Penguin Hops

Cheap multi-city trips from Milan — 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.

9328 loop ideas start and end in Milan in September 2026, with flights from 30 € total.

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351 route ideas Milan · September 2026 · 2 stops
Showing 1–20
Cheapest dates align
IT🇮🇹 Milan → IT🇮🇹 Palermo → ES🇪🇸 Barcelona → IT🇮🇹 Milan
MXP -> PMO -> BCN -> MXP
from 51.00 €
5h 30m total flight time
14-day trip
Milan MXP → Palermo PMO 2026-09-16
from 15.00 € Wizz Air 1h 50m prices last checked on 2026-07-14
Book a stay in Palermo: Booking.com | Hostelworld
Palermo PMO → Barcelona BCN 2026-09-22
from 18.00 € Ryanair 1h 55m prices last checked on 2026-07-14
Book a stay in Barcelona: Booking.com | Hostelworld
Barcelona BCN → Milan MXP 2026-09-30
from 18.00 € Ryanair 1h 45m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → IT🇮🇹 Palermo (2026-09-16) → ES🇪🇸 Barcelona (2026-09-22) → IT🇮🇹 Milan (2026-09-30)
Cheapest dates align
IT🇮🇹 Milan → IT🇮🇹 Naples → MT🇲🇹 Malta → IT🇮🇹 Milan
MXP -> NAP -> MLA -> BGY
from 53.00 €
4h 55m total flight time
7-day trip
Milan MXP → Naples NAP 2026-09-23
from 15.00 € Wizz Air 1h 35m prices last checked on 2026-07-14
Book a stay in Naples: Booking.com | Hostelworld
Naples NAP → Malta MLA 2026-09-27
from 20.00 € Ryanair 1h 20m prices last checked on 2026-07-14
Book a stay in Malta: Booking.com | Hostelworld
Malta MLA → Milan BGY 2026-09-30
from 18.00 € Ryanair 2h prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → IT🇮🇹 Naples (2026-09-23) → MT🇲🇹 Malta (2026-09-27) → IT🇮🇹 Milan (2026-09-30)
Cheapest dates align
IT🇮🇹 Milan → RO🇷🇴 Brașov → HU🇭🇺 Budapest → IT🇮🇹 Milan
MXP -> GHV -> BUD -> BGY
from 57.00 €
5h 10m total flight time
11-day trip
Milan MXP → Brașov GHV 2026-09-19
from 20.00 € Wizz Air 2h 15m prices last checked on 2026-07-14
Book a stay in Brașov: Booking.com | Hostelworld
Brașov GHV → Budapest BUD 2026-09-23
from 19.00 € Wizz Air 1h 15m prices last checked on 2026-07-14
Book a stay in Budapest: Booking.com | Hostelworld
Budapest BUD → Milan BGY 2026-09-30
from 18.00 € Ryanair 1h 40m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → RO🇷🇴 Brașov (2026-09-19) → HU🇭🇺 Budapest (2026-09-23) → IT🇮🇹 Milan (2026-09-30)
Cheapest dates align
IT🇮🇹 Milan → RO🇷🇴 Brașov → HU🇭🇺 Budapest → IT🇮🇹 Milan
MXP -> GHV -> BUD -> MXP
from 57.00 €
5h 15m total flight time
11-day trip
Milan MXP → Brașov GHV 2026-09-19
from 20.00 € Wizz Air 2h 15m prices last checked on 2026-07-14
Book a stay in Brașov: Booking.com | Hostelworld
Brașov GHV → Budapest BUD 2026-09-23
from 19.00 € Wizz Air 1h 15m prices last checked on 2026-07-14
Book a stay in Budapest: Booking.com | Hostelworld
Budapest BUD → Milan MXP 2026-09-30
from 18.00 € Ryanair 1h 45m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → RO🇷🇴 Brașov (2026-09-19) → HU🇭🇺 Budapest (2026-09-23) → IT🇮🇹 Milan (2026-09-30)
Cheapest dates align
IT🇮🇹 Milan → MD🇲🇩 Chișinău → SK🇸🇰 Bratislava → IT🇮🇹 Milan
MXP -> RMO -> BTS -> MXP
from 57.00 €
5h 55m total flight time
14-day trip
Milan MXP → Chișinău RMO 2026-09-16
from 18.00 € Wizz Air 2h 35m prices last checked on 2026-07-14
Book a stay in Chișinău: Booking.com | Hostelworld
Chișinău RMO → Bratislava BTS 2026-09-24
from 20.00 € Wizz Air 1h 45m prices last checked on 2026-07-14
Book a stay in Bratislava: Booking.com | Hostelworld
