Cheap Flights from Chicago to Jacksonville
Looking for cheap flights from Chicago to Jacksonville? 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 Jacksonville vary by season and date, but economy flights can start around 7,500–13,000 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 Jacksonville for specific travel dates.
2026-04-15
ORD - JAX
Economy | Non stop
From 13,000 Pts + $5.6
2026-04-15
ORD - JAX
Economy | Non stop | 9+ left
From 12,500 Pts + $10.2
2026-04-16
ORD - JAX
Economy | 1 Stop
From 13,000 Pts + $5.6
2026-04-17
ORD - JAX
Economy | Non stop
From 13,000 Pts + $5.6
2026-04-17
ORD - JAX
Economy | Non stop | 9+ left
From 12,500 Pts + $10.2
2026-04-18
ORD - JAX
Economy | Non stop | 9+ left
From 7,500 Pts + $18.1
Premium cabin flights from Chicago to Jacksonville
Premium cabin
2026-04-15
ORD - JAX
First | Non stop
From 24,000 Pts + $5.6
Premium cabin
2026-04-16
ORD - JAX
First | 1 Stop
From 24,000 Pts + $11.2
Premium cabin
2026-04-17
ORD - JAX
First | Non stop
From 24,000 Pts + $5.6
Premium cabin
2026-04-18
ORD - JAX
First | Non stop | 4 left
From 15,000 Pts + $18.1
Premium cabin
2026-04-18
ORD - JAX
First | Non stop
From 24,000 Pts + $5.6
Premium cabin
2026-04-19
ORD - JAX
First | Non stop
From 21,500 Pts + $5.6
Selected hotels for your next stay
Jacksonville (United States)
Hotel Indigo Jacksonville-Deerwood Park
From 23,000 Pts or $156
Amelia Island (USA)
The Ritz-Carlton, Amelia Island
From Pts or $1175
St. Augustine, FL (USA)
Casa Monica Resort & Spa, Autograph Collection
From Pts or $264
Frequently Asked Questions
The cheapest route from Chicago to Jacksonville 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 Jacksonville.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Jacksonville.
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