Penguin Hops

Cheap multi-city trips from Milan

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.

9284 loop ideas start and end in Milan in October 2026, with flights from 30 € total.

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491 route ideas Milan · October 2026 · 2 stops
Showing 1–20
Cheapest dates align
IT🇮🇹 Milan → MD🇲🇩 Chișinău → BG🇧🇬 Sofia → IT🇮🇹 Milan
MXP -> RMO -> SOF -> BGY
from 48.00 €
6h 20m total flight time
14-day trip
Milan MXP → Chișinău RMO 2026-10-14
from 18.00 € Wizz Air 2h 35m prices last checked on 2026-07-14
Book a stay in Chișinău: Booking.com | Hostelworld
Chișinău RMO → Sofia SOF 2026-10-21
from 15.00 € Wizz Air 1h 30m prices last checked on 2026-07-14
Book a stay in Sofia: Booking.com | Hostelworld
Sofia SOF → Milan BGY 2026-10-28
from 15.00 € Wizz Air 2h 15m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → MD🇲🇩 Chișinău (2026-10-14) → BG🇧🇬 Sofia (2026-10-21) → IT🇮🇹 Milan (2026-10-28)
Cheapest dates align
IT🇮🇹 Milan → PL🇵🇱 Kraków → PL🇵🇱 Gdańsk → IT🇮🇹 Milan
BGY -> KRK -> GDN -> MXP
from 50.00 €
5h 10m total flight time
14-day trip
Milan BGY → Kraków KRK 2026-10-14
from 18.00 € Ryanair 1h 45m prices last checked on 2026-07-14
Book a stay in Kraków: Booking.com | Hostelworld
Kraków KRK → Gdańsk GDN 2026-10-22
from 16.00 € Ryanair 1h 10m prices last checked on 2026-07-14
Book a stay in Gdańsk: Booking.com | Hostelworld
Gdańsk GDN → Milan MXP 2026-10-28
from 16.00 € Wizz Air 2h 15m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → PL🇵🇱 Kraków (2026-10-14) → PL🇵🇱 Gdańsk (2026-10-22) → IT🇮🇹 Milan (2026-10-28)
Cheapest dates align
IT🇮🇹 Milan → MD🇲🇩 Chișinău → BG🇧🇬 Sofia → IT🇮🇹 Milan
BGY -> RMO -> SOF -> BGY
from 50.00 €
6h 10m total flight time
11-day trip
Milan BGY → Chișinău RMO 2026-10-17
from 20.00 € Wizz Air 2h 25m prices last checked on 2026-07-14
Book a stay in Chișinău: Booking.com | Hostelworld
Chișinău RMO → Sofia SOF 2026-10-21
from 15.00 € Wizz Air 1h 30m prices last checked on 2026-07-14
Book a stay in Sofia: Booking.com | Hostelworld
Sofia SOF → Milan BGY 2026-10-28
from 15.00 € Wizz Air 2h 15m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → MD🇲🇩 Chișinău (2026-10-17) → BG🇧🇬 Sofia (2026-10-21) → IT🇮🇹 Milan (2026-10-28)
Cheapest dates align
IT🇮🇹 Milan → IT🇮🇹 Catania → IT🇮🇹 Naples → IT🇮🇹 Milan
MXP -> CTA -> NAP -> MXP
from 53.00 €
4h 50m total flight time
14-day trip
Milan MXP → Catania CTA 2026-10-07
from 18.00 € Ryanair 2h prices last checked on 2026-07-14
Book a stay in Catania: Booking.com | Hostelworld
Catania CTA → Naples NAP 2026-10-14
from 20.00 € Ryanair 1h 10m prices last checked on 2026-07-14
Book a stay in Naples: Booking.com | Hostelworld
Naples NAP → Milan MXP 2026-10-21
from 15.00 € Wizz Air 1h 40m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → IT🇮🇹 Catania (2026-10-07) → IT🇮🇹 Naples (2026-10-14) → IT🇮🇹 Milan (2026-10-21)
Cheapest dates align
IT🇮🇹 Milan → PL🇵🇱 Katowice → RO🇷🇴 Brașov → IT🇮🇹 Milan
BGY -> KTW -> GHV -> MXP
from 54.00 €
5h 35m total flight time
17-day trip
Milan BGY → Katowice KTW 2026-10-14
from 19.00 € Ryanair 1h 45m prices last checked on 2026-07-14
Book a stay in Katowice: Booking.com | Hostelworld
Katowice KTW → Brașov GHV 2026-10-24
from 16.00 € Wizz Air 1h 25m prices last checked on 2026-07-14
Book a stay in Brașov: Booking.com | Hostelworld