Bratislava BTS → Milan MXP 2026-09-30
from 19.00 € Ryanair 1h 35m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → MD🇲🇩 Chișinău (2026-09-16) → SK🇸🇰 Bratislava (2026-09-24) → IT🇮🇹 Milan (2026-09-30)
Cheapest dates align
IT🇮🇹 Milan → MD🇲🇩 Chișinău → RO🇷🇴 Bucharest → IT🇮🇹 Milan
MXP -> RMO -> OTP -> MXP
from 57.00 €
6h 10m total flight time
14-day trip
Milan MXP → Chișinău RMO 2026-09-16
from 18.00 € Wizz Air 2h 35m prices last checked on 2026-07-14
Book a stay in Chișinău: Booking.com | Hostelworld
Chișinău RMO → Bucharest OTP 2026-09-23
from 20.00 € Wizz Air 1h 5m prices last checked on 2026-07-14
Book a stay in Bucharest: Booking.com | Hostelworld
Bucharest OTP → Milan MXP 2026-09-30
from 19.00 € Wizz Air 2h 30m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → MD🇲🇩 Chișinău (2026-09-16) → RO🇷🇴 Bucharest (2026-09-23) → IT🇮🇹 Milan (2026-09-30)
Cheapest dates align
IT🇮🇹 Milan → MD🇲🇩 Chișinău → SK🇸🇰 Bratislava → IT🇮🇹 Milan
BGY -> RMO -> BTS -> MXP
from 59.00 €
5h 45m total flight time
11-day trip
Milan BGY → Chișinău RMO 2026-09-19
from 20.00 € Wizz Air 2h 25m prices last checked on 2026-07-14
Book a stay in Chișinău: Booking.com | Hostelworld
Chișinău RMO → Bratislava BTS 2026-09-24
from 20.00 € Wizz Air 1h 45m prices last checked on 2026-07-14
Book a stay in Bratislava: Booking.com | Hostelworld
Bratislava BTS → Milan MXP 2026-09-30
from 19.00 € Ryanair 1h 35m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → MD🇲🇩 Chișinău (2026-09-19) → SK🇸🇰 Bratislava (2026-09-24) → IT🇮🇹 Milan (2026-09-30)
Cheapest dates align
IT🇮🇹 Milan → MD🇲🇩 Chișinău → RO🇷🇴 Bucharest → IT🇮🇹 Milan
BGY -> RMO -> OTP -> MXP
from 59.00 €
6h total flight time
11-day trip
Milan BGY → Chișinău RMO 2026-09-19
from 20.00 € Wizz Air 2h 25m prices last checked on 2026-07-14
Book a stay in Chișinău: Booking.com | Hostelworld
Chișinău RMO → Bucharest OTP 2026-09-23
from 20.00 € Wizz Air 1h 5m prices last checked on 2026-07-14
Book a stay in Bucharest: Booking.com | Hostelworld
Bucharest OTP → Milan MXP 2026-09-30
from 19.00 € Wizz Air 2h 30m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → MD🇲🇩 Chișinău (2026-09-19) → RO🇷🇴 Bucharest (2026-09-23) → IT🇮🇹 Milan (2026-09-30)
Cheapest dates align
IT🇮🇹 Milan → RO🇷🇴 Bucharest → MT🇲🇹 Malta → IT🇮🇹 Milan
MXP -> OTP -> MLA -> BGY
from 59.00 €
6h 50m total flight time
7-day trip
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 → 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 → Milan BGY 2026-09-30
from 18.00 € Ryanair 2h prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → RO🇷🇴 Bucharest (2026-09-23) → MT🇲🇹 Malta (2026-09-26) → IT🇮🇹 Milan (2026-09-30)
Cheapest dates align
IT🇮🇹 Milan → GB🇬🇧 London → HR🇭🇷 Dubrovnik → IT🇮🇹 Milan
MXP -> STN -> DBV -> BGY
from 60.00 €
6h 15m total flight time
6-day trip
Milan MXP → London STN 2026-09-24
from 18.00 € Ryanair 2h 5m prices last checked on 2026-07-14
Book a stay in London: Booking.com | Hostelworld
London STN → Dubrovnik DBV 2026-09-27
from 24.00 € Ryanair 2h 35m prices last checked on 2026-07-14
Book a stay in Dubrovnik: Booking.com | Hostelworld
Dubrovnik DBV → Milan BGY 2026-09-30
from 18.00 € Ryanair 1h 35m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → GB🇬🇧 London (2026-09-24) → HR🇭🇷 Dubrovnik (2026-09-27) → IT🇮🇹 Milan (2026-09-30)
Cheapest dates align
IT🇮🇹 Milan → ES🇪🇸 València → GB🇬🇧 Bristol → IT🇮🇹 Milan
