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.
Fly to Florence Peretola Airport, train
best- Fly from Chicago O'Hare International Airport (ORD) to Florence Peretola Airport (FLR)plane ORD - FLR
- Take the train from Firenze S.M.N. to Sienatrain
16h 36m€336–726Fly to Fiumicino International Airport, train
cheapest- Fly from Chicago O'Hare International Airport (ORD) to Fiumicino International Airport (FCO)plane ORD - FCO
- Take the train from Roma Termini to Firenze S.M.N.train
- Take the train from Firenze S.M.N. to Sienatrain
17h€294–656Fly to Pisa International Airport, train
- Fly from Chicago O'Hare International Airport (ORD) to Pisa International Airport (PSA)plane ORD - PSA
- Take the train from Pisa Centrale to Empolitrain
- Take the train from Empoli to Sienatrain
16h 4m€401–785Fly to Bologna Guglielmo Marconi Airport, train
- Fly from Chicago O'Hare International Airport (ORD) to Bologna Guglielmo Marconi Airport (BLQ)plane ORD - BLQ
- Take the train from Bologna Centrale to Firenze S.M.N.train
- Take the train from Firenze S.M.N. to Sienatrain
17h 30m€333–694Fly to Milan Linate Airport, train
- Fly from Chicago O'Hare International Airport (ORD) to Milan Linate Airport (LIN)plane ORD - LIN
- Take the train from Milano Rogoredo to Firenze S.M.N.train
- Take the train from Firenze S.M.N. to Sienatrain
18h 39m€345–799Fly to Milano Malpensa Airport, train
- Fly from Chicago O'Hare International Airport (ORD) to Milano Malpensa Airport (MXP)plane ORD - MXP
- Take the train from Malpensa Aeroporto T1 to Milano Centraletrain
- Take the train from Milano Centrale to Firenze S.M.N.train
- Take the train from Firenze S.M.N. to Sienatrain
17h 54m€328–865
Chicago O'Hare International Airport (ORD) to Florence Peretola Airport (FLR) flights
Questions & Answers
The cheapest way to get from Chicago to Siena is to fly and train which costs €290 - €700 and takes 17h.
The fastest way to get from Chicago to Siena is to fly and train which takes 16h 4m and costs €400 - €800.
The distance between Chicago and Siena is 7665 km.
It takes approximately 16h 36m to get from Chicago to Siena, including transfers.
Siena is 6h ahead of Chicago. It is currently 8:41 AM in Chicago and 2:41 PM in Siena.
There are 2369+ hotels available in Siena.
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 Train Station, take the train to Pisa Centrale, take the train to Empoli, then take the train to Siena.
- Website
- lufthansa.com
Flights from Chicago O'Hare International Airport to Florence Peretola Airport via Frankfurt
- Ave. Duration
- 12h 3m
- When
- Every day
- Estimated price
- €250–1,200
Flights from Chicago O'Hare International Airport to Florence Peretola Airport via Munich
- Ave. Duration
- 11h 45m
- When
- Every day
- Estimated price
- €260–1,200
Flights from Chicago O'Hare International Airport to Pisa International Airport via Frankfurt
- Ave. Duration
- 11h 30m
- When
- Friday and Saturday
- Estimated price
- €250–1,100
Flights from Chicago O'Hare International Airport to Bologna Guglielmo Marconi Airport via Frankfurt
- Ave. Duration
- 12h 47m
- When
- Every day
- Estimated price
- €210–1,000
Flights from Chicago O'Hare International Airport to Bologna Guglielmo Marconi Airport via Munich
- Ave. Duration
- 11h 47m
- When
- Every day
- Estimated price
- €210–1,000
Flights from Chicago O'Hare International Airport to Fiumicino International Airport
- Ave. Duration
- 9h 15m
- When
- Every day
- Estimated price
- €190–750
Flights from Chicago O'Hare International Airport to Fiumicino International Airport via Frankfurt
- Ave. Duration
- 12h 47m
- When
- Every day
- Estimated price
- €230–550
Flights from Chicago O'Hare International Airport to Fiumicino International Airport via Munich
