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Flight Deals from Chicago to Jacksonville from $138

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Bundle + Save

Top flight deals from leading airlines:

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Incredible Deals

Save up to 50% on select flights with Priceline

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Save an average of $240 per person when bundling your flight and hotel together with Priceline

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Price Drop Deals Near You

Stops

  • Nonstop
    from $306
  • Up to 1 stop
    $256
  • Up to 2 stops
    $353

Airlines

  • American Airlines
    $306
  • Delta Air Lines
    $256
  • JetBlue
    $318
  • Southwest Airlines
    $303
  • Sun Country Airlines
    $356
  • United Airlines
    $306

Cabin Class

  • Economy
    $256

Departure Airports

  • Chicago Midway Airport
    $256
  • Chicago O Hare Airport
    $256

Arrival Airports

  • Jacksonville International Airport
    $256

Layover Airports

  • Baltimore/Washington International Thurgood Marshall Airport
    $353
  • Charlotte Douglas International Airport
    $356
  • Dallas Fort Worth International Airport
    $366
  • Detroit Metropolitan Airport
    $256
  • Hartsfield Jackson Atlanta International Airport
    $256
  • John Glenn Columbus International Airport
    $353
  • Miami International Airport
    $316
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $296
  • Nashville International Airport
    $303
  • New York John F Kennedy Airport
    $318
  • New York LaGuardia Airport
    $386
  • Philadelphia International Airport
    $426
  • Reagan Washington National Airport
    $316
  • St Louis Lambert International Airport
    $376
  • Washington Dulles Airport
    $316

Best Price. GUARANTEED.

Exclusively for Priceline Members
Tired of searching? Book now!
We'll refund the difference if you find a lower price.

BUNDLE & SAVE

Book a flight & hotel together for extra savings.

