 4h 5m prices last checked on 2026-07-14
Cheapest-date itinerary
ES🇪🇸 Madrid → IT🇮🇹 Milan (2026-09-15) → RO🇷🇴 Bucharest (2026-09-23) → ES🇪🇸 Madrid (2026-09-30)
Cheapest dates align
ES🇪🇸 Madrid → IT🇮🇹 Milan → IT🇮🇹 Catania → ES🇪🇸 Madrid
MAD -> MXP -> CTA -> MAD
from 129.00 €
7h 15m total flight time
15-day trip
Madrid MAD → Milan MXP 2026-09-15
from 22.00 € Ryanair 2h 10m prices last checked on 2026-07-14
Book a stay in Milan: Booking.com | Hostelworld
Milan MXP → Catania CTA 2026-09-23
from 18.00 € Ryanair 2h prices last checked on 2026-07-14
Book a stay in Catania: Booking.com | Hostelworld
Catania CTA → Madrid MAD 2026-09-30
from 89.00 € Ryanair 3h 5m prices last checked on 2026-07-14
Cheapest-date itinerary
ES🇪🇸 Madrid → IT🇮🇹 Milan (2026-09-15) → IT🇮🇹 Catania (2026-09-23) → ES🇪🇸 Madrid (2026-09-30)
Cheapest dates align
ES🇪🇸 Madrid → ES🇪🇸 Santa Cruz de La Palma → GB🇬🇧 Manchester → ES🇪🇸 Madrid
MAD -> SPC -> MAN -> MAD
from 130.00 €
10h 20m total flight time
4-day trip
Madrid MAD → Santa Cruz de La Palma SPC 2026-09-26
from 56.00 € Iberia Express 3h 5m prices last checked on 2026-07-14
Book a stay in Santa Cruz de La Palma: Booking.com | Hostelworld
Santa Cruz de La Palma SPC → Manchester MAN 2026-09-28
from 47.00 € Jet2 4h 35m prices last checked on 2026-07-14
Book a stay in Manchester: Booking.com | Hostelworld
Manchester MAN → Madrid MAD 2026-09-30
from 27.00 € easyJet 2h 40m prices last checked on 2026-07-14
Cheapest-date itinerary
ES🇪🇸 Madrid → ES🇪🇸 Santa Cruz de La Palma (2026-09-26) → GB🇬🇧 Manchester (2026-09-28) → ES🇪🇸 Madrid (2026-09-30)
Cheapest dates align
ES🇪🇸 Madrid → ES🇪🇸 Granada → PT🇵🇹 Faro → ES🇪🇸 Madrid
MAD -> GRX -> FAO -> MAD
from 134.00 €
17h 5m total flight time
13-day trip
Madrid MAD → Granada GRX 2026-09-09
from 34.00 € Iberia 1h 10m prices last checked on 2026-07-14
Book a stay in Granada: Booking.com | Hostelworld
Granada GRX → Faro FAO 2026-09-16
from 81.00 € Vueling 14h 35m prices last checked on 2026-07-14
Book a stay in Faro: Booking.com | Hostelworld
Faro FAO → Madrid MAD 2026-09-22
from 19.00 € Ryanair 1h 20m prices last checked on 2026-07-14
Cheapest-date itinerary
ES🇪🇸 Madrid → ES🇪🇸 Granada (2026-09-09) → PT🇵🇹 Faro (2026-09-16) → ES🇪🇸 Madrid (2026-09-22)
Prices marked "from X euros that month" are the cheapest fares observed that month; other dates may cost more.

Browse trips by starting city

Amsterdam Barcelona Belgrade Berlin Bremen Brussels Bucharest Budapest Cologne Copenhagen Dublin Eindhoven Frankfurt Hamburg Helsinki Innsbruck Kaunas Lisbon London Madrid Milan Munich Oslo Palma de Mallorca Paris Porto Prague Rome Sofia Stockholm Tirana Vienna Warsaw