Brașov GHV → Milan MXP 2026-10-31
from 19.00 € Wizz Air 2h 25m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → PL🇵🇱 Katowice (2026-10-14) → RO🇷🇴 Brașov (2026-10-24) → IT🇮🇹 Milan (2026-10-31)
Cheapest dates align
IT🇮🇹 Milan → IT🇮🇹 Naples → BG🇧🇬 Sofia → IT🇮🇹 Milan
MXP -> NAP -> SOF -> BGY
from 55.00 €
5h 35m total flight time
14-day trip
Milan MXP → Naples NAP 2026-10-14
from 15.00 € Wizz Air 1h 35m prices last checked on 2026-07-14
Book a stay in Naples: Booking.com | Hostelworld
Naples NAP → Sofia SOF 2026-10-20
from 25.00 € Wizz Air 1h 45m prices last checked on 2026-07-14
Book a stay in Sofia: Booking.com | Hostelworld
Sofia SOF → Milan BGY 2026-10-28
from 15.00 € Wizz Air 2h 15m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → IT🇮🇹 Naples (2026-10-14) → BG🇧🇬 Sofia (2026-10-20) → IT🇮🇹 Milan (2026-10-28)
Cheapest dates align
IT🇮🇹 Milan → FR🇫🇷 Paris → ES🇪🇸 Barcelona → IT🇮🇹 Milan
BGY -> BVA -> BCN -> MXP
from 56.00 €
5h total flight time
6-day trip
Milan BGY → Paris BVA 2026-10-01
from 20.00 € Ryanair 1h 35m prices last checked on 2026-07-14
Book a stay in Paris: Booking.com | Hostelworld
Paris BVA → Barcelona BCN 2026-10-04
from 20.00 € Ryanair 1h 45m prices last checked on 2026-07-14
Book a stay in Barcelona: Booking.com | Hostelworld
Barcelona BCN → Milan MXP 2026-10-07
from 16.00 € Vueling 1h 40m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → FR🇫🇷 Paris (2026-10-01) → ES🇪🇸 Barcelona (2026-10-04) → IT🇮🇹 Milan (2026-10-07)
Cheapest dates align
IT🇮🇹 Milan → CZ🇨🇿 Prague → PL🇵🇱 Kraków → IT🇮🇹 Milan
MXP -> PRG -> KRK -> BGY
from 58.00 €
4h 25m total flight time
10-day trip
Milan MXP → Prague PRG 2026-10-11
from 19.00 € easyJet 1h 30m prices last checked on 2026-07-14
Book a stay in Prague: Booking.com | Hostelworld
Prague PRG → Kraków KRK 2026-10-17
from 21.00 € Ryanair 1h 10m prices last checked on 2026-07-14
Book a stay in Kraków: Booking.com | Hostelworld
Kraków KRK → Milan BGY 2026-10-21
from 18.00 € Ryanair 1h 45m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → CZ🇨🇿 Prague (2026-10-11) → PL🇵🇱 Kraków (2026-10-17) → IT🇮🇹 Milan (2026-10-21)
Cheapest dates align
IT🇮🇹 Milan → IT🇮🇹 Naples → RO🇷🇴 Brașov → IT🇮🇹 Milan
MXP -> NAP -> GHV -> MXP
from 58.00 €
6h 5m total flight time
17-day trip
Milan MXP → Naples NAP 2026-10-14
from 15.00 € Wizz Air 1h 35m prices last checked on 2026-07-14
Book a stay in Naples: Booking.com | Hostelworld
Naples NAP → Brașov GHV 2026-10-21
from 24.00 € Wizz Air 2h 5m prices last checked on 2026-07-14
Book a stay in Brașov: Booking.com | Hostelworld
Brașov GHV → Milan MXP 2026-10-31
from 19.00 € Wizz Air 2h 25m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → IT🇮🇹 Naples (2026-10-14) → RO🇷🇴 Brașov (2026-10-21) → IT🇮🇹 Milan (2026-10-31)
Cheapest dates align
IT🇮🇹 Milan → CZ🇨🇿 Prague → PL🇵🇱 Kraków → IT🇮🇹 Milan
MXP -> PRG -> KRK -> MXP
from 59.00 €
4h 35m total flight time
10-day trip
Milan MXP → Prague PRG 2026-10-11
from 19.00 € easyJet 1h 30m prices last checked on 2026-07-14
Book a stay in Prague: Booking.com | Hostelworld
Prague PRG → Kraków KRK 2026-10-17
from 21.00 € Ryanair 1h 10m prices last checked on 2026-07-14
Book a stay in Kraków: Booking.com | Hostelworld
Kraków KRK → Milan MXP 2026-10-21