On average save $240 per traveler
Delta Air Lines Logo
Delta Air Lines

07/29/25

ORD
7h 44m
ATL

07/29/25

JAX
Delta Air Lines Logo
Delta Air Lines

08/05/25

JAX
5h 10m
ATL

08/06/25

ORD
$256
Delta Air Lines Logo
Delta Air Lines

07/30/25

MDW
7h 40m
DTW

07/30/25

JAX
Delta Air Lines Logo
Delta Air Lines

08/06/25

JAX
4h 35m
ATL

08/06/25

MDW
$256
Delta Air Lines Logo
Delta Air Lines

07/19/25

ORD
6h 32m
ATL

07/19/25

JAX
Delta Air Lines Logo
Delta Air Lines

07/26/25

JAX
4h 50m
MSP

07/26/25

ORD
$296
Delta Air Lines Logo
Delta Air Lines

07/23/25

MDW
7h 40m
DTW

07/23/25

JAX
Delta Air Lines Logo
Delta Air Lines

07/30/25

JAX
4h 35m
ATL

07/30/25

MDW
$296
Southwest Airlines Logo
Southwest Airlines

07/23/25

MDW
3h 15m
Direct

07/23/25

JAX
Southwest Airlines Logo
Southwest Airlines

07/27/25

JAX
24h 20m
BNA

07/28/25

MDW
$303
American Airlines Logo
American Airlines

07/29/25

ORD
3h 30m
Direct

07/29/25

JAX
American Airlines Logo
American Airlines

08/05/25

JAX
1h 46m
Direct

08/05/25

ORD
$306
United Airlines Logo
United Airlines

07/29/25

ORD
3h 34m
Direct

07/29/25

JAX
United Airlines Logo
United Airlines

08/05/25

JAX
1h 45m
Direct

08/05/25

ORD
$306
American Airlines Logo
American Airlines

07/30/25

ORD
3h 30m
Direct

07/30/25

JAX
American Airlines Logo
American Airlines

08/06/25

JAX
1h 39m
Direct

08/06/25

ORD
$306
United Airlines Logo
United Airlines

07/30/25

ORD
3h 34m
Direct

07/30/25

JAX
United Airlines Logo
United Airlines

08/06/25

JAX
1h 45m
Direct

08/06/25

ORD
$306
American Airlines Logo
American Airlines

07/30/25

ORD
8h 12m
DCA

07/30/25

JAX
American Airlines Logo
American Airlines

08/06/25

JAX
1h 39m
Direct

08/06/25

ORD
$316
United Airlines Logo
United Airlines

07/29/25

ORD
3h 39m
Direct

07/29/25

JAX
United Airlines Logo
United Airlines

08/05/25

JAX
4h 35m
IAD

08/05/25

ORD
$316
American Airlines Logo
American Airlines

07/29/25

ORD
8h 33m
MIA

07/29/25

JAX
American Airlines Logo
American Airlines

08/05/25

JAX
1h 38m
Direct

08/05/25

ORD
$316
Southwest Airlines Logo
Southwest Airlines

07/23/25

MDW
3h 15m
Direct

07/23/25

JAX
Southwest Airlines Logo
Southwest Airlines

07/27/25

JAX
1h 25m
Direct

07/27/25

MDW
$316
JetBlue Logo
JetBlue

07/17/25

ORD
8h 45m
JFK

07/17/25

JAX
JetBlue Logo
JetBlue

07/24/25

JAX
8h 4m
JFK

07/24/25

ORD
$318
Southwest Airlines Logo
Southwest Airlines

07/23/25

MDW
25h 25m
BNA

07/24/25

JAX
Southwest Airlines Logo
Southwest Airlines

07/27/25

JAX
24h 20m
BNA

07/28/25

MDW
$330
JetBlue Logo
JetBlue

07/30/25

ORD
7h 12m
JFK

07/30/25

JAX
JetBlue Logo
JetBlue

08/06/25

JAX
7h 24m
JFK

08/06/25

ORD
$337
Southwest Airlines Logo
Southwest Airlines

07/23/25

MDW
10h 30m
CMH
BWI

07/23/25

JAX
Southwest Airlines Logo
Southwest Airlines

07/27/25

JAX
24h 20m
BNA

07/28/25

MDW
$353
Sun Country Airlines Logo
Sun Country Airlines

07/24/25

ORD
17h 24m
MSP

07/25/25

JAX
Sun Country Airlines Logo
Sun Country Airlines

07/28/25

JAX
22h 13m
MSP

07/29/25

ORD
$356
American Airlines Logo
American Airlines

07/15/25

ORD
8h 17m
MIA

07/15/25

JAX
American Airlines Logo
American Airlines

07/22/25

JAX
1h 46m
Direct

07/22/25

ORD
$356
American Airlines Logo
American Airlines

07/23/25

ORD
7h 25m
CLT

07/24/25

JAX
American Airlines Logo
American Airlines

07/30/25

JAX
1h 46m
Direct

07/30/25

ORD
$356
United Airlines Logo
United Airlines

