$292 Cheap flight deals from Chicago (CHI) to Siena (FLR)
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
This Weekend's Flight Deals from Chicago to Siena
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $292 One Way, $635 Round Trip from Chicago to Siena
Prices starting at $635 for return flights and $292 for one-way flights to Siena were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Siena economy flight packages
The Moon Boutique Hotel & Spa
Nov 16 - Nov 21
Chicago (CHI) to Florence (FLR)
Reviewed on Sep 28, 2026
Hotel La Scaletta Al Ponte Vecchio
Nov 16 - Nov 21
Chicago (CHI) to Florence (FLR)
Reviewed on Sep 26, 2026
Bernini Palace
Nov 16 - Nov 21
Chicago (CHI) to Florence (FLR)
Reviewed on Sep 29, 2026
More About Flying To Siena from Chicago
Route Information for Flights from Chicago to Siena
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | FLR |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Siena
Low Cost Flights From Chicago to Siena
Tired of the endless online search for the cheapest flights from Chicago to Siena? Save the energy for your vacation by using Orbitz to plan your next air trip. Orbitz guarantees the lowest prices on Chicago to Siena flights, and our cutting-edge mobile tools mean you can search and book flights with your iPhone, Android phone, iPad, or tablet.
Book Discount Chicago to Siena Flights With Ease
Take advantage of amazing sales on international and domestic fares, including bargain flights from Chicago to Siena. Not only do you find cheap deals on Orbitz, we make researching and planning your trip online and booking your tickets a breeze. Our discount Chicago to Siena flights keep more money in your pocket for your travel adventures.
Plan Flights From Chicago to Siena Anywhere, Anytime
Planning your vacation has never been easier using the convenient Orbitz apps available for most mobile devices. If there are any changes or delays for Chicago to Siena flights, Orbitz customers receive instant free alerts via email or mobile phone text message. Change or cancel flights from Chicago to Siena anytime online or by calling our Customer Service representatives.
Frequent Flyer? Earn Miles and Points Through Orbitz!
Earn points or miles on your low fare Chicago to Siena flights with Orbitz, just as you would by booking directly with the airline. Be sure to include your frequent flyer details when you book qualifying flights from Chicago to Siena on the Orbitz website.
Flights from Chicago
- Chicago to Houston
- Chicago to Orlando
- Chicago to New York
- Chicago to Phoenix
- Chicago to Dallas
- Chicago to Los Angeles
- Chicago to New Orleans
- Chicago to Washington
- Chicago to London
- Chicago to Paris
- Chicago to Rome
- Chicago to Toronto
- Chicago to San Francisco
- Chicago to Cleveland
- Chicago to Detroit
- Chicago to Sacramento
- Chicago to Montreal
- Chicago to Kansas City
- Chicago to Atlantic City
- Chicago to Hartford
More Destinations
- Province of Siena Hotels
- Castles in Province of Siena
- Villas in Province of Siena
- Sovicille Hotels
- Castelnuovo Berardenga Hotels
- Villas in Castelnuovo Berardenga
- 4 Star Hotels in Castellina in Chianti
- Castellina in Chianti Hotels
- Villas in Castellina in Chianti
- Gaiole in Chianti Hotels
- Siena City Centre Hotels
- San Sano Hotels
- Lucignano d'Arbia Hotels
- Sensano Hotels
- Farmstay in Ville di Corsano
- Ville di Corsano Hotels
- B&B in Orgia
- Castles in Pievescola
- Pievescola Hotels
- Casciano di Murlo Hotels
- Hotels near Monteriggioni Castle
- Resorts in Cavallari
- Hotels near Piazza del Campo
- Ponte A Bozzone Hotels
- Lecchi in Chianti Hotels
- Villas in Stigliano
- Colle Petroso Hotels
- Monteriggioni Hotels
- Castles in Cignan Bianco
- Castellina Scalo Hotels
- Vacation Homes in Castellina Scalo
- Siena Historical Center Hotels
- Hotels near Meleto Castle
- Villa A Sesta Hotels
- Colle Malamerenda Hotels
- Flights to Province of Siena
- Flights from Beijing to Empolese Val d'Elsa
- Flights from Chicago to Empolese Val d'Elsa
- Flights from Phoenix to Empolese Val d'Elsa
- Flights from Casablanca to Empolese Val d'Elsa
- Flights from Montechiaro
- Flights from Castellina in Chianti
- Flights from Copenhagen to Montepulciano
- Flights from New York to Montepulciano
- Flights from San Francisco to Montepulciano
- Flights from Toronto to Montepulciano
- Flights from Oakland to Montepulciano
- Flights from Birmingham to Montepulciano
- Flights from Buffalo to Montepulciano
- Flights from Charlotte to Chianti Region
- Flights from Chicago to Chianti Region
- Flights from Detroit to Chianti Region
- Flights from Minneapolis - St. Paul to Chianti Region
- Flights from Philadelphia to Chianti Region
- Flights from Vico D'arbia
- Flights from lsola d'Arbia
- Flights from Izmir to Florence
- Flights from Cincinnati to Florence
- Flights from Mexico City to Florence
- Flights from Tokyo to Florence
- Flights from Prague to Florence
- Flights from Québec City to Florence
- Flights from Muscat to Florence
- Flights from Minot to Florence
- Flights from Carpiquet to Florence
- Flights from Alghero to Florence
- Flights from Nespouls to Florence
- Flights from Richmond to Florence
- Flights from Newburgh to Florence
- Flights from Milwaukee to Florence
- Flights from Shreveport to Florence
- Flights from Oklahoma City to Florence
- Flights from Fort Wayne to Florence
- Flights from Porto to Florence
- Flights from Binghamton to Florence
- Flights from Savannah to Florence
- Flights from San Luis Obispo to Florence
- Flights from Kalispell to Florence
- Flights from Edinburgh to Florence
- Flights from Sudbury to Florence
- Flights from Sidney to Florence
- Flights from Chicago to Val d'Elsa
- Flights from Los Angeles to Val d'Elsa
- Flights from Minneapolis - St. Paul to Val d'Elsa
- Flights from Orlando to Val d'Elsa
- Flights from San Francisco to Val d'Elsa
- Flights from San Felice
- Flights from Columbus to Volterra
- Flights from Indianapolis to Volterra
- Flights from Las Vegas to Volterra
- Flights from Manila to Volterra
- Flights from Miami to Volterra
- Flights from Phoenix to Volterra
- Flights from San Francisco to Volterra
- Flights from Vancouver to Volterra
- Flights from Boise to Volterra
Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.