from 19.00 € Wizz Air 1h 55m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → CZ🇨🇿 Prague (2026-10-11) → PL🇵🇱 Kraków (2026-10-17) → IT🇮🇹 Milan (2026-10-21)
Cheapest dates align
IT🇮🇹 Milan → IT🇮🇹 Bari → SK🇸🇰 Bratislava → IT🇮🇹 Milan
MXP -> BRI -> BTS -> MXP
from 59.00 €
4h 55m total flight time
10-day trip
Milan MXP → Bari BRI 2026-10-11
from 20.00 € Ryanair 1h 40m prices last checked on 2026-07-14
Book a stay in Bari: Booking.com | Hostelworld
Bari BRI → Bratislava BTS 2026-10-19
from 20.00 € Ryanair 1h 40m prices last checked on 2026-07-14
Book a stay in Bratislava: Booking.com | Hostelworld
Bratislava BTS → Milan MXP 2026-10-21
from 19.00 € Ryanair 1h 35m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → IT🇮🇹 Bari (2026-10-11) → SK🇸🇰 Bratislava (2026-10-19) → IT🇮🇹 Milan (2026-10-21)
Cheapest dates align
IT🇮🇹 Milan → HR🇭🇷 Dubrovnik → PL🇵🇱 Wrocław → IT🇮🇹 Milan
BGY -> DBV -> WRO -> BGY
from 59.00 €
5h 5m total flight time
11-day trip
Milan BGY → Dubrovnik DBV 2026-10-17
from 18.00 € Ryanair 1h 30m prices last checked on 2026-07-14
Book a stay in Dubrovnik: Booking.com | Hostelworld
Dubrovnik DBV → Wrocław WRO 2026-10-19
from 20.00 € Ryanair 1h 50m prices last checked on 2026-07-14
Book a stay in Wrocław: Booking.com | Hostelworld
Wrocław WRO → Milan BGY 2026-10-28
from 21.00 € Ryanair 1h 45m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → HR🇭🇷 Dubrovnik (2026-10-17) → PL🇵🇱 Wrocław (2026-10-19) → IT🇮🇹 Milan (2026-10-28)
Cheapest dates align
IT🇮🇹 Milan → ES🇪🇸 Palma de Mallorca → HR🇭🇷 Zagreb → IT🇮🇹 Milan
BGY -> PMI -> ZAG -> BGY
from 59.00 €
5h 25m total flight time
11-day trip
Milan BGY → Palma de Mallorca PMI 2026-10-20
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 → Zagreb ZAG 2026-10-22
from 22.00 € Ryanair 2h 25m prices last checked on 2026-07-14
Book a stay in Zagreb: Booking.com | Hostelworld
Zagreb ZAG → Milan BGY 2026-10-31
from 18.00 € Ryanair 1h 15m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → ES🇪🇸 Palma de Mallorca (2026-10-20) → HR🇭🇷 Zagreb (2026-10-22) → IT🇮🇹 Milan (2026-10-31)
Cheapest dates align
IT🇮🇹 Milan → IT🇮🇹 Palermo → SK🇸🇰 Bratislava → IT🇮🇹 Milan
MXP -> PMO -> BTS -> MXP
from 59.00 €
5h 40m total flight time
14-day trip
Milan MXP → Palermo PMO 2026-10-07
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 2026-10-16
from 25.00 € Ryanair 2h 15m prices last checked on 2026-07-14
Book a stay in Bratislava: Booking.com | Hostelworld
Bratislava BTS → Milan MXP 2026-10-21
from 19.00 € Ryanair 1h 35m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → IT🇮🇹 Palermo (2026-10-07) → SK🇸🇰 Bratislava (2026-10-16) → IT🇮🇹 Milan (2026-10-21)
Cheapest dates align
IT🇮🇹 Milan → FR🇫🇷 Paris → IE🇮🇪 Dublin → IT🇮🇹 Milan
BGY -> BVA -> DUB -> MXP
from 59.00 €
5h 45m total flight time
13-day trip
Milan BGY → Paris BVA 2026-10-01
from 20.00 € Ryanair 1h 35m prices last checked on 2026-07-14
Book a stay in Paris: Booking.com | Hostelworld
Paris BVA → Dublin DUB 2026-10-07
from 20.00 € Ryanair 1h 35m prices last checked on 2026-07-14
Book a stay in Dublin: Booking.com | Hostelworld
Dublin DUB → Milan MXP 2026-10-14
from 19.00 € Ryanair 2h 35m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → FR🇫🇷 Paris (2026-10-01) → IE🇮🇪 Dublin (2026-10-07) → IT🇮🇹 Milan (2026-10-14)
Cheapest dates align
IT🇮🇹 Milan → PL🇵🇱 Warsaw → SK🇸🇰 Bratislava → IT🇮🇹 Milan
MXP -> WAW -> BTS -> MXP
