Rome2Rio

How to get fromChicago to Sienaby plane or train

Find Transport to Siena

See all options

There are 6 ways to get from Chicago to Siena by plane or train

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 Florence Peretola Airport, train

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Florence Peretola Airport (FLR)plane plane ORD - FLR
    2. Take the train from Firenze S.M.N. to Sienatrain train
    16h 31m
    €365–1,017

  2. Fly to Bologna Guglielmo Marconi Airport, train

    cheapest
    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 Florence Santa Maria Novellatrain train
    3. Take the train from Firenze S.M.N. to Sienatrain train
    17h 33m
    €264–769

  3. Fly to Pisa International Airport, train

    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 8m
    €342–774

  4. Fly to Fiumicino International Airport, train

    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 Florence Santa Maria Novellatrain train
    3. Take the train from Firenze S.M.N. to Sienatrain train
    16h 47m
    €273–783

  5. Fly to Milan Linate Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Milan Linate Airport (LIN)plane plane ORD - LIN
    2. Take the train from Milano Rogoredo to Firenze S.M.N.train train
    3. Take the train from Firenze S.M.N. to Sienatrain train
    18h 37m
    €330–890

  6. Fly to Milano Malpensa Airport, train

    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 train from Firenze S.M.N. to Sienatrain train
    17h 45m
    €290–856

Chicago O'Hare International Airport (ORD) to Florence Peretola Airport (FLR) flights

Calendar40Weekly Planes
Duration11h 51mAverage Duration
Ticket€246Cheapest Price
See schedules

Questions & Answers

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 Florence Peretola Airport (FLR), walk to Florence Airport (FLR), take the vehicle to Alamanni - Stazione Smn, walk to Firenze S.M.N., 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 Pisa International Airport (PSA), walk to Pisa Airport, take the train to Pisa Centrale, take the train to Empoli, then take the train to Siena.

Airlines
Train operators

Want to know more about travelling around Italy

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Italy Travel Guides

Read the travel guideItaly Travel Guides

Where to next?

Trips from Chicago

Trips to Siena

Popular routes