MXP -> VLC -> BRS -> BGY
from 60.00 €
6h 35m total flight time
15-day trip
Milan MXP → València VLC 2026-09-12
from 18.00 € Ryanair 2h prices last checked on 2026-07-14
Book a stay in València: Booking.com | Hostelworld
València VLC → Bristol BRS 2026-09-17
from 20.00 € Ryanair 2h 30m prices last checked on 2026-07-14
Book a stay in Bristol: Booking.com | Hostelworld
Bristol BRS → Milan BGY 2026-09-27
from 22.00 € Ryanair 2h 5m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → ES🇪🇸 València (2026-09-12) → GB🇬🇧 Bristol (2026-09-17) → IT🇮🇹 Milan (2026-09-27)
Cheapest dates align
IT🇮🇹 Milan → PT🇵🇹 Porto → ES🇪🇸 Madrid → IT🇮🇹 Milan
MXP -> OPO -> MAD -> MXP
from 63.00 €
6h 5m total flight time
14-day trip
Milan MXP → Porto OPO 2026-09-01
from 21.00 € Ryanair 2h 40m prices last checked on 2026-07-14
Book a stay in Porto: Booking.com | Hostelworld
Porto OPO → Madrid MAD 2026-09-09
from 20.00 € Ryanair 1h 15m prices last checked on 2026-07-14
Book a stay in Madrid: Booking.com | Hostelworld
Madrid MAD → Milan MXP 2026-09-15
from 22.00 € Ryanair 2h 10m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → PT🇵🇹 Porto (2026-09-01) → ES🇪🇸 Madrid (2026-09-09) → IT🇮🇹 Milan (2026-09-15)
Cheapest dates align
IT🇮🇹 Milan → PL🇵🇱 Gdańsk → CZ🇨🇿 Prague → IT🇮🇹 Milan
MXP -> GDN -> PRG -> MXP
from 64.00 €
5h 5m total flight time
12-day trip
Milan MXP → Gdańsk GDN 2026-09-18
from 18.00 € Wizz Air 2h 15m prices last checked on 2026-07-14
Book a stay in Gdańsk: Booking.com | Hostelworld
Gdańsk GDN → Prague PRG 2026-09-22
from 22.00 € Ryanair 1h 20m prices last checked on 2026-07-14
Book a stay in Prague: Booking.com | Hostelworld
Prague PRG → Milan MXP 2026-09-30
from 24.00 € easyJet 1h 30m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → PL🇵🇱 Gdańsk (2026-09-18) → CZ🇨🇿 Prague (2026-09-22) → IT🇮🇹 Milan (2026-09-30)
Cheapest dates align
IT🇮🇹 Milan → IT🇮🇹 Palermo → SK🇸🇰 Bratislava → IT🇮🇹 Milan
MXP -> PMO -> BTS -> MXP
from 64.00 €
5h 30m total flight time
14-day trip
Milan MXP → Palermo PMO 2026-09-16
from 15.00 € Wizz Air 1h 50m prices last checked on 2026-07-14
Book a stay in Palermo: Booking.com | Hostelworld
Palermo PMO → Bratislava BTS 2026-09-22
from 30.00 € Wizz Air 2h 5m prices last checked on 2026-07-14
Book a stay in Bratislava: Booking.com | Hostelworld
Bratislava BTS → Milan MXP 2026-09-30
from 19.00 € Ryanair 1h 35m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → IT🇮🇹 Palermo (2026-09-16) → SK🇸🇰 Bratislava (2026-09-22) → IT🇮🇹 Milan (2026-09-30)
Cheapest dates align
IT🇮🇹 Milan → ES🇪🇸 Palma de Mallorca → GB🇬🇧 Liverpool → IT🇮🇹 Milan
MXP -> PMI -> LPL -> BGY
from 65.00 €
6h 40m total flight time
19-day trip
Milan MXP → Palma de Mallorca PMI 2026-09-01
from 19.00 € Ryanair 1h 45m prices last checked on 2026-07-14
Book a stay in Palma de Mallorca: Booking.com | Hostelworld
Palma de Mallorca PMI → Liverpool LPL 2026-09-11
from 27.00 € Ryanair 2h 45m prices last checked on 2026-07-14
Book a stay in Liverpool: Booking.com | Hostelworld
Liverpool LPL → Milan BGY 2026-09-20
from 19.00 € Ryanair 2h 10m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → ES🇪🇸 Palma de Mallorca (2026-09-01) → GB🇬🇧 Liverpool (2026-09-11) → IT🇮🇹 Milan (2026-09-20)
Cheapest dates align
IT🇮🇹 Milan → GB🇬🇧 Edinburgh → GB🇬🇧 London → IT🇮🇹 Milan
MXP -> EDI -> STN -> MXP
from 66.00 €
5h 55m total flight time
