Cheap Flights from Chicago to Florence
Cheap Flights from Chicago to Florence
Looking for cheap flights from Chicago to Florence? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Chicago to Florence vary by season, cabin, and date, but available award flights can start around 12,000–18,750 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Chicago to Florence for specific travel dates.
2026-11-27
ORD - FLR
Economy | 1 Stop | 9+ left
From 12,000 Pts + $180.6
2026-11-26
ORD - FLR
Economy | 1 Stop | 9+ left
From 12,000 Pts + $191.8
2026-12-04
ORD - FLR
Economy | 1 Stop | 6 left
From 18,750 Pts + $152.3
2026-12-05
ORD - FLR
Economy | 1 Stop | 9+ left
From 18,750 Pts + $152.3
2026-12-06
ORD - FLR
Economy | 1 Stop | 9+ left
From 18,750 Pts + $163.5
2026-12-07
ORD - FLR
Economy | 1 Stop | 9+ left
From 18,750 Pts + $163.5
Chicago to Florence flight facts
Distance
4,690 mi
7,548 km in a straight line
Estimated flight time
about 10h
In the air, for the straight-line distance
Time difference
+7h
Florence is 7 hours ahead of Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Florence
FLR · Peretola
Nearby airport alternatives
Flights Chicago - Bologna · Bologna is 50 mi from Florence
Flights Chicago - Venice · Venice is 130 mi from Florence
Flights Chicago - Rome · Rome is 148 mi from Florence
Flights Chicago - Milano · Milano is 161 mi from Florence
Premium cabin flights from Chicago to Florence
Premium cabin
2026-11-26
ORD - FLR
Business | 2 Stops
From 57,500 Pts + $757.3
Premium cabin
2026-11-25
ORD - FLR
Business | 1 Stop
From 57,500 Pts + $776.1
Premium cabin
2026-11-26
ORD - FLR
Business | 2 Stops | 6 left
From 75,000 Pts + $115
Premium cabin
2026-11-25
ORD - FLR
Business | 2 Stops | 1 left
From 85,000 Pts + $1593.3
Premium cabin
2026-11-26
ORD - FLR
Business | 2 Stops | 1 left
From 85,000 Pts + $1593.3
Premium cabin
2026-11-27
ORD - FLR
Business | 2 Stops | 2 left
From 85,000 Pts + $1593.3
Selected hotels for your next stay
Florence (Italy)
Villa Petriolo(SLH)
From 80,000 Pts or $246
Florence (Italy)
Hotel Regency(SLH)
From 105,000 Pts or $358
Castel Nuovo Dell Abate (Italy)
Mastrojanni Relais, an SLH Hotel
From 120,000 Pts or $444
Frequently Asked Questions
The cheapest route from Chicago to Florence depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Chicago to Florence.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Florence.
Chicago and Florence are about 4,690 miles (7,548 km) apart in a straight line.
Flying the 4,690-mile straight-line distance takes about 10h in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Florence is 7 hours ahead of Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Florence: Peretola (FLR).
Travelers searching this route also look at other popular routes into Florence, plus the return trip when we track it. Fares and award space change daily.
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