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€346–677Fly 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€284–657Fly 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 29m€401–836Fly 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 5m€333–695Fly to Venice Marco Polo Airport, train
- Fly from Chicago O'Hare International Airport (ORD) to Venice Marco Polo Airport (VCE)plane ORD - VCE
- Take the train from Venezia Mestre to Firenze S.M.N.train
- Take the train from Firenze S.M.N. to Sienatrain
19h 12m€396–857Fly 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€318–816
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 €280 - €700 and takes 17h.
The fastest way to get from Chicago to Siena is to fly and train which takes 16h 29m and costs €400 - €850.
The distance between Chicago and Siena is 7665 km.
It takes approximately 16h 36m to get from Chicago to Siena, including transfers.
Siena is 7h ahead of Chicago. It is currently 10:45 AM in Chicago and 5:45 PM in Siena.
There are 2409+ 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 27m
- When
- Every day
- Estimated price
- €260–1,300
Flights from Chicago O'Hare International Airport to Florence Peretola Airport via Munich
- Ave. Duration
- 11h 50m
- When
- Every day
- Estimated price
- €270–1,300
Flights from Chicago O'Hare International Airport to Pisa International Airport via Frankfurt
- Ave. Duration
- 11h 57m
- When
- Every day
- Estimated price
- €230–1,100
Flights from Chicago O'Hare International Airport to Bologna Guglielmo Marconi Airport via Frankfurt
- Ave. Duration
- 12h 56m
- When
- Every day
- Estimated price
- €220–1,100
Flights from Chicago O'Hare International Airport to Bologna Guglielmo Marconi Airport via Munich
- Ave. Duration
- 11h 52m
- When
- Every day
- Estimated price
- €220–1,100
Flights from Chicago O'Hare International Airport to Fiumicino International Airport
- Ave. Duration
- 9h 15m
- When
- Every day
- Estimated price
- €190–800
Flights from Chicago O'Hare International Airport to Fiumicino International Airport via Frankfurt
- Ave. Duration
- 12h 52m
- When
- Every day
- Estimated price
- €230–550
Flights from Chicago O'Hare International Airport to Venice Marco Polo Airport via Frankfurt
- Ave. Duration
- 11h 32m
- When
- Every day
- Estimated price
- €230–1,000
Flights from Chicago O'Hare International Airport to Venice Marco Polo Airport via Munich
- Ave. Duration
- 11h 52m
- 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
- €180–750
Flights from Chicago O'Hare International Airport to Milano Malpensa Airport via Munich
- Ave. Duration
- 11h 40m
- When
- Every day
- Estimated price
- €190–900
Flights from Chicago O'Hare International Airport to Milano Malpensa Airport via Frankfurt
- 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 Frankfurt
- Ave. Duration
- 12h 40m
- When
- Every day
- Estimated price
- €260–1,300
Flights from Chicago O'Hare International Airport to Florence Peretola Airport via Munich
- Ave. Duration
- 11h 50m
- When
- Every day
- Estimated price
- €270–1,300
Flights from Chicago O'Hare International Airport to Florence Peretola Airport via Zurich
- Ave. Duration
- 12h 5m
- When
- Every day
- Estimated price
- €260–1,100
Flights from Chicago O'Hare International Airport to Bologna Guglielmo Marconi Airport via Frankfurt
- Ave. Duration
- 12h 56m
- When
- Every day
- Estimated price
- €220–1,100
Flights from Chicago O'Hare International Airport to Bologna Guglielmo Marconi Airport via Munich
- Ave. Duration
- 11h 52m
- When
- Every day
- Estimated price
- €220–1,100
Flights from Chicago O'Hare International Airport to Bologna Guglielmo Marconi Airport via Brussels
- Ave. Duration
- 14h 25m
- When
- Monday, Tuesday, Wednesday, Thursday, Saturday, and Sunday
- Estimated price
- €220–900
Flights from Chicago O'Hare International Airport to Fiumicino International Airport
- Ave. Duration
- 9h 15m
- When
- Every day
- Estimated price
- €190–800
Flights from Chicago O'Hare International Airport to Fiumicino International Airport via Zurich
- Ave. Duration
- 12h 15m
- When
- Every day
- Estimated price
- €260–380
Flights from Chicago O'Hare International Airport to Fiumicino International Airport via Frankfurt
- Ave. Duration