- Ave. Duration
- 13h 35m
- When
- Every day
- Estimated price
- €230–550
Flights from Chicago O'Hare International Airport to Milan Linate Airport via Frankfurt
- Ave. Duration
- 12h 27m
- When
- Monday to Saturday
- Estimated price
- €230–1,000
Flights from Chicago O'Hare International Airport to Milan Linate Airport via Munich
- Ave. Duration
- 12h 35m
- When
- Every day
- Estimated price
- €210–1,000
Flights from Chicago O'Hare International Airport to Milano Malpensa Airport
- Ave. Duration
- 8h 50m
- When
- Every day
- Estimated price
- €170–700
Flights from Chicago O'Hare International Airport to Milano Malpensa Airport via Frankfurt
- Ave. Duration
- 12h
- When
- Every day
- Estimated price
- €190–850
Flights from Chicago O'Hare International Airport to Milano Malpensa Airport via Munich
- Ave. Duration
- 12h
- When
- Every day
- Estimated price
- €200–850
- Website
- united.com
Flights from Chicago O'Hare International Airport to Florence Peretola Airport via Brussels
- Ave. Duration
- 11h 5m
- When
- Tuesday, Wednesday, Friday, Saturday, and Sunday
- Estimated price
- €250–1,000
Flights from Chicago O'Hare International Airport to Florence Peretola Airport via Frankfurt
- Ave. Duration
- 11h 35m
- When
- Monday, Wednesday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- €250–1,100
Flights from Chicago O'Hare International Airport to Florence Peretola Airport via Zurich
- Ave. Duration
- 11h 40m
- When
- Every day
- Estimated price
- €260–1,000
Flights from Chicago O'Hare International Airport to Florence Peretola Airport via Munich
- Ave. Duration
- 11h 45m
- When
- Every day
- Estimated price
- €260–1,200
Flights from Chicago O'Hare International Airport to Bologna Guglielmo Marconi Airport via Frankfurt
- Ave. Duration
- 12h 51m
- When
- Tuesday to Sunday
- Estimated price
- €210–1,000
Flights from Chicago O'Hare International Airport to Bologna Guglielmo Marconi Airport via Munich
- Ave. Duration
- 11h 47m
- When
- Every day
- Estimated price
- €210–1,000
Flights from Chicago O'Hare International Airport to Bologna Guglielmo Marconi Airport via Brussels
- Ave. Duration
- 15h 25m
- When
- Monday, Tuesday, Thursday, Saturday, and Sunday
- Estimated price
- €210–850
Flights from Chicago O'Hare International Airport to Fiumicino International Airport
- Ave. Duration
- 9h 15m
- When
- Every day
- Estimated price
- €190–750
Flights from Chicago O'Hare International Airport to Fiumicino International Airport via Zurich
- Ave. Duration
- 11h 55m
- When
- Every day
- Estimated price
- €260–390
Flights from Chicago O'Hare International Airport to Fiumicino International Airport via Frankfurt
- Ave. Duration
- 12h 47m
- When
- Every day
- Estimated price
- €230–550
Flights from Chicago O'Hare International Airport to Fiumicino International Airport via Munich
- Ave. Duration
- 13h 35m
- When
- Every day
- Estimated price
- €230–550
Flights from Chicago O'Hare International Airport to Milan Linate Airport via Brussels
- Ave. Duration
- 10h 55m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- €200–850
Flights from Chicago O'Hare International Airport to Milan Linate Airport via Frankfurt
- Ave. Duration
- 12h 27m
- When
- Monday to Saturday
- Estimated price
- €230–1,000
Flights from Chicago O'Hare International Airport to Milano Malpensa Airport
- Ave. Duration
- 8h 50m
- When
- Every day
- Estimated price
- €170–700
Flights from Chicago O'Hare International Airport to Milano Malpensa Airport via Frankfurt
- Ave. Duration
- 12h
- When
- Every day
- Estimated price
- €190–850
Flights from Chicago O'Hare International Airport to Milano Malpensa Airport via Munich
- Ave. Duration
- 12h
- When
- Every day
- Estimated price
- €200–850
- Website
- swiss.com
