$257 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 $257 One Way, $635 Round Trip from Chicago to Siena
Prices starting at $635 for return flights and $257 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
Aurum Firenze
Nov 6 - Nov 10
Chicago (CHI) to Florence (FLR)
Florence (FLR) to Chicago (CHI)
Reviewed on Sep 27, 2026
The Moon Boutique Hotel & Spa
Nov 6 - Nov 10
Chicago (CHI) to Florence (FLR)
Florence (FLR) to Chicago (CHI)
Reviewed on Sep 25, 2026
Hotel La Scaletta Al Ponte Vecchio
Nov 6 - Nov 10
Chicago (CHI) to Florence (FLR)
Florence (FLR) to Chicago (CHI)
Reviewed on Sep 26, 2026
Siena packages with premium economy flights
Dimora Palanca Boutique & SPA
Nov 7 - Nov 14
Chicago (ORD) to Florence (FLR)
Florence (FLR) to Chicago (ORD)
Reviewed on Sep 25, 2026
The James Suite Hotel Firenze 1564 - Small Luxury Hotels of the World
Nov 7 - Nov 14
Chicago (ORD) to Florence (FLR)
Florence (FLR) to Chicago (ORD)
Bernini Palace
Nov 7 - Nov 14
Chicago (ORD) to Florence (FLR)
Florence (FLR) to Chicago (ORD)
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
Trip-Planning Made Easy
Your search engine may give you thousands of pages of results when you search for cheap flights from Chicago to Siena, but you can save yourself a lot of hassle and money by going straight to Orbitz.com. Not only do we offer great deals on Chicago to Siena flights, but we make it easy to book hotels, car rentals, cruises, or a complete vacation package of your dreams.
Discount Chicago to Siena Flights
Orbitz’s low price guarantee means you get the best fares around. Find the lowest prices for international and domestic tickets and for flights from Chicago to Siena when you use Orbitz. It’s easy to add activities to your booking, so you can take advantage of all that Siena has to offer.
Easily Book, Change, Cancel Flights From Chicago to Siena
Orbitz now offers free mobile device apps, so even the busiest multi-taskers can plan their vacations while away from their desktop computer. Plus, instant alerts to your email or mobile phone help you stay on top of any delays or travel updates, so you avoid unpleasant surprises before boarding your Chicago to Siena flights. Our Customer Service representatives are ready to assist you if you need to change your air travel plans.
Take Advantage of Frequent Flyer Options Through Orbitz
With Orbitz, you do not have to choose between a low fare and earning frequent flyer miles. Simply provide your frequent flyer information when you book your Chicago to Siena flights.
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.