- 12h 52m
- When
- Every day
- Estimated price
- €230–550
Flights from Chicago O'Hare International Airport to Venice Marco Polo Airport via Brussels
- Ave. Duration
- 10h 45m
- When
- Every day
- Estimated price
- €210–850
Flights from Chicago O'Hare International Airport to Venice Marco Polo Airport via Frankfurt
- Ave. Duration
- 11h 32m
- When
- Every day
- Estimated price
- €230–1,000
Flights from Chicago O'Hare International Airport to Venice Marco Polo Airport via Munich
- Ave. Duration
- 11h 52m
- When
- Every day
- Estimated price
- €210–1,000
Flights from Chicago O'Hare International Airport to Venice Marco Polo Airport via Zurich
- Ave. Duration
- 11h 55m
- When
- Every day
- Estimated price
- €210–900
Flights from Chicago O'Hare International Airport to Milano Malpensa Airport
- Ave. Duration
- 8h 50m
- When
- Every day
- Estimated price
- €180–750
Flights from Chicago O'Hare International Airport to Milano Malpensa Airport via Frankfurt
- Ave. Duration
- 12h
- When
- Every day
- Estimated price
- €200–850
Flights from Chicago O'Hare International Airport to Milano Malpensa Airport via Munich
- Ave. Duration
- 12h
- When
- Every day
- Estimated price
- €200–900
- Website
- swiss.com
Flights from Chicago O'Hare International Airport to Florence Peretola Airport via Zurich
- Ave. Duration
- 12h 22m
- When
- Every day
- Estimated price
- €260–1,100
Flights from Chicago O'Hare International Airport to Bologna Guglielmo Marconi Airport via Zurich
- Ave. Duration
- 11h 55m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- €210–900
Flights from Chicago O'Hare International Airport to Fiumicino International Airport
- Ave. Duration
- 9h 15m
- When
- Every day
- Estimated price
- €190–800
Flights from Chicago O'Hare International Airport to Fiumicino International Airport via Zurich
- Ave. Duration
- 11h 52m
- When
- Every day
- Estimated price
- €260–380
Flights from Chicago O'Hare International Airport to Venice Marco Polo Airport via Zurich
- Ave. Duration
- 12h 5m
- When
- Every day
- Estimated price
- €210–900
Flights from Chicago O'Hare International Airport to Milano Malpensa Airport
- Ave. Duration
- 8h 50m
- When
- Every day
- Estimated price
- €180–750
Flights from Chicago O'Hare International Airport to Milano Malpensa Airport via Zurich
- Ave. Duration
- 12h 7m
- When
- Every day
- Estimated price
- €180–750
- Website
- klm.com
Flights from Chicago O'Hare International Airport to Florence Peretola Airport via Paris Charles de Gaulle
- Ave. Duration
- 11h 10m
- When
- Every day
- Estimated price
- €260–1,100
Flights from Chicago O'Hare International Airport to Florence Peretola Airport via Amsterdam Schiphol
- Ave. Duration
- 11h 20m
- When
- Every day
- Estimated price
- €260–1,100
Flights from Chicago O'Hare International Airport to Pisa International Airport via Amsterdam Schiphol
- Ave. Duration
- 16h 10m
- When
- Thursday
- Estimated price
- €230–950
Flights from Chicago O'Hare International Airport to Bologna Guglielmo Marconi Airport via Amsterdam Schiphol
- Ave. Duration
- 12h 55m
- When
- Every day
- Estimated price
- €220–900
Flights from Chicago O'Hare International Airport to Fiumicino International Airport via Amsterdam Schiphol
- Ave. Duration
- 12h 25m
- When
- Every day
- Estimated price
- €200–800
Flights from Chicago O'Hare International Airport to Venice Marco Polo Airport via Amsterdam Schiphol
- Ave. Duration
- 11h 35m
- When
- Every day
- Estimated price
- €210–850
- Website
- austrian.com
Flights from Chicago O'Hare International Airport to Florence Peretola Airport via Vienna
- Ave. Duration
- 14h 45m
- When
- Monday, Tuesday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- €290–1,100
Flights from Chicago O'Hare International Airport to Bologna Guglielmo Marconi Airport via Vienna
- Ave. Duration
- 19h 5m
- When
- Monday, Tuesday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- €240–950
Flights from Chicago O'Hare International Airport to Fiumicino International Airport
- Ave. Duration
- 9h 15m
- When
- Every day
- Estimated price
- €190–800
Flights from Chicago O'Hare International Airport to Venice Marco Polo Airport via Vienna
- Ave. Duration
- 10h 55m
- When
- Monday, Tuesday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- €240–900
