
Find Cheap Flights from Chicago (CHI) to Siena (FLR) from €708
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Selected flight deals from Chicago to Siena
The lowest prices found within the past 7 days from Chicago to Siena were €575 for one-way flights and €708 for return flights, for the period specified. Prices and availability are subject to change. Additional terms apply.
ORD
O'Hare Intl.
FLR
Peretola
€708 Return, found 5 hours ago
€708
Return
found 5 hours ago
ORD
O'Hare Intl.
FLR
Peretola
€729 Return, found 5 hours ago
€729
Return
found 5 hours ago
ORD
O'Hare Intl.
FLR
Peretola
€747 Return, found 5 hours ago
€747
Return
found 5 hours ago
ORD
O'Hare Intl.
FLR
Peretola
€753 Return, found 5 hours ago
€753
Return
found 5 hours ago
ORD
O'Hare Intl.
FLR
Peretola
€774 Return, found 5 hours ago
€774
Return
found 5 hours ago
Origin airport IATA code | ORD |
|---|---|
Destination airport IATA code | FLR |
Return price | €707 |
Best Day to Book Flight from Chicago to Siena
Siena Flight Information
Traveling From | Chicago |
|---|---|
Origin Airport IATA Code | CHI |
Traveling To | Siena |
Destination Airport IATA Code | FLR |
Number of Airlines Serving | |
Available Airlines | British Airways, Delta, Swiss International Air Lines, United, Lufthansa, Austrian Airlines |
Distance | |
Direct Flight Time | |
Flight Price | €708 |
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Place to stay after flight from Chicago to Siena

Hotel Chiusarelli
Viale Curtatone 15 Siena SI
Yövy tässä liikematkustukseen soveltuvassa hotellissa kohteessa Siena. Nauti ilmaisesta aamiaisesta, ilmaisesta Wi-Fi-yhteydestä ja huonepalvelusta. Asiakkaamme ...
8.8/10 Excellent! (1,002 reviews)
Clean and very friendly staff. Colazione was amazing
Reviewed on 18 Mar 2026

Palazzo Ravizza
Pian dei Mantellini 34 Siena SI
Yövy tässä hotellissa kohteessa Siena. Nauti ilmaisesta Wi-Fi-yhteydestä, huonepalvelusta ja pysäköinnistä (lisämaksusta). Asiakkaamme kehuvat majoituspaikan ...
9.4/10 Exceptional! (762 reviews)
Beautiful building. Clean and safe. Great breakfast buffet. Everything is in walking distance to hotel. One front desk staff member was not polite or welcoming but overall it was a lovely stay.
Reviewed on 17 Mar 2026

Hotel Executive
Via Nazareno Orlandi 32 Siena SI
Yövy tässä perheille sopivassa hotellissa kohteessa Siena. Nauti ilmaisesta Wi-Fi-yhteydestä, ilmaisesta pysäköinnistä ja aamiaisesta (lisämaksusta). Asiakkaamme ...
8.4/10 Very Good! (528 reviews)
The staff were super great .Took care of all our needs .Suggested the best winery tour .And the food was terrific .
Reviewed on 2 Nov 2025
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Hotel Italia
Viale Camillo Benso Conte di Cavour, 67 Siena SI
Yövy tässä hotellissa kohteessa Siena. Nauti ilmaisesta Wi-Fi-yhteydestä, aamiaisesta (lisämaksusta) ja huonepalvelusta. Asiakkaamme kehuvat majoituspaikan aamiaista ...
9.2/10 Wonderful! (1,000 reviews)
Very close to the bus and train station, lovely staff, clean room but a bit too warm even in February and no water kettle in the room, which was a bit surprising.
Reviewed on 8 Mar 2026

Four Points by Sheraton Siena
Via Antonio Lombardi 41 Siena SI
Yövy tässä liikematkustukseen soveltuvassa hotellissa kohteessa Siena. Nauti ilmaisesta aamiaisesta, ilmaisesta Wi-Fi-yhteydestä ja ilmaisesta pysäköinnistä. ...
8.8/10 Excellent! (584 reviews)
The air conditioning was bad. I was perspiring during my bed time. Other things were ok. Ample parking.
Reviewed on 30 Nov 2025

Villa Scacciapensieri Boutique Hotel
Strada di Scacciapensieri 10 Siena SI
Yövy tässä perheille sopivassa hotellissa kohteessa Siena. Nauti ilmaisesta aamiaisesta, ilmaisesta Wi-Fi-yhteydestä ja ulkouima-altaasta. Lähellä sijaitsevat ...
9.2/10 Wonderful! (422 reviews)
Stayed in this villa for a couple of nights. It’s a great option if you’re looking to escape the hustle and bustle of the city center. The location is lovely, with birds chirping in the background. The rooms were small, but they had all the necessary amenities for travelers. I had dinner and breakfast ...
Reviewed on 18 Mar 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Flight prices above are per person all prepaid taxes and online service fees included and subject to availability