Flights from Chicago O'Hare International Airport to Florence Peretola Airport via Zurich
- Ave. Duration
- 11h 25m
- When
- Every day
- Estimated price
- €260–1,000
Flights from Chicago O'Hare International Airport to Bologna Guglielmo Marconi Airport via Zurich
- Ave. Duration
- 11h 45m
- When
- Monday, Tuesday, Wednesday, Thursday, and Sunday
- Estimated price
- €210–850
Flights from Chicago O'Hare International Airport to Fiumicino International Airport
- Ave. Duration
- 9h 15m
- When
- Every day
- Estimated price
- €190–750
Flights from Chicago O'Hare International Airport to Fiumicino International Airport via Zurich
- Ave. Duration
- 11h 37m
- When
- Every day
- Estimated price
- €260–390
Flights from Chicago O'Hare International Airport to Milano Malpensa Airport
- Ave. Duration
- 8h 50m
- When
- Every day
- Estimated price
- €170–700
Flights from Chicago O'Hare International Airport to Milano Malpensa Airport via Zurich
- Ave. Duration
- 12h
- When
- Every day
- Estimated price
- €180–700
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Pisa International Airport via London Heathrow
- Ave. Duration
- 12h 11m
- When
- Saturday
- Estimated price
- €220–900
Flights from Chicago O'Hare International Airport to Fiumicino International Airport
- Ave. Duration
- 9h 15m
- When
- Every day
- Estimated price
- €190–750
Flights from Chicago O'Hare International Airport to Milan Linate Airport via London Heathrow
- Ave. Duration
- 11h 21m
- When
- Monday, Tuesday, Wednesday, Thursday, and Sunday
- Estimated price
- €200–800
Flights from Chicago O'Hare International Airport to Milan Linate Airport via Dublin
- Ave. Duration
- 11h 55m
- When
- Every day
- Estimated price
- €250–1,100
- Website
- britishairways.com
Flights from Chicago O'Hare International Airport to Pisa International Airport via London Heathrow
- Ave. Duration
- 12h 11m
- When
- Saturday
- Estimated price
- €220–900
Flights from Chicago O'Hare International Airport to Fiumicino International Airport
- Ave. Duration
- 9h 15m
- When
- Every day
- Estimated price
- €190–750
Flights from Chicago O'Hare International Airport to Milan Linate Airport via London Heathrow
- Ave. Duration
- 11h 21m
- When
- Monday, Tuesday, Wednesday, Thursday, and Sunday
- Estimated price
- €200–800
- Website
- brusselsairlines.com
Flights from Chicago O'Hare International Airport to Florence Peretola Airport via Brussels
- Ave. Duration
- 11h 5m
- When
- Tuesday, Wednesday, Friday, Saturday, and Sunday
- Estimated price
- €250–1,000
Flights from Chicago O'Hare International Airport to Bologna Guglielmo Marconi Airport via Brussels
- Ave. Duration
- 15h 25m
- When
- Monday, Tuesday, Thursday, Saturday, and Sunday
- Estimated price
- €210–850
Flights from Chicago O'Hare International Airport to Fiumicino International Airport
- Ave. Duration
- 9h 15m
- When
- Every day
- Estimated price
- €190–750
Flights from Chicago O'Hare International Airport to Milan Linate Airport via Brussels
- Ave. Duration
- 10h 55m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- €200–850
Flights from Chicago O'Hare International Airport to Milano Malpensa Airport
- Ave. Duration
- 8h 50m
- When
- Every day
- Estimated price
- €170–700
- Website
- klm.com
Flights from Chicago O'Hare International Airport to Florence Peretola Airport via Amsterdam Schiphol
- Ave. Duration
- 11h 5m
- When
- Every day
- Estimated price
- €250–1,000
Flights from Chicago O'Hare International Airport to Florence Peretola Airport via Paris Charles de Gaulle
- Ave. Duration
- 11h 15m
- When
- Every day
- Estimated price
- €250–1,000
Flights from Chicago O'Hare International Airport to Bologna Guglielmo Marconi Airport via Amsterdam Schiphol
- Ave. Duration
- 13h
- When
- Every day