07/30/25

ORD
3h 34m
Direct

07/30/25

JAX
United Airlines Logo
United Airlines

08/02/25

JAX
4h 35m
IAD

08/02/25

ORD
$356
American Airlines Logo
American Airlines

07/04/25

ORD
7h 24m
DCA

07/04/25

JAX
American Airlines Logo
American Airlines

07/15/25

JAX
1h 38m
Direct

07/15/25

ORD
$356
American Airlines Logo
American Airlines

07/16/25

ORD
5h 58m
CLT

07/16/25

JAX
American Airlines Logo
American Airlines

07/23/25

JAX
1h 38m
Direct

07/23/25

ORD
$356
American Airlines Logo
American Airlines

07/19/25

ORD
5h 59m
CLT

07/20/25

JAX
American Airlines Logo
American Airlines

07/26/25

JAX
6h 40m
DFW

07/26/25

ORD
$366
American Airlines Logo
American Airlines

07/04/25

ORD
5h 37m
DCA

07/04/25

JAX
American Airlines Logo
American Airlines

07/15/25

JAX
5h 56m
DFW

07/15/25

ORD
$366
Southwest Airlines Logo
Southwest Airlines

07/24/25

MDW
3h 15m
Direct

07/24/25

JAX
Southwest Airlines Logo
Southwest Airlines

07/28/25

JAX
10h 40m
BNA
STL

07/29/25

MDW
$376
Southwest Airlines Logo
Southwest Airlines

07/24/25

MDW
11h 50m
BNA

07/24/25

JAX
Southwest Airlines Logo
Southwest Airlines

07/28/25

JAX
10h 40m
BNA
STL

07/29/25

MDW
$381
Delta Air Lines Logo
Delta Air Lines

08/01/25

MDW
7h 30m
ATL

08/01/25

JAX
Delta Air Lines Logo
Delta Air Lines

08/08/25

JAX
7h 3m
LGA

08/08/25

MDW
$386
American Airlines Logo
American Airlines

07/08/25

ORD
7h 48m
CLT

07/08/25

JAX
American Airlines Logo
American Airlines

07/11/25

JAX
5h 22m
PHL

07/11/25

ORD
$426
American Airlines Logo
American Airlines

07/25/25

ORD
7h 50m
PHL

07/25/25

JAX
American Airlines Logo
American Airlines

07/31/25

JAX
1h 46m
Direct

07/31/25

ORD
$436

Top Deals on flights from Chicago to Jacksonville

Chicago, US (CHI) - Jacksonville, US (JAX)

Southwest Airlines Logo
Southwest Airlines

Jul 23

MDW
3h 15m
Direct

Jul 23

JAX

as low as

$138

Chicago, US (CHI) - Jacksonville, US (JAX)

Delta Air Lines Logo
Delta Air Lines

Jul 23

MDW
7h 40m
DTW

Jul 23

JAX

as low as

$148

Chicago, US (CHI) - Jacksonville, US (JAX)

Delta Air Lines Logo
Delta Air Lines

Jul 19

ORD
4h 54m
ATL

Jul 19

JAX

as low as

$148

Chicago, US (CHI) - Jacksonville, US (JAX)

Delta Air Lines Logo
Delta Air Lines

Jul 4

MDW
6h 9m
ATL

Jul 4

JAX

as low as

$148

Chicago, US (CHI) - Jacksonville, US (JAX)

Southwest Airlines Logo
Southwest Airlines

Jul 23

MDW
25h 25m
BNA

Jul 24

JAX

as low as

$170

Chicago, US (CHI) - Jacksonville, US (JAX)

United Airlines Logo
United Airlines

Jul 15

ORD
3h 34m
Direct

Jul 15

JAX

as low as

$173

Chicago, US (CHI) - Jacksonville, US (JAX)

American Airlines Logo
American Airlines

Jul 23

ORD
3h 19m
Direct

Jul 23

JAX

as low as

$173

Chicago, US (CHI) - Jacksonville, US (JAX)

United Airlines Logo
United Airlines

Jul 4

ORD
6h 2m
IAD

Jul 4

JAX

as low as

$183

Chicago, US (CHI) - Jacksonville, US (JAX)

American Airlines Logo
American Airlines

Jul 23

ORD
5h 1m
CLT

Jul 23

JAX

as low as

$183

Chicago, US (CHI) - Jacksonville, US (JAX)

Southwest Airlines Logo
Southwest Airlines

Jul 23

MDW
7h 55m
PIT
BWI

Jul 23

JAX

as low as

$188

Chicago, US (CHI) - Jacksonville, US (JAX)

Southwest Airlines Logo
Southwest Airlines

Jul 24

MDW
10h 15m
MCO
HOU

Jul 24

JAX

as low as

$193

Chicago, US (CHI) - Jacksonville, US (JAX)

Sun Country Airlines Logo
Sun Country Airlines

Jul 24

ORD
17h 24m
MSP

Jul 25

JAX

as low as

$213