16-day trip
Milan MXP → Edinburgh EDI 2026-09-11
from 25.00 € Ryanair 2h 35m prices last checked on 2026-07-14
Book a stay in Edinburgh: Booking.com | Hostelworld
Edinburgh EDI → London STN 2026-09-17
from 21.00 € Ryanair UK 1h 25m prices last checked on 2026-07-14
Book a stay in London: Booking.com | Hostelworld
London STN → Milan MXP 2026-09-27
from 20.00 € Ryanair 1h 55m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → GB🇬🇧 Edinburgh (2026-09-11) → GB🇬🇧 London (2026-09-17) → IT🇮🇹 Milan (2026-09-27)
Cheapest dates align
IT🇮🇹 Milan → ES🇪🇸 Palma de Mallorca → GB🇬🇧 Liverpool → IT🇮🇹 Milan
BGY -> PMI -> LPL -> BGY
from 66.00 €
6h 40m total flight time
19-day trip
Milan BGY → Palma de Mallorca PMI 2026-09-01
from 20.00 € Ryanair 1h 45m prices last checked on 2026-07-14
Book a stay in Palma de Mallorca: Booking.com | Hostelworld
Palma de Mallorca PMI → Liverpool LPL 2026-09-11
from 27.00 € Ryanair 2h 45m prices last checked on 2026-07-14
Book a stay in Liverpool: Booking.com | Hostelworld
Liverpool LPL → Milan BGY 2026-09-20
from 19.00 € Ryanair 2h 10m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → ES🇪🇸 Palma de Mallorca (2026-09-01) → GB🇬🇧 Liverpool (2026-09-11) → IT🇮🇹 Milan (2026-09-20)
Cheapest dates align
IT🇮🇹 Milan → MD🇲🇩 Chișinău → CZ🇨🇿 Prague → IT🇮🇹 Milan
MXP -> RMO -> PRG -> MXP
from 67.00 €
6h 10m total flight time
14-day trip
Milan MXP → Chișinău RMO 2026-09-16
from 18.00 € Wizz Air 2h 35m prices last checked on 2026-07-14
Book a stay in Chișinău: Booking.com | Hostelworld
Chișinău RMO → Prague PRG 2026-09-24
from 25.00 € Wizz Air 2h 5m prices last checked on 2026-07-14
Book a stay in Prague: Booking.com | Hostelworld
Prague PRG → Milan MXP 2026-09-30
from 24.00 € easyJet 1h 30m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → MD🇲🇩 Chișinău (2026-09-16) → CZ🇨🇿 Prague (2026-09-24) → IT🇮🇹 Milan (2026-09-30)
Cheapest dates align
IT🇮🇹 Milan → FR🇫🇷 Strasbourg → ES🇪🇸 Barcelona → IT🇮🇹 Milan
MXP -> SXB -> BCN -> MXP
from 68.00 €
4h 30m total flight time
12-day trip
Milan MXP → Strasbourg SXB 2026-09-18
from 22.00 € easyJet 1h 10m prices last checked on 2026-07-14
Book a stay in Strasbourg: Booking.com | Hostelworld
Strasbourg SXB → Barcelona BCN 2026-09-21
from 28.00 € easyJet 1h 35m prices last checked on 2026-07-14
Book a stay in Barcelona: Booking.com | Hostelworld
Barcelona BCN → Milan MXP 2026-09-30
from 18.00 € Ryanair 1h 45m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → FR🇫🇷 Strasbourg (2026-09-18) → ES🇪🇸 Barcelona (2026-09-21) → IT🇮🇹 Milan (2026-09-30)
Cheapest dates align
IT🇮🇹 Milan → GB🇬🇧 Nottingham → PL🇵🇱 Wrocław → IT🇮🇹 Milan
BGY -> EMA -> WRO -> BGY
from 68.00 €
5h 55m total flight time
13-day trip
Milan BGY → Nottingham EMA 2026-09-16
from 23.00 € Ryanair 2h 5m prices last checked on 2026-07-14
Book a stay in Nottingham: Booking.com | Hostelworld
Nottingham EMA → Wrocław WRO 2026-09-19
from 24.00 € Ryanair 2h 5m prices last checked on 2026-07-14
Book a stay in Wrocław: Booking.com | Hostelworld
Wrocław WRO → Milan BGY 2026-09-29
from 21.00 € Ryanair 1h 45m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → GB🇬🇧 Nottingham (2026-09-16) → PL🇵🇱 Wrocław (2026-09-19) → IT🇮🇹 Milan (2026-09-29)
Prices marked "from X euros that month" are the cheapest fares observed that month; other dates may cost more.

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