- Estimated price
- €210–850
Flights from Chicago O'Hare International Airport to Fiumicino International Airport via Amsterdam Schiphol
- Ave. Duration
- 12h 25m
- When
- Every day
- Estimated price
- €190–800
Flights from Chicago O'Hare International Airport to Milan Linate Airport via Amsterdam Schiphol
- Ave. Duration
- 10h 40m
- When
- Every day
- Estimated price
- €200–850
- Website
- airfrance.com
Flights from Chicago O'Hare International Airport to Florence Peretola Airport via Paris Charles de Gaulle
- Ave. Duration
- 11h 15m
- When
- Every day
- Estimated price
- €250–1,000
Flights from Chicago O'Hare International Airport to Bologna Guglielmo Marconi Airport via Paris Charles de Gaulle
- Ave. Duration
- 13h 50m
- When
- Saturday
- Estimated price
- €210–850
Flights from Chicago O'Hare International Airport to Fiumicino International Airport via Paris Charles de Gaulle
- Ave. Duration
- 11h 15m
- When
- Every day
- Estimated price
- €190–750
Flights from Chicago O'Hare International Airport to Milan Linate Airport via Paris Charles de Gaulle
- Ave. Duration
- 11h 5m
- When
- Every day
- Estimated price
- €200–850
Flights from Chicago O'Hare International Airport to Milano Malpensa Airport via Paris Charles de Gaulle
- Ave. Duration
- 11h 30m
- When
- Monday, Tuesday, Wednesday, Thursday, and Sunday
- Estimated price
- €170–700
- Website
- austrian.com
Flights from Chicago O'Hare International Airport to Florence Peretola Airport via Vienna
- Ave. Duration
- 14h 45m
- When
- Monday, Tuesday, Thursday, Saturday, and Sunday
- Estimated price
- €300–1,100
Flights from Chicago O'Hare International Airport to Bologna Guglielmo Marconi Airport via Vienna
- Ave. Duration
- 19h 5m
- When
- Every day
- Estimated price
- €240–900
Flights from Chicago O'Hare International Airport to Fiumicino International Airport
- Ave. Duration
- 9h 15m
- When
- Every day
- Estimated price
- €190–750
Flights from Chicago O'Hare International Airport to Milan Linate Airport via Vienna
- Ave. Duration
- 14h 50m
- When
- Every day
- Estimated price
- €250–900
Flights from Chicago O'Hare International Airport to Milano Malpensa Airport
- Ave. Duration
- 8h 50m
- When
- Every day
- Estimated price
- €170–700
- Website
- ita-airways.com
Flights from Chicago O'Hare International Airport to Florence Peretola Airport via Fiumicino International Airport
- Ave. Duration
- 12h 40m
- When
- Thursday and Saturday
- Estimated price
- €290–950
Flights from Chicago O'Hare International Airport to Fiumicino International Airport
- Ave. Duration
- 9h 25m
- When
- Thursday and Saturday
- Estimated price
- €200–700
- Website
- ryanair.com
Flights from Chicago O'Hare International Airport to Pisa International Airport via Dublin
- Ave. Duration
- 11h
- When
- Tuesday, Friday, and Saturday
- Estimated price
- €260–1,200
Flights from Chicago O'Hare International Airport to Pisa International Airport via Madrid
- Ave. Duration
- 11h 46m
- When
- Thursday and Friday
- Estimated price
- €230–950
- Website
- aerlingus.com
Flights from Chicago O'Hare International Airport to Milan Linate Airport via Dublin
- Ave. Duration
- 11h 55m
- When
- Every day
- Estimated price
- €250–1,100
- Phone
- +39.06.5210550
- Website
- trenitalia.com
Train from Firenze S.M.N. to Siena
- Ave. Duration
- 1h 30m
- Frequency
- Hourly
- Estimated price
- €12–20
- Website
- https://www.trenitalia.com/en.html
Train from Pisa Centrale to Empoli
- Ave. Duration
- 45 min
- Frequency
- Every 30 minutes
- Estimated price
- €6–10
- Website
- https://www.trenitalia.com/en.html
Train from Empoli to Siena
- Ave. Duration
- 1h
- Frequency
- Hourly
- Estimated price
- €8–14
- Website
- https://www.trenitalia.com/en.html
Train from Bologna Centrale to Firenze S.M.N.
