$98 Flight Deals from Jacksonville to Chicago

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... and +100s more

Incredible Deals

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Price Drop Deals Near You

Chicago

33% Price Drop

Jul 11

JAX

4 days

Jul 15

ORD

$294

now only

^$197

Round Trip

26% Price Drop

Jul 5

JAX

4 days

Jul 9

MDW

$332

now only

^$246

Round Trip

Chicago

33% Price Drop

Jul 23

JAX

5 days

Jul 28

ORD

$294

now only

^$197

Round Trip

Chicago

33% Price Drop

Jul 24

JAX

4 days

Jul 28

ORD

$294

now only

^$197

Round Trip

Chicago

30% Price Drop

Jul 18

JAX

5 days

Jul 23

ORD

$294

now only

^$207

Round Trip

Chicago

26% Price Drop

Jul 2

JAX

3 days

Jul 5

ORD

$294

now only

^$217

Round Trip

Chicago

23% Price Drop

Aug 22

JAX

3 days

Aug 25

ORD

$294

now only

^$225

Round Trip

Chicago

23% Price Drop

Aug 14

JAX

4 days

Aug 18

ORD

$294

now only

^$226

Round Trip

Chicago

23% Price Drop

Aug 29

JAX

3 days

Sep 1

ORD

$294

now only

^$226

Round Trip

Chicago

21% Price Drop

Jul 11

JAX

3 days

Jul 14

ORD

$294

now only

^$232

Round Trip

Stops

Nonstop
from $280
Up to 1 stop
$315

Airlines

American Airlines
$280
JetBlue
$497
United Airlines
$360

Cabin Class

Economy
$280

Departure Airports

Jacksonville International Airport
$280

Arrival Airports

Chicago O Hare Airport
$280

Layover Airports

Charlotte Douglas International Airport
$315
General Edward Lawrence Logan International Airport
$497
New York John F Kennedy Airport
$497
Newark Liberty Airport
$448
Philadelphia International Airport
$356
Reagan Washington National Airport
$315
Washington Dulles Airport
$370

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

EXPRESS DEAL

BUDGET FRIENDLY

You’re guaranteed to get one of these airlines:

Delta

Alaska

United

American

JAX ORD

Sep 12 - Sep 15 ‧ Economy

^$197

Round Trip

BUDGET FRIENDLY

You’re guaranteed to get one of these airlines:

Delta

Alaska

United

American

JAX ORD

Jul 19 - Jul 29 ‧ Economy

^$198

Round Trip

BUDGET FRIENDLY

You’re guaranteed to get one of these airlines:

Delta

Alaska

United

American

JAX ORD

Sep 05 - Sep 07 ‧ Economy

^$200

Round Trip

BUDGET FRIENDLY

You’re guaranteed to get one of these airlines:

Delta

Alaska

United

American

JAX ORD

Jul 18 - Jul 25 ‧ Economy

^$215

Round Trip

BUDGET FRIENDLY

You’re guaranteed to get one of these airlines:

Delta

Alaska

United

American

JAX ORD

Jul 04 - Jul 08 ‧ Economy

^$264

Round Trip

BUDGET FRIENDLY

You’re guaranteed to get one of these airlines:

Delta

Alaska

United

American

JAX ORD

Jun 28 ‧ Economy

^$176

One Way

American Airlines

07/25/25

7:00am

JAX

2h 38m

Direct

07/25/25

8:38am

ORD

American Airlines

08/01/25

8:05am

ORD

2h 19m

Direct

08/01/25

11:24am

JAX

^$280

American Airlines

07/25/25

12:14pm

JAX

2h 46m

Direct

07/25/25

2:00pm

ORD

American Airlines

08/01/25

8:05am

ORD

2h 19m

Direct

08/01/25

11:24am

JAX

^$280

American Airlines

07/25/25

8:30pm

JAX

4h 27m

CLT

07/25/25

11:57pm

ORD

American Airlines

08/01/25

8:05am

ORD

2h 19m

Direct

08/01/25

11:24am

JAX

^$315

American Airlines

07/25/25

11:06am

JAX

7h 31m

CLT

07/25/25

5:37pm

ORD

American Airlines

08/01/25

8:05am

ORD

2h 19m

Direct

08/01/25

11:24am

JAX

^$315

American Airlines

07/25/25

7:01pm

JAX

5h 28m

DCA

07/25/25

11:29pm

ORD

American Airlines

08/01/25

8:05am

ORD

2h 19m

Direct

08/01/25

11:24am

JAX

^$315

American Airlines

07/25/25

6:11pm

JAX

6h 46m

CLT

07/25/25

11:57pm

ORD

American Airlines

08/01/25

8:05am

ORD

2h 19m

Direct

08/01/25

11:24am

JAX

^$315

American Airlines

07/25/25

6:11pm

JAX

4h 20m

CLT

07/25/25

9:31pm

ORD

American Airlines

08/01/25

8:05am

ORD

2h 19m

Direct

08/01/25

11:24am

JAX

^$315

American Airlines

07/25/25

7:00am

JAX

2h 38m

Direct

07/25/25

8:38am

ORD

American Airlines

08/01/25

6:52pm

ORD

2h 30m

Direct

08/01/25

10:22pm

JAX

^$346

American Airlines

07/25/25

12:14pm

JAX

2h 46m

Direct

07/25/25

2:00pm

ORD

American Airlines

08/01/25

6:52pm

ORD

2h 30m

Direct

08/01/25

10:22pm

JAX

^$346

American Airlines

07/25/25

12:14pm

JAX

2h 46m

Direct

07/25/25

2:00pm

ORD

American Airlines

08/01/25

5:00am

ORD

5h 2m

PHL

08/01/25

11:02am

JAX

^$356

American Airlines

07/25/25

7:00am

JAX

2h 38m

Direct

07/25/25

8:38am

ORD

American Airlines

08/01/25

5:00am

ORD

5h 2m

PHL

08/01/25

11:02am

JAX

^$356

United Airlines

07/25/25

8:00am

JAX

2h 45m

Direct

07/25/25

9:45am

ORD

United Airlines

08/01/25

7:00am

ORD

2h 39m

Direct

08/01/25

10:39am

JAX

^$360

United Airlines

07/25/25

4:30pm

JAX

2h 45m

Direct

07/25/25

6:15pm

ORD

United Airlines

08/01/25

11:59am

ORD

2h 34m

Direct

08/01/25

3:33pm

JAX

^$360

United Airlines

07/25/25

4:30pm

JAX

2h 45m

Direct

07/25/25

6:15pm

ORD

United Airlines

08/01/25

7:35pm

ORD

2h 36m

Direct

08/01/25

11:11pm

JAX

^$360

United Airlines

07/25/25

8:00am

JAX

2h 45m

Direct

07/25/25

9:45am

ORD

United Airlines

08/01/25

11:59am

ORD

2h 34m

Direct

08/01/25

3:33pm

JAX

^$360

United Airlines

07/25/25

6:55pm

JAX

5h 35m

IAD

07/25/25

11:30pm

ORD

United Airlines

08/01/25

7:00am

ORD

2h 39m

Direct

08/01/25

10:39am

JAX

^$370

United Airlines

07/25/25

6:55pm

JAX

5h 35m

IAD

07/25/25

11:30pm

ORD

United Airlines

08/01/25

11:59am

ORD

2h 34m

Direct

08/01/25

3:33pm

JAX

^$370

United Airlines

07/25/25

6:55pm

JAX

5h 35m

IAD

07/25/25

11:30pm

ORD

United Airlines

08/01/25

7:35pm

ORD

2h 36m

Direct

08/01/25

11:11pm

JAX

^$370

American Airlines

07/25/25

7:01pm

JAX

5h 28m

DCA

07/25/25

11:29pm

ORD

American Airlines

08/01/25

6:52pm

ORD

2h 30m

Direct

08/01/25

10:22pm

JAX

^$381

American Airlines

07/25/25

7:01pm

JAX

5h 28m

DCA

07/25/25

11:29pm

ORD

American Airlines

08/01/25

5:00am

ORD

5h 2m

PHL

08/01/25

11:02am

JAX

^$391

American Airlines

07/25/25

6:11pm

JAX

4h 20m

CLT

07/25/25

9:31pm

ORD

American Airlines

08/01/25

5:00am

ORD

5h 2m

PHL

08/01/25

11:02am

JAX

^$391

American Airlines

07/25/25

7:01pm

JAX

5h 28m

DCA

07/25/25

11:29pm

ORD

American Airlines

08/01/25

5:15am

ORD

4h 1m

CLT

08/01/25

10:16am

JAX

^$391

American Airlines

07/25/25

7:01pm

JAX

5h 28m

DCA

07/25/25

11:29pm

ORD

American Airlines

08/01/25

7:05am

ORD

CLT

08/01/25

1:05pm

JAX

^$391

United Airlines

07/25/25

6:56pm

JAX

13h 42m

EWR

07/26/25

7:38am

ORD

United Airlines

08/01/25

11:59am

ORD

2h 34m

Direct

08/01/25

3:33pm

JAX

^$448

United Airlines

07/25/25

6:56pm

JAX

14h 43m

EWR

07/26/25

8:39am

ORD

United Airlines

08/01/25

11:59am

ORD

2h 34m

Direct

08/01/25

3:33pm

JAX

^$448

United Airlines

07/25/25