from 60.00 €
4h 45m total flight time
14-day trip
Milan MXP → Warsaw WAW 2026-10-07
from 20.00 € Wizz Air 1h 55m prices last checked on 2026-07-14
Book a stay in Warsaw: Booking.com | Hostelworld
Warsaw WAW → Bratislava BTS 2026-10-14
from 21.00 € Wizz Air 1h 15m prices last checked on 2026-07-14
Book a stay in Bratislava: Booking.com | Hostelworld
Bratislava BTS → Milan MXP 2026-10-21
from 19.00 € Ryanair 1h 35m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → PL🇵🇱 Warsaw (2026-10-07) → SK🇸🇰 Bratislava (2026-10-14) → IT🇮🇹 Milan (2026-10-21)
Cheapest dates align
IT🇮🇹 Milan → ES🇪🇸 Palma de Mallorca → HR🇭🇷 Zagreb → IT🇮🇹 Milan
MXP -> PMI -> ZAG -> BGY
from 60.00 €
5h 25m total flight time
12-day trip
Milan MXP → Palma de Mallorca PMI 2026-10-19
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 → Zagreb ZAG 2026-10-22
from 22.00 € Ryanair 2h 25m prices last checked on 2026-07-14
Book a stay in Zagreb: Booking.com | Hostelworld
Zagreb ZAG → Milan BGY 2026-10-31
from 18.00 € Ryanair 1h 15m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → ES🇪🇸 Palma de Mallorca (2026-10-19) → HR🇭🇷 Zagreb (2026-10-22) → IT🇮🇹 Milan (2026-10-31)
Cheapest dates align
IT🇮🇹 Milan → ES🇪🇸 Barcelona → AT🇦🇹 Vienna → IT🇮🇹 Milan
MXP -> BCN -> VIE -> BGY
from 60.00 €
5h 35m total flight time
16-day trip
Milan MXP → Barcelona BCN 2026-10-14
from 15.00 € Vueling 1h 45m prices last checked on 2026-07-14
Book a stay in Barcelona: Booking.com | Hostelworld
Barcelona BCN → Vienna VIE 2026-10-21
from 25.00 € Ryanair 2h 25m prices last checked on 2026-07-14
Book a stay in Vienna: Booking.com | Hostelworld
Vienna VIE → Milan BGY 2026-10-30
from 20.00 € Ryanair 1h 25m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → ES🇪🇸 Barcelona (2026-10-14) → AT🇦🇹 Vienna (2026-10-21) → IT🇮🇹 Milan (2026-10-30)
Cheapest dates align
IT🇮🇹 Milan → IT🇮🇹 Palermo → FR🇫🇷 Marseille → IT🇮🇹 Milan
MXP -> PMO -> MRS -> BGY
from 61.00 €
4h 45m total flight time
14-day trip
Milan MXP → Palermo PMO 2026-10-07
from 15.00 € Wizz Air 1h 50m prices last checked on 2026-07-14
Book a stay in Palermo: Booking.com | Hostelworld
Palermo PMO → Marseille MRS 2026-10-16
from 22.00 € Ryanair 1h 45m prices last checked on 2026-07-14
Book a stay in Marseille: Booking.com | Hostelworld
Marseille MRS → Milan BGY 2026-10-21
from 24.00 € Ryanair 1h 10m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → IT🇮🇹 Palermo (2026-10-07) → FR🇫🇷 Marseille (2026-10-16) → IT🇮🇹 Milan (2026-10-21)
Cheapest dates align
IT🇮🇹 Milan → ES🇪🇸 Barcelona → AT🇦🇹 Vienna → IT🇮🇹 Milan
MXP -> BCN -> VIE -> MXP
from 61.00 €
5h 40m total flight time
15-day trip
Milan MXP → Barcelona BCN 2026-10-14
from 15.00 € Vueling 1h 45m prices last checked on 2026-07-14
Book a stay in Barcelona: Booking.com | Hostelworld
Barcelona BCN → Vienna VIE 2026-10-21
from 25.00 € Ryanair 2h 25m prices last checked on 2026-07-14
Book a stay in Vienna: Booking.com | Hostelworld
Vienna VIE → Milan MXP 2026-10-29
from 21.00 € Ryanair 1h 30m prices last checked on 2026-07-14
Cheapest-date itinerary
IT🇮🇹 Milan → ES🇪🇸 Barcelona (2026-10-14) → AT🇦🇹 Vienna (2026-10-21) → IT🇮🇹 Milan (2026-10-29)
Prices marked "from X euros that month" are the cheapest fares observed that month; other dates may cost more.

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