- Ave. Duration
- 1h 35m
- Frequency
- Twice daily
- Estimated price
- €11–20
- Website
- https://www.trenitalia.com/en.html
Train from Roma Termini to Firenze S.M.N.
- Ave. Duration
- 4h 22m
- Frequency
- 5 times a day
- Estimated price
- €30–55
- Website
- https://www.trenitalia.com/en.html
- Phone
- +39 06 68475475
- Website
- trenitalia.com
Train from Bologna Centrale to Firenze S.M.N.
- Ave. Duration
- 37 min
- Frequency
- Every 30 minutes
- Estimated price
- €13–25
- Schedules at
- trenitalia.com
Train from Roma Termini to Firenze S.M.N.
- Ave. Duration
- 1h 37m
- Frequency
- Every 30 minutes
- Estimated price
- €35–75
- Schedules at
- trenitalia.com
Train from Milano Rogoredo to Firenze S.M.N.
- Ave. Duration
- 1h 44m
- Frequency
- Hourly
- Estimated price
- €40–80
- Schedules at
- trenitalia.com
Train from Milano Centrale to Firenze S.M.N.
- Ave. Duration
- 1h 54m
- Frequency
- Hourly
- Estimated price
- €40–85
- Schedules at
- trenitalia.com
- Phone
- +39 06 68475475
- Website
- trenitalia.com
Train from Bologna Centrale to Firenze S.M.N.
- Ave. Duration
- 1h 16m
- Frequency
- Once daily
- Estimated price
- €9–21
- Website
- https://www.trenitalia.com/en.html
Train from Roma Termini to Firenze S.M.N.
- Ave. Duration
- 3h 45m
- Frequency
- 6 times a week
- Estimated price
- €26–60
- Website
- https://www.trenitalia.com/en.html
Train from Milano Rogoredo to Firenze S.M.N.
- Ave. Duration
- 3h 22m
- Frequency
- Once daily
- Estimated price
- €29–70
- Website
- https://www.trenitalia.com/en.html
Train from Milano Centrale to Firenze S.M.N.
- Ave. Duration
- 3h 42m
- Frequency
- Once daily
- Estimated price
- €30–70
- Website
- https://www.trenitalia.com/en.html
- Phone
- +39 06 8937 1892
- Website
- italotreno.it
Train from Bologna Centrale to Firenze S.M.N.
- Ave. Duration
- 46 min
- Frequency
- Once a week
- Estimated price
- €11–23
- Website
- https://www.italotreno.it/en
- Phone
- +39 06 68475475
- ufficiogruppi@trenitalia.it
- Website
- trenitalia.com
Train from Bologna Centrale to Firenze S.M.N.
- Ave. Duration
- 59 min
- Frequency
- Once a week
- Estimated price
- €27–70
- Website
- https://www.trenitalia.com/en.html
- 1st Class
- €45–70
- 2nd Class
- €27–40
Train from Milano Rogoredo to Firenze S.M.N.
- Ave. Duration
- 3h 18m
- Frequency
- Once a week
- Estimated price
- €65–120
- Website
- https://www.trenitalia.com/en.html
- 1st Class
- €80–120
- 2nd Class
- €65–90
- Phone
- +39 02 7249 4494
- my-link@trenord.it
- Website
- trenord.it
Train from Malpensa Aeroporto T1 to Milano Centrale
- Ave. Duration
- 56 min
- Frequency
- Every 30 minutes
- Estimated price
- €4–6
- Website
- https://www.trenord.it/en/
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 guide
5 incredible day trips from Florence by train
Read the travel guide
Getting to Rome from the airport
Read the travel guide




