6:56pm

JAX

14h 43m

EWR

07/26/25

8:39am

ORD

United Airlines

08/01/25

7:00am

ORD

2h 39m

Direct

08/01/25

10:39am

JAX

^$448

United Airlines

07/25/25

6:56pm

JAX

14h 43m

EWR

07/26/25

8:39am

ORD

United Airlines

08/01/25

7:35pm

ORD

2h 36m

Direct

08/01/25

11:11pm

JAX

^$448

United Airlines

07/25/25

4:30pm

JAX

2h 45m

Direct

07/25/25

6:15pm

ORD

United Airlines

08/01/25

8:52am

ORD

5h 2m

IAD

08/01/25

2:54pm

JAX

^$456

JetBlue

07/25/25

9:55am

JAX

6h 37m

BOS

07/25/25

3:32pm

ORD

JetBlue

08/01/25

12:06pm

ORD

7h 45m

JFK

08/01/25

8:51pm

JAX

^$497

JetBlue

07/25/25

9:55am

JAX

6h 37m

BOS

07/25/25

3:32pm

ORD

JetBlue

08/01/25

6:16am

ORD

6h 13m

JFK

08/01/25

1:29pm

JAX

^$497

Top Deals on flights from Jacksonville to Chicago

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

American Airlines

Dec 9

3:50pm

JAX

1h 47m

Direct

Dec 9

5:37pm

ORD

as low as

^$98

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

Sep 9

6:20am

JAX

5h 56m

ATL

Sep 9

12:16pm

ORD

as low as

^$100

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

Sep 20

11:50am

JAX

4h 44m

DTW

Sep 20

4:34pm

ORD

as low as

^$100

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

Sep 13

6:00am

JAX

7h 14m

LGA

Sep 13

1:14pm

ORD

as low as

^$100

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

Sep 6

5:01pm

JAX

4h 11m

ATL

Sep 6

9:12pm

MDW

as low as

^$100

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

JetBlue

Aug 24

6:20am

JAX

4h 58m

JFK

Aug 24

11:18am

ORD

as low as

^$121

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

Aug 31

2:30pm

JAX

7h 5m

MSP

Aug 31

9:35pm

ORD

as low as

^$122

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

United Airlines

Oct 7

11:22am

JAX

1h 45m

Direct

Oct 7

1:07pm

ORD

as low as

^$125

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

American Airlines

Sep 18

6:34pm

JAX

5h 5m

CLT

Sep 18

11:39pm

ORD

as low as

^$133

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

American Airlines

Dec 9

12:02pm

JAX

5h 30m

DFW

Dec 9

5:32pm

ORD

as low as

^$133

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

United Airlines

Aug 20

1:25pm

JAX

IAD

Aug 20

6:25pm

ORD

as low as

^$135

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

Sep 18

7:30pm

JAX

20h 55m

BNA

Sep 19

4:25pm

ORD

as low as

^$146

Frequently Asked Questions

What is the cheapest flight from Jacksonville to Chicago?

The cheapest flight is with American Airlines, a non-stop flight from Jacksonville International Airport to Chicago O'Hare Airport for $280, with a flight time of 2 hours 38 minutes.

What are all possible destination arrival airports?

The possible destination arrival airport for your route is Chicago O'Hare Airport.

What is the time difference between destination and arrival?

The time difference between Jacksonville, FL and Chicago, IL is one hour, with Chicago being one hour behind Jacksonville.

Is there a direct flight from Jacksonville to Chicago?

Yes, there are direct flights from Jacksonville International Airport to Chicago O'Hare Airport. American Airlines offers a non-stop flight priced at $280, with a flight time of 2 hours and 38 minutes. United Airlines also provides a non-stop flight for $360, taking 2 hours and 45 minutes.

Are there convenient layover flights from Jacksonville to Chicago?

Yes, convenient 1 stop flights are available. American Airlines offers a flight for $315 (4h 20m, layover: Charlotte), United Airlines for $370 (5h 35m, layover: Washington), and JetBlue for $497 (6h 37m, layover: Logan).

What are the most convenient layover airports for the flight?

The most convenient layover airports for your flight are Charlotte Douglas International Airport with American Airlines, and Washington Dulles Airport with United Airlines.

Flights to Chicago

Top Destinations

Origins

Return flights

Cabin Class

Flight Deals from Jacksonville to Chicago from $98

Price Drop Deals Near You

Stops

Airlines

Cabin Class

Departure Airports

Arrival Airports

Layover Airports

Best Price. GUARANTEED.

Top Deals on flights from Jacksonville to Chicago

Frequently Asked Questions

Flights to Chicago