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How to get fromChicago to Sienaby plane, train, or bus

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There are 8 ways to get from Chicago to Siena by plane, train, or bus

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly to Pisa International Airport, train

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Pisa International Airport (PSA)plane plane ORD - PSA
    2. Take the train from Pisa Centrale to Empolitrain train
    3. Take the train from Empoli to Sienatrain train
    16h 23m
    €519–884

  2. Fly to Venice Marco Polo Airport, train, bus

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Venice Marco Polo Airport (VCE)plane plane ORD - VCE
    2. Take the train from Venezia Mestre to Firenze S.M.N.train train
    3. Take the bus from Firenze Autostazione to Siena-V Le V.Veneto N.5bus bus
    18h 18m
    €338–847

  3. Fly to Florence Peretola Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Florence Peretola Airport (FLR)plane plane ORD - FLR
    2. Take the train from Firenze Rifredi to Sienatrain train
    16h 4m
    €374–875

  4. Fly to Bologna Guglielmo Marconi Airport, train, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Bologna Guglielmo Marconi Airport (BLQ)plane plane ORD - BLQ
    2. Take the train from Bologna Centrale to Firenze S.M.N.train train
    3. Take the bus from Firenze Autostazione to Siena-V Le V.Veneto N.5bus bus
    16h 5m
    €375–780

  5. Fly to Fiumicino International Airport, train, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Fiumicino International Airport (FCO)plane plane ORD - FCO
    2. Take the train from Roma Termini to Firenze S.M.N.train train
    3. Take the bus from Firenze Autostazione to Siena-V Le V.Veneto N.5bus bus
    16h 6m
    €376–1,192

  6. Fly to Milano Malpensa Airport, train, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Milano Malpensa Airport (MXP)plane plane ORD - MXP
    2. Take the train from Malpensa Aeroporto T1 to Milano Centraletrain train
    3. Take the train from Milano Centrale to Firenze S.M.N.train train
    4. Take the bus from Firenze Autostazione to Siena-V Le V.Veneto N.5bus bus
    16h 44m
    €380–856

  7. Fly to Naples Airport, train, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Naples Airport (NAP)plane plane ORD - NAP
    2. Take the train from Napoli Centrale to Firenze S.M.N.train train
    3. Take the bus from Firenze Autostazione to Siena-V Le V.Veneto N.5bus bus
    17h 45m
    €451–1,105

  8. Fly to Raffaello Sanzio Airport, train, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Raffaello Sanzio Airport (AOI)plane plane ORD - AOI
    2. Take the train from Ancona to Bologna Centraletrain train
    3. Take the train from Bologna Centrale to Firenze S.M.N.train train
    4. Take the bus from Firenze Autostazione to Siena-V Le V.Veneto N.5bus bus
    20h 25m
    €457–1,549

Chicago O'Hare International Airport (ORD) to Pisa International Airport (PSA) flights

Calendar31Weekly Planes
Duration12h 38mAverage Duration
Ticket€305Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Siena.ExpandLaunch map view
  • Distance: 7,634 km
  • Duration: 16h 23m

What companies run services between Chicago, IL, USA and Siena, Italy?

There is no direct connection from Chicago to Siena. However, you can take the subway to O'Hare, walk to Chicago O'Hare International Airport (ORD) airport, fly to Pisa International Airport (PSA), walk to Pisa Airport Train Station, take the train to Pisa Centrale, take the train to Empoli, then take the train to Siena. Alternatively, you can take the subway to O'Hare, walk to Chicago O'Hare International Airport (ORD) airport, fly to Florence Peretola Airport (FLR), walk to Firenze T2 Guidoni, take the line 23 bus to Campo Sportivo Rifredi, walk to Firenze Rifredi, then take the train to Siena.

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