Flights from Chicago O'Hare International Airport to Milano Malpensa Airport
- Ave. Duration
- 8h 50m
- When
- Every day
- Estimated price
- €180–750
- Website
- airfrance.com
Flights from Chicago O'Hare International Airport to Florence Peretola Airport via Paris Charles de Gaulle
- Ave. Duration
- 11h 10m
- When
- Every day
- Estimated price
- €260–1,100
Flights from Chicago O'Hare International Airport to Bologna Guglielmo Marconi Airport via Paris Charles de Gaulle
- Ave. Duration
- 13h 50m
- When
- Monday, Tuesday, Wednesday, Friday, Saturday, and Sunday
- 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
- €190–800
Flights from Chicago O'Hare International Airport to Venice Marco Polo Airport via Paris Charles de Gaulle
- Ave. Duration
- 11h 40m
- When
- Every day
- Estimated price
- €210–850
- Website
- britishairways.com
Flights from Chicago O'Hare International Airport to Pisa International Airport via London Heathrow
- Ave. Duration
- 13h 8m
- When
- Every day
- Estimated price
- €230–900
Flights from Chicago O'Hare International Airport to Fiumicino International Airport
- Ave. Duration
- 9h 15m
- When
- Every day
- Estimated price
- €190–800
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Pisa International Airport via London Heathrow
- Ave. Duration
- 13h 8m
- When
- Every day
- Estimated price
- €230–900
Flights from Chicago O'Hare International Airport to Fiumicino International Airport
- Ave. Duration
- 9h 15m
- When
- Every day
- Estimated price
- €190–800
- Website
- brusselsairlines.com
Flights from Chicago O'Hare International Airport to Bologna Guglielmo Marconi Airport via Brussels
- Ave. Duration
- 14h 25m
- When
- Monday, Tuesday, Wednesday, Thursday, Saturday, and Sunday
- Estimated price
- €220–900
Flights from Chicago O'Hare International Airport to Fiumicino International Airport
- Ave. Duration
- 9h 15m
- When
- Every day
- Estimated price
- €190–800
Flights from Chicago O'Hare International Airport to Venice Marco Polo Airport via Brussels
- Ave. Duration
- 10h 45m
- When
- Every day
- Estimated price
- €210–850
Flights from Chicago O'Hare International Airport to Milano Malpensa Airport
- Ave. Duration
- 8h 50m
- When
- Every day
- Estimated price
- €180–750
- 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
- €380–600
Flights from Chicago O'Hare International Airport to Fiumicino International Airport
- Ave. Duration
- 9h 25m
- When
- Thursday and Saturday
- Estimated price
- €200–700
- Website
- aerlingus.com
Flights from Chicago O'Hare International Airport to Pisa International Airport via Dublin
- Ave. Duration
- 11h 5m
- When
- Tuesday, Thursday, and Saturday
- Estimated price
- €270–1,200
Flights from Chicago O'Hare International Airport to Venice Marco Polo Airport via Dublin
- Ave. Duration
- 12h 50m
- When
- Monday, Wednesday, Thursday, Friday, Saturday, and Sunday
- 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
- €12–21
- Website
- https://www.trenitalia.com/en.html
Train from Pisa Centrale to Empoli
- Ave. Duration
- 45 min
- Frequency
- Every 30 minutes
- Estimated price
- €6–11
- 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 51m
- Frequency
- Twice daily
- Estimated price
- €12–20
- Website
- https://www.trenitalia.com/en.html
Train from Roma Termini to Firenze S.M.N.
- Ave. Duration
- 3h 40m
- Frequency
- 5 times a day
- Estimated price
- €30–60
- 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
- €13–26
- 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 Venezia Mestre to Firenze S.M.N.
- Ave. Duration
- 2h 1m
- Frequency
- Hourly
- Estimated price
- €35–70
- Schedules at
- trenitalia.com
Train from Milano Centrale to Firenze S.M.N.
- Ave. Duration
- 1h 54m
- Frequency
- Hourly
- Estimated price
- €45–85
- 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 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
- €12–24
- Website
- https://www.italotreno.it/en
Train from Venezia Mestre to Firenze S.M.N.
- Ave. Duration
- 2h 11m
- Frequency
- Once a week
- Estimated price
- €30–65
- 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
- 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
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