Cheap Flights from Chicago to Tallahassee
Cheap Flights from Chicago to Tallahassee
Looking for cheap flights from Chicago to Tallahassee? 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 Tallahassee vary by season, cabin, and date, but available award flights can start around 7,500–15,000 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 Tallahassee for specific travel dates.
2026-11-09
ORD - TLH
Economy | 1 Stop | 9+ left
From 7,500 Pts + $31.2
2026-11-05
ORD - TLH
Economy | 1 Stop
From 15,000 Pts + $5.6
2026-11-05
ORD - TLH
Economy | 1 Stop
From 15,000 Pts + $5.6
2026-11-06
ORD - TLH
Economy | 1 Stop
From 15,000 Pts + $5.6
2026-11-06
ORD - TLH
Economy | 1 Stop
From 15,000 Pts + $5.6
2026-11-07
ORD - TLH
Economy | 1 Stop
From 15,000 Pts + $5.6
Chicago to Tallahassee flight facts
Distance
819 mi
1,318 km in a straight line
Estimated flight time
about 2h 15m
In the air, for the straight-line distance
Time difference
+1h
Tallahassee is 1 hour ahead of Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Tallahassee
TLH · Tallahassee Regional
Nearby airport alternatives
Flights Chicago - Panama City · Panama City is 86 mi from Tallahassee
Flights Chicago - Valparaiso · Valparaiso is 130 mi from Tallahassee
Flights Chicago - Jacksonville · Jacksonville is 159 mi from Tallahassee
Flights Chicago - Pensacola · Pensacola is 169 mi from Tallahassee
Premium cabin flights from Chicago to Tallahassee
Premium cabin
2026-11-09
ORD - TLH
First | 1 Stop | 3 left
From 25,500 Pts + $11.2
Premium cabin
2026-11-05
ORD - TLH
First | 2 Stops | 2 left
From 25,500 Pts + $5.6
Premium cabin
2026-11-05
ORD - TLH
First | 2 Stops | 2 left
From 25,500 Pts + $5.6
Premium cabin
2026-11-06
ORD - TLH
First | 2 Stops
From 25,500 Pts + $5.6
Premium cabin
2026-11-06
ORD - TLH
First | 2 Stops
From 25,500 Pts + $5.6
Premium cabin
2026-11-09
ORD - TLH
First | 1 Stop | 5 left
From 35,000 Pts + $31.2
Selected hotels for your next stay
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Frequently Asked Questions
The cheapest route from Chicago to Tallahassee 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 Tallahassee.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Tallahassee.
Chicago and Tallahassee are about 819 miles (1,318 km) apart in a straight line.
Flying the 819-mile straight-line distance takes about 2h 15m in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Tallahassee is 1 hour ahead of Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Tallahassee: Tallahassee Regional (TLH).
Travelers searching this route also look at other popular routes into Tallahassee, plus the return trip when we track it. Fares and award space change daily.
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